Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents

被引：117

作者：

Amin, Kamilia M. ^{[1
]}

Eissa, Amal A. M. ^{[1
]}

Abou-Seri, Sahar M. ^{[1
]}

Awadallah, Fadi M. ^{[1
]}

Hassan, Ghaneya S. ^{[1
]}

机构：

[1] Cairo Univ, Fac Pharm, Dept Pharmaceut Chem, Cairo, Egypt

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 60卷

关键词：

Coumarins; Pyrazoline; Phenylsulfonyl derivatives; Antitumor activity; BEARING BENZENE SULFONAMIDE; IN-VITRO; 4,5-DIHYDROPYRAZOLE DERIVATIVES; ANTICANCER; DISCOVERY; DESIGN; OPTIMIZATION; CYTOTOXICITY; CHEMOTHERAPY; INHIBITORS;

D O I：

10.1016/j.ejmech.2012.12.004

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two groups of coumarin pyrazoline hybrids were synthesized. The target compounds were obtained by cyclization of the coumarin chalcones with various substituted hydrazines to produce the corresponding pyrazolines through 1,4-addition on alpha,beta-unsaturated carbonyl system. Selected compounds were investigated for their anticancer activity toward 60 cancer cell lines according to US NCI protocol where breast cancer MCF7 and colon cancer HCT-116 were the most susceptible to the influence of compounds 7d, 8c and 9c. Encouraged by this, all final compounds were screened against colorectal cell line HCT-116. The tested compounds exhibited high potency with IC50 ranging from 0.01 mu M to 2.8 mu M. Moreover, compound 9c which possessed the highest cytotoxicity proved to have weak enzyme inhibitory activity against PI3K (p110 alpha/p85 alpha). (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：187 / 198

页数：12

共 54 条

[1] ANTICANCER SPECIFICITY OF SOME ELLIPTICINIUM SALTS AGAINST HUMAN BRAIN-TUMORS IN-VITRO [J].

ACTON, EM ;

NARAYANAN, VL ;

RISBOOD, PA ;

SHOEMAKER, RH ;

VISTICA, DT ;

BOYD, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (14) :2185-2189

[2]

AHLUWALIA VK, 1988, INDIAN J CHEM B, V27, P70

[3]

Alfonso M., 2010, BIOORG MED CHEM LETT, V20, P7255

[4] Design, synthesis and vasorelaxant evaluation of novel coumarin-pyrimidine hybrids [J].

Amin, Kamilia M. ;

Awadalla, Fadi M. ;

Eissa, Amal A. M. ;

Abou-Seri, Sahar M. ;

Hassan, Ghaneya S. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (20) :6087-6097

[5]

[Anonymous], 2012, CANC TRENDS PROGR RE

[6] Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents [J].

Bano, Sameena ;

Javed, Kalim ;

Ahmad, Shamim ;

Rathish, I. G. ;

Singh, Surender ;

Alam, M. S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :5763-5768

[7] ALLERGENIC ALPHA-METHYLENE-GAMMA-BUTYROLACTONES - BETA-HYDROXY-ALPHA-METHYLENE-GAMMA-BUTYROLACTONES .2. SYNTHESES FROM ETHYL 2-(PHENYLTHIO)PROPIONATE AND ALPHA-ACETOXY ALDEHYDES [J].

BARBIER, P ;

BENEZRA, C .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (16) :2705-2709

[8] Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents [J].

Bashir, Rafia ;

Ovais, Syed ;

Yaseen, Shafiya ;

Hamid, Hinna ;

Alam, M. S. ;

Samim, Mohammad ;

Singh, Surender ;

Javed, Kalim .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (14) :4301-4305

[9] Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents [J].

Belluti, Federica ;

Fontana, Gabriele ;

Dal Bo, Laura ;

Carenini, Nives ;

Giommarelli, Chiara ;

Zunino, Franco .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (10) :3543-3550

[10] A selective inhibitor of the p110δ isoform of PI 3-kinase inhibits AML cell proliferation and survival and increases the cytotoxic effects of VP16 [J].

Billottet, C. ;

Grandage, V. L. ;

Gale, R. E. ;

Quattropani, A. ;

Rommel, C. ;

Vanhaesebroeck, B. ;

Khwaja, A. .

ONCOGENE, 2006, 25 (50) :6648-6659

← 1 2 3 4 5 6 →