Stereoselective synthesis of 3,3-diarylacrylonitriles as tubulin polymerization inhibitors

被引：19

作者：

Fang, Zhenglai ^{[1
,2
]}

Song, Yunlong ^{[1
,2
]}

Sarkar, Taradas ^{[3
]}

Hamel, Ernest ^{[3
]}

Fogler, William E. ^{[4
]}

Agoston, Gregory E. ^{[4
]}

Fanwick, Phillip E. ^{[5
]}

Cushman, Mark ^{[1
,2
]}

机构：

[1] Purdue Univ, Sch Pharm & Pharmaceut Sci, Dept Med Chem & Mol Pharmacol, W Lafayette, IN 47907 USA

[2] Purdue Univ, Purdue Canc Ctr, W Lafayette, IN 47907 USA

[3] Natl Inst Hlth, Natl Canc Inst, Div Canc Treatment & Diag, Dev Therapeut Program,Toxicol & Pharmacol Branch, Frederick, MD 21702 USA

[4] EntreMed Inc, Rockville, MD 20850 USA

[5] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 11期

关键词：

D O I：

10.1021/jo800428b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 3,3-diarylacrylonitriles were synthesized stercoselectively as tubulin polymerization inhibitors for potential use in cancer chemotherapy. This synthetic route features stannylcupration and palladium-catalyzed Stille cross-coupling chemistry, allowing both E and Z isomers of 3,3-diarylacrylonitriles to be prepared in a very short sequence of reactions.

引用

页码：4241 / 4244

页数：4

共 50 条

[21] Arylthioindoles, potent inhibitors of tubulin polymerization
De Martino, G
La Regina, G
Coluccia, A
Edler, MC
Barbera, MC
Brancale, A
Wilcox, E
Hamel, E
Artico, M
Silvestri, R
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) : 6120 - 6123
[22] In silico Search for Tubulin Polymerization Inhibitors
Sahakyan, H. K.
Arakelov, G. G.
Nazaryan, K. B.
MOLECULAR BIOLOGY, 2018, 52 (04) : 604 - 608
[23] Celogentin mimetics as inhibitors of tubulin polymerization
Thombare, Varsha J.
Holden, James A.
Reynolds, Eric C.
O'Brien-Simpson, Neil M.
Hutton, Craig A.
JOURNAL OF PEPTIDE SCIENCE, 2020, 26 (03)
[24] Synthesis, biological evaluation, and molecular docking investigation of 3-amidoindoles as potent tubulin polymerization inhibitors
Chen, Peng
Zhuang, Yu-Xin
Diao, Peng-Cheng
Yang, Fang
Wu, Shao-Yu
Lv, Lin
You, Wen-Wei
Zhao, Pei-Liang
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 162 : 525 - 533
[25] Synthesis of Some New Indole-1,3,4-Oxadiazole Hybrids as Tubulin Polymerization Inhibitors
Boda, Sunitha
Nukala, Satheesh Kumar
Manchal, Ravinder
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2022, 48 (SUPPL 1) : S136 - S143
[26] Synthesis of Some New Indole-1,3,4-Oxadiazole Hybrids as Tubulin Polymerization Inhibitors
Satheesh Kumar Sunitha Boda
Ravinder Nukala
Russian Journal of Bioorganic Chemistry, 2022, 48 : S136 - S143
[27] Synthesis of C5-tethered indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors
Guggilapu, Sravanthi Devi
Lalita, Guntuku
Reddy, T. Srinivasa
Prajapti, Santosh Kumar
Nagarsenkar, Atulya
Ramu, Shymala
Brahma, Uma Rani
Lakshmi, Uppa Jaya
Vegi, Ganga Modi Naidu
Bhargava, Suresh K.
Babu, Bathini Nagendra
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 128 : 1 - 12
[28] 2-Anilino-3-Aroylquinolines as Potent Tubulin Polymerization Inhibitors
Srikanth, P. S.
Nayak, V. Lakshma
Babu, Korrapati Suresh
Kumar, G. Bharath
Ravikumar, A.
Kamal, Ahmed
CHEMMEDCHEM, 2016, 11 (18) : 2050 - 2062
[29] Synthesis and biological evaluation of curcumin inspired indole analogues as tubulin polymerization inhibitors
Ramya, P. V. Sri
Angapelly, Srinivas
Guntuku, Lalita
Digwal, Chander Singh
Babu, Bathini Nagendra
Naidu, V. G. M.
Kamal, Ahmed
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 127 : 100 - 114
[30] Synthesis of substituted biphenyl methylene indolinones as apoptosis inducers and tubulin polymerization inhibitors
Donthiboina, Kavitha
Anchi, Pratibha
Ramya, P. V. Sri
Karri, Shailaja
Srinivasulu, Gannoju
Godugu, Chandraiah
Shankaraiah, Nagula
Kamal, Ahmed
BIOORGANIC CHEMISTRY, 2019, 86 : 210 - 223

← 1 2 3 4 5 →