Synthesis, molecular modeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole-2(3H)-thione quinolone derivatives as novel anticancer agent

被引：101

作者：

Sun, Juan ^{[1
]}

Zhu, Hui ^{[1
]}

Yang, Zhong-Ming ^{[1
]}

Zhu, Hai-Liang ^{[1
]}

机构：

[1] Shandong Univ Technol, Sch Life Sci, Zibo 255049, Shandong, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 60卷

关键词：

Quinoline; 1,3,4-Oxadiazole; Antiproliferative; Telomerase inhibitor; Molecular docking; ANTITUMOR; 1,4-BENZODIOXAN; DOCKING; DESIGN; MOIETY;

D O I：

10.1016/j.ejmech.2012.11.039

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of quinoline derivatives (4a-4o) have been synthesized and their biological activities were also evaluated as potential telomerase inhibitors. Bioassay tests demonstrated that most of the compounds exhibited substantial broad-spectrum antitumor activity against the three cancer cell lines (HepG2, SGC-7901 and MCF-7). Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. Compounds 4d and 4i displayed the most potent anticancer activities, which were comparable to the positive control. Docking simulation was performed to position compounds 4d and 4i into the telomerase structure active site to determine the probable binding model. Compounds 4d and 4i with potent inhibitory activity in tumor growth inhibition may be potential anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：23 / 28

页数：6

共 28 条

[11] Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines.: Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3 [J].

Hranjec, Marijana ;

Kralj, Marijeta ;

Piantanida, Ivo ;

Sedic, Mirela ;

Suman, Lidija ;

Pavelic, Kresimir ;

Karminski-Zamola, Grace .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (23) :5696-5711

[12] Synthesis of new dihydroindeno[1,2-c]isoquinoline and indenoisoquinolinium chloride topoisomerase I inhibitors having high in vivo anticancer activity in the hollow fiber animal model [J].

Jayaraman, M ;

Fox, BM ;

Hollingshead, M ;

Kohlhagen, G ;

Pommier, Y ;

Cushman, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (01) :242-249

[13] Synthesis and biological evaluation of novel 1β-methylcarbapenems having a new moiety at C-2 [J].

Kang, YK ;

Shin, KJ ;

Yoo, KH ;

Seo, KJ ;

Park, SY ;

Kim, DJ ;

Park, SW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2385-2390

[14] Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues [J].

Khan, MTH ;

Choudhary, MI ;

Khan, KM ;

Rani, M ;

Atta-ur-Rahman .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (10) :3385-3395

[15]

Ko DH, 1997, MED CHEM RES, V7, P313

[16] Excellent Outcomes With Adjuvant Toremifene or Tamoxifen in Early Stage Breast Cancer [J].

Lewis, Jaime D. ;

Chagpar, Anees B. ;

Shaughnessy, Elizabeth A. ;

Nurko, Jacob ;

McMasters, Kelly ;

Edwards, Michael J. .

CANCER, 2010, 116 (10) :2307-2315

[17]

Loetchutinat C, 2003, CHEM PHARM BULL, V51, P728

[18] Discovery of a new insecticide lead by optimizing a target-diverse scaffold: Tetrazolinone derivatives [J].

Luo, Yan-Ping ;

Yang, Guang-Fu .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) :1716-1724

[19] Adjuvant Targeted Therapy in Early Breast Cancer [J].

Mackey, John ;

McLeod, Deanna ;

Ragaz, Joseph ;

Gelmon, Karen ;

Verma, Sunil ;

Pritchard, Kathleen ;

Laing, Kara ;

Provencher, Louise ;

Charbonneau, Lauren F. .

CANCER, 2009, 115 (06) :1154-1168

[20]

Mishra A., 1998, ORIENT J CHEM, V14, P151

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