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CAS

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4-Hydroxyquinazoline, also known as 4-HQN, is an organic compound with the chemical formula C8H6N2O. It is an off-white to light beige crystalline powder that has been found to possess various biological activities, including anti-microbial, anti-carcinogenic, and anti-inflammatory properties. The quinazoline moiety in its structure contributes to its observed effects, making it a compound of interest for pharmaceutical and medical applications.

491-36-1

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491-36-1 Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxyquinazoline is used as an inhibitor for poly(ADP-ribose) polymerase (PARP), specifically targeting PARP-1 with an IC50 of 9.5 μM. It displays mixed inhibition with respect to NAD+ and has been shown to protect against ischemia-reperfusion induced reactive oxygen species (ROS) production, mitochondrial and cell damage in rat hearts.
Used in Anticancer Applications:
4-Hydroxyquinazoline exhibits anti-carcinogenic activity due to its quinazoline moiety. It has the potential to be used in the development of anti-cancer drugs, targeting various types of cancer by modulating oncological signaling pathways.
Used in Anti-inflammatory Applications:
4-Hydroxyquinazoline is used as an anti-inflammatory agent in LPS-induced endotoxic mice in vivo. It has been shown to decrease the activation of transcription factors NF-κB and AP-1, which play a crucial role in the regulation of immune responses and inflammation.
Used in Mitochondrial Protection:
4-HQN demonstrates protective effects against ischemia-reperfusion-induced increase of protein oxidation, single-strand DNA breaks, lipid peroxidation, and mitochondrial reactive oxygen species production in the reperfusion period. This makes it a potential candidate for the development of therapies aimed at protecting mitochondria and reducing cell damage during ischemic events.

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 1669, 1951 DOI: 10.1021/jo50005a003

Flammability and Explosibility

Notclassified

Biological Activity

Inhibitor of poly(ADP-ribose) polymerase (PARP) (IC 50 = 9.5 μ M); displays mixed inhibition with respect to NAD + . Protective against ischemia-reperfusion induced ROS production, and subsequent mitochondrial and cell damage in rat heart. Anti-inflammatory in LPS-induced endotoxic mice in vivo ; decreases NF- κ B and AP-1 activation.

References

1) Banasil?et al. (1992),?Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase;? J. Biol. Chem.,?267?1569 2) Halmosi?et al. (2001),?Effect of poly(ADP-ribose) polymerase inhibitors on the ischemia-reperfusion-induced oxidative cell damage and mitochondrial metabolism in Langendorff heart perfusion system.? Clin. Mol. Pharmacol.,?59?1497 3) Veres?et al. (2004),?Regulation of kinase cascades and transcription factors by a poly(ADP-ribose) polymerase-1 inhibitor, 4-hydroxyquinazoline, in lipopolysaccharide-induced inflammation in mice;? J. Pharmacol. Exp. Ther.,?310?247

Check Digit Verification of cas no

The CAS Registry Mumber 491-36-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 491-36:
(5*4)+(4*9)+(3*1)+(2*3)+(1*6)=71
71 % 10 = 1
So 491-36-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)

491-36-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A17129)  4-Hydroxyquinazoline, 98%   

  • 491-36-1

  • 10g

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (A17129)  4-Hydroxyquinazoline, 98%   

  • 491-36-1

  • 50g

  • 1189.0CNY

  • Detail
  • Aldrich

  • (H57807)  4-Hydroxyquinazoline  98%

  • 491-36-1

  • H57807-5G

  • 384.93CNY

  • Detail

491-36-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Hydroxyquinazoline

1.2 Other means of identification

Product number -
Other names Quinazolone,4

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:491-36-1 SDS

491-36-1Synthetic route

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

trimethyl orthoformate
149-73-5

trimethyl orthoformate

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium acetate In methanol at 120℃; for 3h;98%
formic acid
64-18-6

formic acid

anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
for 8h; Heating;97%
With iodine; oxygen; dimethyl sulfoxide at 110℃; for 4h;55%
anthranilic acid amide
28144-70-9

