Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis-Reference-Cited by-同舟云学术

Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis

Published:2020-01-16 Issue:2 Volume:70 Page:161-178
ISSN:1846-9558
Container-title:Acta Pharmaceutica
language:en
Short-container-title:

Author:

El-Badry Yaser A.¹²,El-Hashash Mahr A.³,Al-Ali Khalil⁴

Affiliation:

1. Organic Chemistry Laboratory , Faculty of Specific Education , Ain Shams University , Abbasseya 11566 , Cairo , Egypt

2. Organic Chemistry Department, Faculty of Science , Taif University , Khurma 21985 Kingdom of Saudi Arabia

3. Organic Chemistry Department Faculty of Science , Ain Shams University , Abbasseya 11566 Cairo , Egypt

4. Medical Laboratory Technology , Department, College of Applied Medical Sciences , Taibah University , Madinah 30001 Kingdom of Saudi Arabia

Abstract

Abstract A series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazo-line-4-one (2). The reinvestigation of the key starting quinazolinone 2 was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out N-alkylation and condensation reactions of compound 2 as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. In vitro antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4H)-yl)methyl]benzoate (3c), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3H)-one (3e), N’-[(E)-(2H-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10a), N’-[(E)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4H) -yl)acetohydrazide (10b) and N’-[(E)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10c).

Publisher

Walter de Gruyter GmbH

Subject

Pharmaceutical Science,Pharmacology,General Medicine

Link

https://www.sciendo.com/pdf/10.2478/acph-2020-0001

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