Synthesis and biological evaluation of new coumarins bearing 2,4-diaminothiazole-5-carbonyl moiety

被引：46

作者：

Ayati, Adileh ^{[1
]}

Bakhshaiesh, Tayebeh Oghabi ^{[2
]}

Moghimi, Setareh ^{[1
]}

Esmaeili, Rezvan ^{[2
]}

Majidzadeh-A, Keivan ^{[2
]}

Safavi, Maliheh ^{[3
]}

Firoozpour, Loghman ^{[1
]}

Emami, Saeed ^{[4
,5
]}

Foroumadi, Alireza ^{[1
,6
]}

机构：

[1] Univ Tehran Med Sci, Inst Pharmaceut Sci TIPS, Tehran, Iran

[2] ACECR, Motamed Canc Inst, Breast Canc Res Ctr, Dept Genet, Tehran, Iran

[3] Iranian Res Org Sci & Technol, Dept Biotechnol, POB 3353-5111, Tehran, Iran

[4] Mazandaran Univ Med Sci, Dept Med Chem, Fac Pharm, Sari, Iran

[5] Mazandaran Univ Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, Sari, Iran

[6] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran, Iran

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2018年 / 155卷

基金：

美国国家科学基金会;

关键词：

Anticancer; Antioxidant; Coumarin; Cytotoxic activity; Thiazole; CHROMENE-BASED CHALCONES; IN-VITRO CYTOTOXICITY; ANTICANCER AGENTS; ANTIOXIDANT ACTIVITY; ANTITUMOR EVALUATION; MEDICINAL CHEMISTRY; FACILE SYNTHESIS; DERIVATIVES; DISCOVERY; CANCER;

D O I：

10.1016/j.ejmech.2018.06.015

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of new coumarin-containing compounds 3a-1 and 4a-c was designed and synthesized based on the chalcone-type 4-amino-5-cinnamoylthiazole scaffold 2, and screened for their in vitro anticancer and antioxidant activities. Representatively, the 2-thiomorpholinothiazole derivative 3k with IC50 values of 7.5-16.9 mu g/ml demonstrated good cytotoxic effects against tested cell lines MCF-7, HepG2 and SW480. Further investigation by flow cytometric analysis confirmed that this compound induces apoptotic cell death in MCF-7 cells and cause G1-phase arrest in the cell cycle. Moreover, most of compounds had intrinsic potential for radical scavenging activity and ferric-reducing power as investigated by DPPH and FRAP assays. (C) 2018 Elsevier Masson SAS. All rights reserved.

引用

页码：483 / 491

页数：9

共 38 条

[1] Facile synthesis and antiproliferative activity of 7H-benzo[7,8] chromeno[2,3-d]pyrimidin-8-amines [J].

Akrami, Hamidreza ;

Safavi, Maliheh ;

Mirjalili, Bibi Fatemeh ;

Ashkezari, Mahmood Dehghani ;

Dadfar, Farhang ;

Mohaghegh, Najme ;

Emami, Saeed ;

Salehi, Fahimeh ;

Nadri, Hamid ;

Ardestani, Sussan K. ;

Firoozpour, Loghman ;

Khoobi, Mehdi ;

Foroumadi, Alireza .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 127 :128-136

[2] Novel coumarin derivatives bearing N-benzyl pyridinium moiety: Potent and dual binding site acetylcholinesterase inhibitors [J].

Alipour, Masoumeh ;

Khoobi, Mehdi ;

Foroumadi, Alireza ;

Nadri, Hamid ;

Moradi, Alireza ;

Sakhteman, Amirhossein ;

Ghandi, Mehdi ;

Shafiee, Abbas .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (24) :7214-7222

[3]

[Anonymous], 2017, MAJALLAH I DANISHGAH

[4] Induction of apoptosis through tubulin inhibition in human cancer cells by new chromene-based chalcones [J].

Aryapour, Hassan ;

Riazi, Gholam Hossein ;

Ahmadian, Shahin ;

Foroumadi, Alireza ;

Mahdavi, Majid ;

Emami, Saeed .

PHARMACEUTICAL BIOLOGY, 2012, 50 (12) :1551-1560

[5] Biological evaluation of synthetic analogues of curcumin: chloro-substituted-2′-hydroxychalcones as potential inhibitors of tubulin polymerization and cell proliferation [J].

Aryapour, Hassan ;

Riazi, Gholam Hossein ;

Foroumadi, Alireza ;

Ahmadian, Shahin ;

Shafiee, Abbas ;

Karima, Oveis ;

Mahdavi, Majid ;

Emami, Saeed ;

Sorkhi, Maedeh ;

Khodadady, Sirus .

MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (04) :503-510

[6] Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery [J].

Ayati, Adile ;

Emami, Saeed ;

Asadipour, Ali ;

Shafiee, Abbas ;

Foroumadi, Alireza .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :699-718

[7] Synthesis and biological evaluation of 4-amino-5-cinnamoylthiazoles as chalcone-like anticancer agents [J].

Ayati, Adileh ;

Esmaeili, Rezvan ;

Moghimi, Setareh ;

Bakhshaiesh, Tayebeh Oghabi ;

Eslami-S, Zahra ;

Majidzadeh-A, Keivan ;

Safavi, Maliheh ;

Emami, Saeed ;

Foroumadi, Alireza .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 145 :404-412

[8] 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents [J].

Azizmohammadi, Mohammad ;

Khoobi, Mehdi ;

Ramazani, Ali ;

Emami, Saeed ;

Zarrin, Abdolhossein ;

Firuzi, Omidreza ;

Miri, Ramin ;

Shafiee, Abbas .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 59 :15-22

[9]

Benzie IFF, 1999, METHOD ENZYMOL, V299, P15

[10] Synthesis and antitumor evaluation of novel sulfonylcycloureas derived from nitrogen mustard [J].

Cheloufi, H. ;

Belhani, B. ;

Ouk, T. S. ;

Zerrouki, R. ;

Aouf, N. -E. ;

Berredjem, M. .

MOLECULAR DIVERSITY, 2016, 20 (02) :399-405

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