anthranilic acid amide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With Imidazole hydrochloride at 150℃; for 13h; Temperature;97%
With toluene-4-sulfonic acid at 120℃; for 10h; Sealed tube;87%
With Triethoxysilane; carbon dioxide; tris(pentafluorophenyl)borate at 120℃; for 24h;99 %Spectr.
anthranilic acid amide
28144-70-9

anthranilic acid amide

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
In ethanol for 43h; Heating;96%
With antimony(III) chloride In neat (no solvent) for 0.0333333h; Solvent; Microwave irradiation; Green chemistry;95%
With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate at 45 - 46℃; for 0.416667h; Ionic liquid; Sonication; neat (no solvent); chemoselective reaction;91%
isatoic anhydride
118-48-9

isatoic anhydride

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium hydroxide; Glyoxilic acid In water at 110 - 120℃; for 0.133333h;96%
With aluminum potassium sulfate dodecahydrate; ammonium acetate; orthoformic acid triethyl ester for 0.1h; Microwave irradiation; neat (no solvent);92%
With formamidine acetic acid In ethanol for 3h; Heating;81%
With formamide at 120 - 125℃; for 1.5h;81%
anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With acetic acid; diethylamine at 150℃; for 2h; Product distribution / selectivity;96%
With antimony(III) chloride for 0.0833333h; Niementowski Quinazolone Synthesis; Microwave irradiation; Green chemistry;95%
With ytterbium(III) triflate In 1,3,5-trimethyl-benzene at 120℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;79%
With acetic acid
4-amino-o-xylene
95-64-7

4-amino-o-xylene

anthranilic acid amide
28144-70-9

anthranilic acid amide

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

A

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

B

N-(3,4-dimethylphenyl)quinazolin-4-amine

N-(3,4-dimethylphenyl)quinazolin-4-amine

Conditions
ConditionsYield
With Preyssler heteropolyacid In acetonitrile for 2h; Reflux;A n/a
B 96%
With H6[PMo9V3O40] In acetonitrile for 2h; Reflux;A 5%
B 95%
hydrogen cyanide
74-90-8

hydrogen cyanide

o-iodobenzamide
3930-83-4

o-iodobenzamide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium hydroxide; palladium dichloride at 90℃; for 0.166667h; Microwave irradiation; Green chemistry;96%
hydrogen cyanide
74-90-8

hydrogen cyanide

2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium hydroxide; palladium dichloride at 90℃; for 0.166667h; Microwave irradiation; Green chemistry;96%
anthranilic acid
118-92-3

anthranilic acid

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
Heating;95.4%
95.4%
for 0.25h; Irradiation;95%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With diphenyl-phosphinic acid; oxygen In 1,4-dioxane at 130℃; under 760.051 Torr; for 18h; Schlenk technique;95%
p-toluidine
106-49-0

p-toluidine

anthranilic acid amide
28144-70-9

anthranilic acid amide

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

A

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

B

N-(p-tolyl)quinazolin-4-amine
34923-96-1

N-(p-tolyl)quinazolin-4-amine

Conditions
ConditionsYield
With Preyssler heteropolyacid In acetonitrile for 2h; Reflux;A n/a
B 94%
With H6[PMo9V3O40] In acetonitrile for 2h; Reflux;A 7%
B 93%
4-amino-o-xylene
95-64-7

4-amino-o-xylene

anthranilic acid amide
28144-70-9

anthranilic acid amide

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

B

N-(3,4-dimethylphenyl)quinazolin-4-amine

N-(3,4-dimethylphenyl)quinazolin-4-amine

Conditions
ConditionsYield
With H6[PMo9V3O40] In acetonitrile Reflux;A n/a
B 94%
2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

formamidine hydrochloride
6313-33-3

formamidine hydrochloride

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With copper 8-hydroxyquinolinate; sodium hydroxide In water at 100℃; for 0.5h; Microwave irradiation;94%
hydrogen cyanide
74-90-8

hydrogen cyanide

2-Bromobenzamide
4001-73-4

2-Bromobenzamide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium hydroxide; palladium dichloride at 90℃; for 0.166667h; Microwave irradiation; Green chemistry;94%
hydrogen cyanide
74-90-8

