Synthesis and antitumor evaluation of trimethoxyanilides based on 4(3H)-quinazolinone scaffolds

被引：91
作者：
Mohamed, Menshawy A. [1 ,2 ]
Ayyad, Rezk R. [3 ]
Shawer, Taghreed Z. [3 ]
Abdel-Aziz, Alaa A. -M. [4 ,5 ]
El-Azab, Adel S. [1 ,4 ]
机构：
[1] Al Azhar Univ, Fac Pharm, Dept Organ Chem, Cairo, Egypt
[2] Salman Bin Abdulaziz Univ, Coll Pharm, Dept Pharmaceut Chem, Alkharj, Saudi Arabia
[3] Al Azhar Univ, Fac Pharm, Dept Pharmaceut Chem, Cairo, Egypt
[4] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[5] Univ Mansoura, Fac Pharm, Dept Med Chem, Mansoura, Egypt
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2016年 / 112卷
关键词：
Quinazoline scaffolds; Synthesis; Anticancer; Broad spectrum; NCI; BIOLOGICAL EVALUATION; IN-VITRO; ANTICONVULSANT EVALUATION; SUBSTITUTED QUINAZOLINES; LUNG-CANCER; DESIGN; DERIVATIVES; INHIBITOR; ANALOGS; LAPATINIB;
D O I：
10.1016/j.ejmech.2016.02.002
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A novel series of 2-[(3-substituted-4(3H)-quinazolin-2-yl)thiol-N-(3,4,5-trimethoxyphenyl)acetamide (15-21) and 3-[(3-substituted-4(3H)-quinazolin-2-yl)thio]-N-(3,4,5-trimethoxyphenyl)propanamide (23-29) were designed, prepared and estimated for their anticancer activity in a solo dose 10 mu M of the test compounds in the NCI 57 cell lines panel assay. Compounds 20, 23, 26, 27 and 28 revealed extensive spectrum antitumor efficiency to numerous cell lines that belong to various tumor subpanels, while compounds 15, 16 and 19 possessed perceptive activity toward A498 and UO-31 renal cancer cell lines, and compound 17 showed selective effectiveness against NSC lung cancer NCI-H522 cell line. Additionally, compound 18 showed advanced activity against SR leukemia cell line, NSC lung cancer HOP-92 and renal cancer UO-31 cell lines. (C) 2016 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：106 / 113
页数：8
相关论文
共 42 条
[1]  
Abdel-Aziz A.A.-M., 2015, J ENZYM INHIB, P1
[2]   Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs [J].
Al-Obaid, Abdulrahman M. ;
Abdel-Hamide, Sami G. ;
El-Kashef, Hassan A. ;
Abdel-Aziz, Alaa A. -M. ;
El-Azab, Adel S. ;
Al-Khamees, Hamad A. ;
El-Subbagh, Hussein I. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (06) :2379-2391
[3]  
Al-Omar M., 2006, SYNTHESIS SOME NEW 4
[4]   Non-classical antifolates. Part 2: Synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones [J].
Al-Omary, Fatmah A. M. ;
Abou-zeid, Laila A. ;
Nagi, Mahmoud N. ;
Habib, El-Sayed E. ;
Abdel-Aziz, Alaa A-M. ;
El-Azab, Adel S. ;
Abdel-Hamide, Sami G. ;
Al-Omar, Mohamed A. ;
Al-Obaid, Abdulrahman M. ;
El-Subbagh, Hussein I. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (08) :2849-2863
[5]   Synthesis, anticonvulsant activity and molecular modeling study of some new hydrazinecarbothioamide, benzenesulfonohydrazide, and phenacylacetohydrazide analogues of 4(3H)-quinazolinone [J].
Al-Salem, Huda S. A. ;
Hegazy, Gehan H. ;
El-Taher, Kamal E. H. ;
El-Messery, Shahenda M. ;
Al-Obaid, Abdulrahman M. ;
El-Subbagh, Hussein I. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (07) :1490-1499
[6]  
Al-Suwaidan I.A., 2014, J ENZYM INHIB, P1
[7]  
Al-Suwaidan I.A., 2015, J ENZYM INHIB, P1
[8]   Design, synthesis and biological evaluation of 2-mercapto-3-phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study [J].
Al-Suwaidan, Ibrahim A. ;
Alanazi, Amer M. ;
Abdel-Aziz, Alaa A. -M. ;
Mohamed, Menshawy A. ;
El-Azab, Adel S. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (13) :3935-3941
[9]   Synthesis, analgesic and anti-inflammatory evaluation of some new 3H-quinazolin-4-one derivatives [J].
Alafeefy, Ahmed M. ;
Kadi, Adnan A. ;
El-Azab, Adel S. ;
Abdel-Hamide, Sami G. ;
Daba, Mohamad-Hesham Y. .
ARCHIV DER PHARMAZIE, 2008, 341 (06) :377-385
[10]   Synthesis of some new substituted iodoquinazoline derivatives and their antimicrobial screening [J].
Alafeefy, Ahmed M. ;
El-Azab, Adel S. ;
Mohamed, Menshawy A. ;
Bakhat, Mohamed Afroz ;
Abdel-Hamid, S. G. .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2011, 15 (04) :319-325
12345