Synthesis and antiproliferative activity of RITA and its analogs

被引：14

作者：

Jiang, Jianhua ^{[1
,2
]}

Ding, Chao ^{[1
,2
]}

Li, Lulu ^{[3
]}

Gao, Chunmei ^{[2
]}

Jiang, Yuyang ^{[2
,4
]}

Tan, Chunyan ^{[2
]}

Hua, Ruimao ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China

[2] Tsinghua Univ, Grad Sch Shenzhen, State Key Lab Shenzhen Key Lab Chem Biol, Minist Prov Jointly Constructed Base, Shenzhen 518055, Peoples R China

[3] Shenzhen Kivita Innovat Drug Discovery Inst, Shenzhen 518055, Peoples R China

[4] Tsinghua Univ, Sch Med, Dept Pharmacol & Pharmaceut Sci, Beijing 100084, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 49期

基金：

中国国家自然科学基金;

关键词：

Antiproliferative activity; 1,3-Butadiynes; Cyclocondensation; Heterocyclic triads; RITA; SMALL-MOLECULE RITA; CARCINOMA CELL-LINES; CATALYZED CYCLOADDITION; EFFICIENT SYNTHESIS; CANCER; 1,3-BUTADIYNES; DERIVATIVES; INHIBITORS; MDM2; P53;

D O I：

10.1016/j.tetlet.2014.10.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of RITA and a variety of five-membered heterocyclic triads by the cyclocondensation of 1,4-bis(5-substituted-2-thienyl or 2-furyl)-1,3-butadiynes with water or Na2S center dot 9H(2)O in the presence of KOH in DMSO is described. The study on the antiproliferative activities against K562, MCF-7, A549, and HCT116 tumor cells has revealed that some of the heterocyclic triads show higher antiproliferative activities than RITA, depending on the structures of substituents, the property of heteroatoms as well as their numbers. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6635 / 6638

页数：4

共 28 条

[1] Antiproliferative potential of sarcophine and its semisynthetic sulfur-containing derivatives against human mammary carcinoma cell lines [J].

Arif, Jamal M. ;

Sawant, Swapnali S. ;

El Sayed, Khalid A. ;

Kunhi, Muhammad ;

Subramanian, Manogaran P. ;

Siddiqui, Yunus M. ;

Youssef, Diaa T. A. ;

Al-Hussain, Khalid ;

Al-Ahdal, Mohammed N. ;

Al-Khodairy, Fahad .

JOURNAL OF NATURAL MEDICINES, 2007, 61 (02) :154-158

[2] Potassium Hydroxide/Dimethyl Sulfoxide Promoted Intramolecular Cyclization for the Synthesis of Benzimidazol-2-ones [J].

Beyer, Astrid ;

Reucher, Christine M. M. ;

Bolm, Carsten .

ORGANIC LETTERS, 2011, 13 (11) :2876-2879

[3]

Bilik P, 2001, CHEMBIOCHEM, V2, P559, DOI 10.1002/1439-7633(20010803)2:7/8<559::AID-CBIC559>3.0.CO

[4]

2-U

[5] Transition-Metal-Free O-, S-, and N-Arylation of Alcohols, Thiols, Amides, Amines, and Related Heterocycles [J].

Cano, Rafael ;

Ramon, Diego J. ;

Yus, Miguel .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) :654-660

[6] Targeting MDM2 by the small molecule RITA: towards the development of new multi-target drugs against cancer [J].

Espinoza-Fonseca, L. Michel .

THEORETICAL BIOLOGY AND MEDICAL MODELLING, 2005, 2

[7] Mdm2 promotes the rapid degradation of p53 [J].

Haupt, Y ;

Maya, R ;

Kazaz, A ;

Oren, M .

NATURE, 1997, 387 (6630) :296-299

[8] Small molecule RITA binds to p53, blocks p53-HDM-2 interaction and activates p53 function in tumors [J].

Issaeva, N ;

Bozko, P ;

Enge, M ;

Protopopova, M ;

Verhoef, LGGC ;

Masucci, M ;

Pramanik, A ;

Selivanova, G .

NATURE MEDICINE, 2004, 10 (12) :1321-1328

[9] Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: Structure-activity relationships of novel thiohydrazone analogues [J].

Kalinowski, Danuta S. ;

Sharpe, Philip C. ;

Bernhardt, Paul V. ;

Richardson, Des R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (24) :6212-6225

[10] Efficient synthesis of RITA and its analogues: derivation of analogues with improved antiproliferative activity via modulation of p53/miR-34a pathway [J].

Lin, Jinshun ;

Jin, Xiuli ;

Bu, Yiwen ;

Cao, Deliang ;

Zhang, Nannan ;

Li, Shangfu ;

Sun, Qinsheng ;

Tan, Chunyan ;

Gao, Chunmei ;

Jiang, Yuyang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (48) :9734-9746

← 1 2 3 →