hydrogen cyanide

2-bromobenzoic-acid
88-65-3

2-bromobenzoic-acid

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium hydroxide; palladium dichloride at 90℃; for 0.166667h; Microwave irradiation; Green chemistry;94%
anthranilic acid
118-92-3

anthranilic acid

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium acetate for 0.1h; microwave irradiation;93%
With ammonium acetate; antimony(III) chloride In neat (no solvent) for 0.0833333h; Microwave irradiation; Green chemistry;93%
With ammonium acetate In ethanol at 110℃; for 0.333333h; Microwave irradiation;
formaldehyd
50-00-0

formaldehyd

anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With iron(III) chloride In water for 1h; Heating;92%
With [Cp*Ir(2,2′-bpyO)(H2O)]; caesium carbonate In toluene at 130℃; for 2h; Microwave irradiation;82%
With bis(acetylacetonate)oxovanadium; oxygen In 1,2-dichloro-ethane at 80℃; under 760.051 Torr; for 6h;80%
methanol
67-56-1

methanol

anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With oxygen; copper(II) acetate monohydrate; caesium carbonate at 110℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Time;92%
With [Cp*Ir(2,2′-bpyO)(H2O)]; caesium carbonate at 130℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Microwave irradiation; Green chemistry;88%
With [Cp*Ir(2,2'-bpyO)(H2O)]; caesium carbonate at 130℃; for 2h; Temperature; Reagent/catalyst; Microwave irradiation; Inert atmosphere;88%
quinazoline
253-82-7

quinazoline

benzaldehyde
100-52-7

benzaldehyde

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With N-hydroxyphthalimide; cobalt(III) acetylacetonate; cobalt acetylacetonate In benzonitrile; trifluoroacetic acid at 70℃; for 12h; Product distribution; Further Variations:; Reagents;91%
p-toluidine
106-49-0

p-toluidine

anthranilic acid amide
28144-70-9

anthranilic acid amide

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

B

N-(p-tolyl)quinazolin-4-amine
34923-96-1

N-(p-tolyl)quinazolin-4-amine

Conditions
ConditionsYield
With H6[PMo9V3O40] In acetonitrile Reflux;A n/a
B 91%
anthranilic acid amide
28144-70-9

anthranilic acid amide

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

aniline
62-53-3

aniline

A

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

B

4-(phenylamino)quinazoline
34923-95-0

4-(phenylamino)quinazoline

Conditions
ConditionsYield
With H6[PMo9V3O40] In acetonitrile for 2h; Reflux;A 9%
B 91%
With Preyssler heteropolyacid In acetonitrile for 2h; Reflux;A n/a
B 91%
isatoic anhydride
118-48-9

isatoic anhydride

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With ammonium acetate In neat (no solvent) at 120℃; for 5h; Temperature; Green chemistry;91%
With ammonium acetate; Thiamine hydrochloride In ethanol for 4h; Reflux;85%
2,3-dihydro-4(1H)-quinazolinone
5632-36-0

2,3-dihydro-4(1H)-quinazolinone

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With copper(l) iodide; oxygen; caesium carbonate at 20℃; for 10h; Reagent/catalyst; Irradiation;91%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform at 20℃; for 1h; Schlenk technique; Sealed tube;11.1 mg
With tetrabutylammonium perchlorate; toluene-4-sulfonic acid In acetonitrile at 20℃; for 1.5h; Electrolysis;40 mg
With cobalt(II) nitrate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; caesium carbonate In methanol at 150℃; for 3h; Reagent/catalyst; Inert atmosphere; Sealed tube;
formamidine acetic acid
3473-63-0

formamidine acetic acid

anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
In ethanol for 16h; Reflux;90.7%
anthranilic acid amide
28144-70-9

anthranilic acid amide

4,4-dimethyl-Δ2-oxazolinium chloride
90965-28-9

4,4-dimethyl-Δ2-oxazolinium chloride

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h; Heating;90%
4-chloro-aniline
106-47-8

