Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4) thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

被引：43

作者：

Tiwari, Shailee V. ^{[1
]}

Seijas, Julio A. ^{[2
]}

Pilar Vazquez-Tato, M. ^{[2
]}

Sarkate, Aniket P. ^{[3
]}

Lokwani, Deepak K. ^{[3
]}

Nikalje, Anna Pratima G. ^{[1
]}

机构：

[1] YB Chavan Coll Pharm, Dr Rafiq Zakaria Campus, Aurangabad 431001, Maharashtra, India

[2] Univ Santiago de Compostela, Fac Ciencias, Dept Quim Organ, Lugo 27002, Spain

[3] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem Technol, Aurangabad 431004, Maharashtra, India

来源：

MOLECULES | 2016年 / 21卷 / 08期

关键词：

1,3,4-thiadiazolo(3,2-alpha)pyrimidine; ultrasound-promoted synthesis; ADME; docking; MESOIONIC PURINONE ANALOGS; DHFR INHIBITORS SYNTHESIS; ANTIPROLIFERATIVE ACTIVITY; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY;

D O I：

10.3390/molecules21080894

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Herein, we report an environmentally friendly, rapid, and convenient one-pot ultrasound-promoted synthesis of 5-amino-2-(4-chlorophenyl)-7-substituted phenyl-8,8a-dihydro-7H-(1,3,4) thiadiazolo(3,2-alpha)pyrimidine-6-carbonitrile derivatives. The in-vitro anticancer activities of these compounds were evaluated against four human tumor cell lines. Among all the synthesized derivatives, compound 4i, which has substituent 3-hydroxy-4-methoxyphenyl is found to have the highest GI(50) value of 32.7 mu M, 55.3 mu M, 34.3 mu M, 28.9 mu M for MCF-7, K562, HeLa and PC-3 cancer cell lines respectively. A docking study of the newly synthesized compounds were performed, and the results showed good binding mode in the active site of thymidylate synthase enzyme. ADME properties of synthesized compounds were also studied and showed good drug like properties.

引用

页数：13

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