Pyrazoles, isoxazoles, and 1,2,3-triazoles as analogs of the natural cytostatic combretastatin A-4: efficient routes of synthesis, tubulin inhibition, and cytotoxicity

被引:1
作者
Kostin, Roman K. [1 ]
Marshavin, Aleksander S. [2 ]
机构
[1] IM Sechenov First Moscow State Med Univ, Sechenov Univ, Minist Hlth Russian Federat, 8,Bldg 2 Trubetskaya St, Moscow 119991, Russia
[2] Lomonosov Moscow State Univ, 1,Bldg 3 Leninskie Gory, Moscow 119991, Russia
关键词
combretastatin A-4; combretastatin analogs; 3,5-diarylisoxazole; heterocycles; pyrazole; pyrazoline; 1,2,3-triazole; tubulin; cytotoxicity; tubulin-binding agents; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY; POLYMERIZATION INHIBITORS; STRUCTURAL BASIS; COLCHICINE SITE; POTENT; DERIVATIVES; BINDING; DESIGN; AGENTS;
D O I
10.1007/s10593-021-03025-y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The review discusses the advantages and disadvantages of combretastatin A-4, presents the most effective methods for the synthesis of its 1,2,3-triazole, pyrazole, isoxazole analogs. The structural formulas of the analogs of combretastatin A-4 which are the most active against cancer cells, together with indicators of cytotoxicity, are also presented.
引用
收藏
页码:1061 / 1072
页数:12
相关论文
共 72 条
[1]   High-Resolution Microtubule Structures Reveal the Structural Transitions in αβ-Tubulin upon GTP Hydrolysis [J].
Alushin, Gregory M. ;
Lander, Gabriel C. ;
Kellogg, Elizabeth H. ;
Zhang, Rui ;
Baker, David ;
Nogales, Eva .
CELL, 2014, 157 (05) :1117-1129
[2]   Design, synthesis, cytotoxic evaluation and tubulin inhibitory activity of 4-aryl-5-(3,4,5-trimethoxyphenyl)-2-alkylthio-1H-imidazole derivatives [J].
Assadieskandar, Amir ;
Amini, Mohsen ;
Ostad, Seyed Nasser ;
Riazi, Gholam Hossein ;
Cheraghi-Shavi, Tayebe ;
Shafiei, Bentolhoda ;
Shafiee, Abbas .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (10) :2703-2709
[3]   Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin [J].
Bellina, Fabio ;
Cauteruccio, Silvia ;
Monti, Susanna ;
Rossi, Renzo .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (22) :5757-5762
[4]   Montmorillonite clay Cu(II) catalyzed domino one-pot multicomponent synthesis of 3,5-disubstituted isoxazoles [J].
Bharate, Sandip B. ;
Padala, Anil K. ;
Dar, Bashir A. ;
Yadav, Rammohan R. ;
Singh, Baldev ;
Vishwakarma, Ram A. .
TETRAHEDRON LETTERS, 2013, 54 (27) :3558-3561
[5]   Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin [J].
Bhattacharyya, Bhabatarak ;
Panda, Dulal ;
Gupta, Suvroma ;
Banerjee, Mithu .
MEDICINAL RESEARCH REVIEWS, 2008, 28 (01) :155-183
[6]   1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].
Bozorov, Khurshed ;
Zhao, Jiangyu ;
Aisa, Haji A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531
[7]   Development of combretastatins as potent tubulin polymerization inhibitors [J].
Bukhari, Syed Nasir Abbas ;
Kumar, Gajjela Bharath ;
Revankar, Hrishikesh Mohan ;
Qin, Hua-Li .
BIOORGANIC CHEMISTRY, 2017, 72 :130-147
[8]   Recent advances in microtubule-stabilizing agents [J].
Cao, Ya-Nan ;
Zheng, Ling -Li ;
Wang, Dan ;
Liang, Xiao-Xia ;
Gao, Feng ;
Zhou, Xian-Li .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :806-828
[9]   Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes [J].
Chalyk, Bohdan A. ;
Hrebeniuk, Kateryna V. ;
Fil, Yulia V. ;
Gavrilenko, Konstantin S. ;
Rozhenko, Alexander B. ;
Vashchenko, Bohdan V. ;
Borysov, Oleksandr V. ;
Biitseva, Angelina V. ;
Lebed, Pavlo S. ;
Bakanovych, Iulia ;
Moroz, Yurii S. ;
Grygorenko, Oleksandr O. .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24) :15877-15899
[10]   Combretastatin a-4 analogs as anticancer agents [J].
Chaudhary, Anurag ;
Pandeya, S. N. ;
Kumar, P. ;
Sharma, Py. ;
Gupta, S. ;
Soni, N. ;
Verma, K. K. ;
Bhardwaj, G. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (12) :1186-1205