4-chloro-aniline

anthranilic acid amide
28144-70-9

anthranilic acid amide

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

A

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

B

N-(4-chlorophenyl)quinazolin-4-amine

N-(4-chlorophenyl)quinazolin-4-amine

Conditions
ConditionsYield
With Preyssler heteropolyacid In acetonitrile for 2h; Reflux;A n/a
B 90%
With H6[PMo9V3O40] In acetonitrile for 2h; Reflux;A 11%
B 89%
N-(iminomethyl)-2-iodobenzamide

N-(iminomethyl)-2-iodobenzamide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With 8-quinolinol; sodium hydroxide; copper dichloride In water at 20℃; for 0.333333h; Reagent/catalyst; Microwave irradiation;90%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

anthranilic acid amide
28144-70-9

anthranilic acid amide

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

Conditions
ConditionsYield
With chloro-trimethyl-silane In acetonitrile at 70℃; for 24h;90%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

(7-azabenzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

(7-azabenzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)quinazoline
1003015-89-1

4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)quinazoline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1h;99%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

methyl 1-phenylprop-2-enyl carbonate
160879-62-9

methyl 1-phenylprop-2-enyl carbonate

3-((S)-1-phenylallyl)quinazolin-4(3H)-one

3-((S)-1-phenylallyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere; enantioselective reaction;99%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

diethyl 4-(sec-butyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 4-(sec-butyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

2-(1-Methylpropyl)-4(3H)-quinazolinone

2-(1-Methylpropyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
Stage #1: 4-Hydroxyquinazoline; diethyl 4-(sec-butyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 4h; Irradiation; Inert atmosphere; Sealed tube;
Stage #2: In 2,2,2-trifluoroethanol for 4h; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;
99%
Stage #1: 4-Hydroxyquinazoline; diethyl 4-(sec-butyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate With trifluoroacetic acid In 2,2,2-trifluoroethanol at 20℃; for 4h; Sealed tube; Irradiation; Inert atmosphere;
Stage #2: In 2,2,2-trifluoroethanol at 20℃; for 4h; Solvent; Reagent/catalyst; Wavelength;
97%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(4'-methylphenyl)-prop-2-enyl methyl carbonate

1-(4'-methylphenyl)-prop-2-enyl methyl carbonate

3-((S)-1-p-tolylallyl)quinazolin-4(3H)-one

3-((S)-1-p-tolylallyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;98%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(3'-bromophenyl)-prop-2-enyl methyl carbonate

1-(3'-bromophenyl)-prop-2-enyl methyl carbonate

3-((S)-1-(3-bromophenyl)allyl)quinazolin-4(3H)-one

3-((S)-1-(3-bromophenyl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;98%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(2'-naphthyl)-prop-2-enyl methyl carbonate

1-(2'-naphthyl)-prop-2-enyl methyl carbonate

3-((S)-1-(naphthalen-3-yl)allyl)quinazolin-4(3H)-one

3-((S)-1-(naphthalen-3-yl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;98%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

methyl 1-(thiophen-3-yl)allyl carbonate

methyl 1-(thiophen-3-yl)allyl carbonate

3-((S)-1-(thiophen-3-yl)allyl)quinazolin-4(3H)-one

3-((S)-1-(thiophen-3-yl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;98%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

diethyl 2,6-dimethyl-4-(pentan-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 2,6-dimethyl-4-(pentan-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

2-(pentan-3-yl)quinazolin-4(3H)-one

2-(pentan-3-yl)quinazolin-4(3H)-one

Conditions
ConditionsYield
Stage #1: 4-Hydroxyquinazoline; diethyl 2,6-dimethyl-4-(pentan-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate With trifluoroacetic acid In 2,2,2-trifluoroethanol at 20℃; for 4h; Sealed tube; Irradiation; Inert atmosphere;
Stage #2: In 2,2,2-trifluoroethanol at 20℃; for 4h;
98%
Stage #1: 4-Hydroxyquinazoline; diethyl 2,6-dimethyl-4-(pentan-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 4h; Irradiation; Inert atmosphere; Sealed tube;
Stage #2: In 2,2,2-trifluoroethanol for 4h; Irradiation; Inert atmosphere;
98%
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxygen; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 24h; Minisci Aromatic Substitution; Irradiation;89%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
1539-59-9

