Structural analogs of umifenovir 2*. The synthesis and antiHIV activity study of new regioisomeric (trans-2-phenylcyclopropyl)-1H-indole derivatives

被引:11
作者
Schols, Dominique [1 ]
Ruchko, Evsey A. [2 ]
Lavrenov, Sergey N. [3 ]
Kachala, Vadim V. [4 ]
Nawrozkij, Maksim B. [5 ]
Babushkin, Alexandre S. [5 ]
机构
[1] Rega Inst, B-3000 Louvain, Belgium
[2] Closed Joint Stock Co Farm Synth, Moscow 111024, Russia
[3] GF Gauze Sci Res Inst New Antibiot, Moscow 119021, Russia
[4] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[5] Volgograd State Tech Univ, 28 Lenina Ave, Volgograd 400005, Russia
基金
俄罗斯基础研究基金会;
关键词
umifenovir; conformationally restricted analogs; antiviral activity; REVERSE-TRANSCRIPTASE INHIBITORS; V OBLASTI KHINONOV; BIOLOGICAL EVALUATIONS; NENITZESCU REACTION; OXINDOLES; DESIGN; POTENT;
D O I
10.1007/s10593-016-1807-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report new carboanalogs of umifenovir - regioisomeric derivatives of ethyl 5-hydroxy-(trans-2-phenylcyclopropyl)-1De-indole-3-carboxylate. The inhibition of HIV replication by umifenovir and its carboanalogs at micromolar concentration range has been demonstrated for the first time.
引用
收藏
页码:978 / 983
页数:6
相关论文
共 19 条
[1]  
Allen Jr G. R., 1973, ORG REACTIONS, V20, P385
[2]   Structural Analogs of Umifenovir. 1. Synthesis and Biological Activity of Ethyl 5-Hydroxy-1-Methyl-2-(Trans-2-Phenylcyclopropyl)-1H-Indole-3-Carboxylate [J].
Balzarini, J. ;
Ruchko, E. A. ;
Zakharova, E. K. ;
Kameneva, I. Yu. ;
Nawrozkij, M. B. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (04) :489-495
[3]   ISOMERIC MANNICH BASES DERIVED FROM ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE [J].
BELL, MR ;
OESTERLI.R ;
BEYLER, AL ;
HARDING, HR ;
POTTS, GO .
JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (02) :264-&
[4]   Arbidol as a broad-spectrum antiviral: An update [J].
Blaising, Julie ;
Polyak, Stephen J. ;
Pecheur, Eve-Isabelle .
ANTIVIRAL RESEARCH, 2014, 107 :84-94
[5]  
GRINEV AN, 1962, ZH OBSHCH KHIM+, V32, P1948
[6]  
GRINEV AN, 1955, ZH OBSHCH KHIM+, V25, P1355
[7]  
Grinshtein V.Ya., 1963, IZV AKAD NAUK LATV K, V1, P106
[8]   Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2 [J].
Jiang, T ;
Kuhen, KL ;
Wolff, K ;
Yin, H ;
Bieza, K ;
Caldwell, J ;
Bursulaya, B ;
Tuntland, T ;
Zhang, KY ;
Karanewsky, D ;
He, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (08) :2109-2112
[9]  
Jiang T, 2006, BIOORG MED CHEM LETT, V16, P2105, DOI 10.1016/j.bmcl.2006.01.073
[10]   OBSERVATIONS ON MECHANISM OF NENITZESCU REACTION [J].
KUCKLANDER, U .
TETRAHEDRON, 1972, 28 (20) :5251-+