4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

2‐cyclohexylquinazolin‐4(3H)‐one
26059-80-3

2‐cyclohexylquinazolin‐4(3H)‐one

Conditions
ConditionsYield
Stage #1: 4-Hydroxyquinazoline; 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester With trifluoroacetic acid In 2,2,2-trifluoroethanol at 20℃; for 4h; Sealed tube; Irradiation; Inert atmosphere;
Stage #2: In 2,2,2-trifluoroethanol at 20℃; for 4h;
98%
Stage #1: 4-Hydroxyquinazoline; 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester With trifluoroacetic acid In 2,2,2-trifluoroethanol at 35℃; for 4h; Irradiation; Inert atmosphere; Sealed tube;
Stage #2: In 2,2,2-trifluoroethanol for 4h; Irradiation; Inert atmosphere;
98%
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxygen; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 24h; Minisci Aromatic Substitution; Irradiation;78%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

benzylamine
100-46-9

benzylamine

4-(benzylamino)quinazoline
100818-54-0

4-(benzylamino)quinazoline

Conditions
ConditionsYield
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane at 125℃; for 2h;97%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(4'-fluorophenyl)-prop-2-enyl methyl carbonate

1-(4'-fluorophenyl)-prop-2-enyl methyl carbonate

3-((S)-1-(4-fluorophenyl)allyl)quinazolin-4(3H)-one

3-((S)-1-(4-fluorophenyl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;97%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(4'-bromophenyl)-prop-2-enyl methyl carbonate
170938-18-8

1-(4'-bromophenyl)-prop-2-enyl methyl carbonate

3-((S)-1-(4-bromophenyl)allyl)quinazolin-4(3H)-one

3-((S)-1-(4-bromophenyl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;97%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(furan-3-yl)allyl methyl carbonate

1-(furan-3-yl)allyl methyl carbonate

3-((S)-1-(furan-3-yl)allyl)quinazolin-4(3H)-one

3-((S)-1-(furan-3-yl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;97%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

2-[4-oxo-3,4-dihydroquinazolin-3-yl]benzonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; Temperature;96.4%
With potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; Reagent/catalyst; Temperature;96.4%
With potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; Temperature;96.4%
With potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; Temperature;96.4%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

4-methoxy-phenol
150-76-5

4-methoxy-phenol

4-(4-methoxyphenoxy)quinazoline
93866-13-8

4-(4-methoxyphenoxy)quinazoline

Conditions
ConditionsYield
Stage #1: 4-Hydroxyquinazoline With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate In tetrahydrofuran at 20℃; for 0.833333h; Inert atmosphere;
Stage #2: 4-methoxy-phenol With caesium carbonate In tetrahydrofuran at 20℃; for 0.5h;
96%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20 - 60℃; for 52h;75%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

benzyl alcohol
100-51-6

benzyl alcohol

4-(benzyloxy)quinazoline
100880-35-1

4-(benzyloxy)quinazoline

Conditions
ConditionsYield
Stage #1: 4-Hydroxyquinazoline With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate In tetrahydrofuran at 20℃; for 0.833333h; Inert atmosphere;
Stage #2: benzyl alcohol With caesium carbonate at 20℃; for 1.16667h;
96%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

n-Octylamine
111-86-4

n-Octylamine

N-octylquinazolin-4-amine
22754-11-6

N-octylquinazolin-4-amine

Conditions
ConditionsYield
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane at 125℃; for 2h;96%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(2-chloroethyl)pyrrolidine hydrochloride
7250-67-1

1-(2-chloroethyl)pyrrolidine hydrochloride

3-[2-(pyrrolidin-1-yl)ethyl]-3,4-dihydroquinazoline-4-one

3-[2-(pyrrolidin-1-yl)ethyl]-3,4-dihydroquinazoline-4-one

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone for 24h; Reflux;96%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(2-haloethyl)pyrrolidine

1-(2-haloethyl)pyrrolidine

3-[2-(pyrrolidin-1-yl)ethyl]-3,4-dihydroquinazoline-4-one

3-[2-(pyrrolidin-1-yl)ethyl]-3,4-dihydroquinazoline-4-one

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone for 24h; Reflux;96%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

1-(4'-chlorophenyl)-prop-2-enyl methyl carbonate
496789-08-3

1-(4'-chlorophenyl)-prop-2-enyl methyl carbonate

3-((S)-1-(4-chlorophenyl)allyl)quinazolin-4(3H)-one

3-((S)-1-(4-chlorophenyl)allyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;96%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

(hex-1-en-3-yl)methyl carbonate
83135-00-6

(hex-1-en-3-yl)methyl carbonate

3-((R)-hex-1-en-3-yl)quinazolin-4(3H)-one

3-((R)-hex-1-en-3-yl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;96%
4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

6-(tert-butyldimethylsilyloxy)hex-1-en-3-yl methyl carbonate

6-(tert-butyldimethylsilyloxy)hex-1-en-3-yl methyl carbonate

3-((R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-yl)quinazolin-4(3H)-one

3-((R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-yl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-(+)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] In 1,2-dichloro-ethane at 80℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;96%

491-36-1Relevant articles and documents

Application of organolithium in organic synthesis: A simple and convenient procedure for the synthesis of more complex 6-substituted 3H-quinazolin-4-ones

El-Hiti, Gamal A.

, p. 323 - 331 (2004)

6-Methyl-3H-quinazolin-4-one reacted with alkyllithium reagents at -78°C in THF to give 2-alkyl-1,2-dihydro-6-methyl-3H-quinazolin-4-ones in high yields. However, no reaction took place when LDA was used as the lithium reagent. 6-Bromo-3H-quinazolin-4-one reacted with excessive butyllithium to give 2-butyl-1,2-dihydro-3H-quinazolin-4-ones in very good yields. However, the lithiation of 6-bromo-3H-quinazolin-4-one was achieved by the use of a combination of methyllithium (1.1 equivalents) and tert-butyllithium (2.2 equivalents) at -78°C in THF. The dilithio reagent thus obtained reacted with a variety of electrophiles (H2O, iodoethane, benzaldehyde, anisaldehyde, cyclohexanone, 2-hexanone, benzophenone, phenyl isothiocyanate, TITD) to give the corresponding 6-substituted 3H-quinazolin-4-ones in excellent yields. Reaction of the dilithio reagent with 1,3-dibromopropane gave 6,6′-(propanediyl)bis(3H-quinazolin-4-one). Springer-Verlag 2003.

Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

Kwon, Se Hyun,Seo, Hong-Ahn,Cheon, Cheol-Hong

, p. 5280 - 5283 (2016)

The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).

Synthesis and antifungal activities of N3-substituted quinazolin-4-one catalyzed by 3-Methylimidazole ionic liquids

Liu,Liu,Ji,Sun,Liu,Wen,Xu

, p. 9853 - 9856 (2013)

N3-Substituted quinazolin-4-one was synthesized by alkyl bromide and quinazolin-4-one was synthesized by anthranilic acid and formamide, catalyzing in various 3-methylimidazole ionic liquids and TBAB. The results showed that the yield of N3-substituted quinazolin-4-one increased appreciably and the reaction time shorted under ionic liquids and TBAB. Using 1-methyl-3-(2-hydroxyl-3- acetoxylpropyl)imidazolium fluoroborate or 1-propyl-3-methylimidazole fluoroborate as catalyst, the yield of N3-benzylquinazolin-4-one reached 85.1 and 82.0 %, increased 27 % more than the yield of traditional conditions. The compounds were evaluated for their in vitro antifungal activity against Fusarium graminearum, Fusarium oxysporum and Cytospora mandshurica. Compound 3f inhibited Fusarium graminearum with EC 50 28.85 μg/mL, Fusarium oxysporum with EC50 24.68 μg/mL and Cytospora mandshurica with EC50 37.67 μg/mL.

Di-4(3H)-quinazolinon-2-yl derivatives from the diacid chlorides of pinic and sym-homopinic acids

Avotin'sh,Petrova,Strakov

, p. 1241 - 1243 (2001)

The corresponding diamides have been synthesized by the interaction of the diacid chlorides of cis-2,2-dimethyl-3-carboxycyclobutaneacetic acid (pinic acid) and cis-2,2-dimethylcyclobutane-1,3-diacetic acid (sym-homopinic acid) with two equivalents of anthranilic acid. Treatment of the diamides with formamide gave 2,2-dimethyl-1-[4(3H)-quinazolinon-2-yl]methyl-3- [4(3H)-quinazolinon-2-yl]cyclobutane and 2,2-dimethyl-1,3-di[4(3H)-quinazolinon-2-ylmethyl]cyclobutane respectively.

2-(3-ethyl-2,2-dimethylcyclobutyl-methyl)-4(3H)-quinazolinones

Avotin'sh,Petrova,Pastors,Strakov

, p. 722 - 728 (1999)

Anthranilic acid and its 5-bromo and 4-chloro derivatives react with pinanoic and pinonoic acid chlorides to give the corresponding N-acyl derivatives. The pinanoyl derivatives give the corresponding 2-(3-ethyl-2,2-dimethyl-cyclobutylmethyl)-4-(3H)-quinazolinones when refluxed in formamide. Pinanoylanthranilic acid reacts with dicyclohexylcarbodiimide to give 2-(3-ethyl-2,2-dimethyl-cydobutylmethyl)benz-3,1-oxazin-4(H)-one and subsequently with hydrazine hydrate to give 3-amino-2-(3-ethyl-2,2-dimethylcyclobutylmethyl)-4(3H)-quinazolinone. Refluxing of the pinanoyl- and pinonoylanthranilic acids with acetic anhydride gives acetylanthranilic acid, and pinonoylanthranilic acid gives 4(3H)-quinazolinone with formamide. 1999 KluwerAcademic/Plenum Publishers.

Synthesis and biological activities of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety

Yan, Bo-Ren,Lv, Xin-Yang,Du, Huan,Gao, Man-Ni,Huang, Jian,Bao, Xiao-Ping

, p. 983 - 993 (2016)

A series of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety were synthesised and their antimicrobial activities were evaluated. All the target compounds were characterised by 1H NMR, 13C NMR, ESI-MS, IR and elemental analyses. The single crystal structure of 3-((5-((2-fluorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIi) was also determined. The preliminary bioassays indicated that some of the target compounds possessed good antimicrobial activities. For example, 3-((4-phenyl-5-((4-(trifluoromethyl)benzyl)thio)-4H- 1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIs) exhibited the best inhibitory effect against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri with the half-effective concentration (EC50) values of 47.6 μg mL-1 and 22.1 μg mL-1, respectively, which were superior to the commercial bactericide, bismerthiazol. Meanwhile, 3-((5-((4-chlorobenzyl)thio)-4-phenyl-4H- 1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one (VIIh) exhibited better fungicidal activities against Pellicularia sasakii and Colletotrichum capsici at the concentration of 50 μg mL-1, in comparison with the commercial fungicide, hymexazol.

A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)- ones

Wang, Bin,Li, Zeng,Wang, Xiao Ning,Tan, Jia Heng,Gu, Lian Quan,Huang, Zhi Shu

, p. 951 - 953 (2011)

A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)- ones and its derivatives using the condensation reaction of substituted 2-aminobenzamide and orthoesters is reported.

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

Dung, Do T. M.,Park, Eun J.,Anh, Duong T.,Hai, Pham-The,Huy, Le D.,Jun, Hye W.,Kwon, Joo-Hee,Young Ji,Kang, Jong S.,Tung, Truong T.,Dung, Phan T. P.,Han, Sang-Bae,Nam, Nguyen-Hai

, (2021/10/25)

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors

Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui

, p. 14895 - 14911 (2021/10/12)

The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong

, (2021/08/03)

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

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