Conformational preferences of non-nucleoside HIV-1 reverse transcriptase inhibitors

被引：89

作者：

Parreira, RLT ^{[1
]}

Abrahao, O ^{[1
]}

Galembeck, SE ^{[1
]}

机构：

[1] Univ Sao Paulo, Lab Modelagem Mol, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto, BR-14040901 Ribeirao Preto, SP, Brazil

来源：

TETRAHEDRON | 2001年 / 57卷 / 16期

基金：

巴西圣保罗研究基金会;

关键词：

AIDS; intramolecular interactions; hydrogen bonds; pi-interactions; natural bond orbital analysis;

D O I：

10.1016/S0040-4020(01)00193-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTI) are a class of compounds that present a common butterfly-like conformation. In the present study, the intramolecular factors that contribute to this conformation were studied. Hydrogen bonds have been analysed by geometric and electrostatic criteria. Only the former allow the elucidation of the relative intensity of hydrogen bonds. The interaction between aromatic rings may contribute to the preferential conformation. For some other NNRTI, it is not possible to explain the butterfly-like conformation on the basis of hydrogen bond and aromatic interactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3243 / 3253

页数：11

相关论文

共 64 条

[51] THE STRUCTURE OF HIV-1 REVERSE-TRANSCRIPTASE COMPLEXED WITH 9-CHLORO-TIBO - LESSONS FOR INHIBITOR DESIGN [J].

REN, JS ;

ESNOUF, R ;

HOPKINS, A ;

ROSS, C ;

JONES, Y ;

STAMMERS, D ;

STUART, D .

STRUCTURE, 1995, 3 (09) :915-926

[52] BIS(HETEROARYL)PIPERAZINE (BHAP) REVERSE-TRANSCRIPTASE INHIBITORS - STRUCTURE-ACTIVITY-RELATIONSHIPS OF NOVEL SUBSTITUTED INDOLE ANALOGS AND THE IDENTIFICATION OF 1-[(5-METHANESULFONAMIDO-1H-INDOL-2-YL)-CARBONYL]-4-[3-[(1-METHYLETHYL)AMINO]-PYRIDINYL]PIPERAZINE MONOMETHANESULFONATE (U-90152S), A 2ND-GENERATION CLINICAL CANDIDATE [J].

ROMERO, DL ;

MORGE, RA ;

GENIN, MJ ;

BILES, C ;

BUSSO, M ;

RESNICK, L ;

ALTHAUS, IW ;

REUSSER, F ;

THOMAS, RC ;

TARPLEY, WG .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (10) :1505-1508

[53] 2-PYRIDINONE DERIVATIVES - A NEW CLASS OF NONNUCLEOSIDE, HIV-1-SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS [J].

SAARI, WS ;

HOFFMAN, JM ;

WAI, JS ;

FISHER, TE ;

ROONEY, CS ;

SMITH, AM ;

THOMAS, CM ;

GOLDMAN, ME ;

OBRIEN, JA ;

NUNBERG, JH ;

QUINTERO, JC ;

SCHLEIF, WA ;

EMINI, EA ;

STERN, AM ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2922-2925

[54] SYNTHESIS AND EVALUATION OF 2-PYRIDINONE DERIVATIVES AS HIV-1-SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS .2. ANALOGS OF 3-AMINOPYRIDIN-2(1H)-ONE [J].

SAARI, WS ;

WAI, JS ;

FISHER, TE ;

THOMAS, CM ;

HOFFMAN, JM ;

ROONEY, CS ;

SMITH, AM ;

JONES, JH ;

BAMBERGER, DL ;

GOLDMAN, ME ;

OBRIEN, JA ;

NUNBERG, JH ;

QUINTERO, JC ;

SCHLEIF, WA ;

EMINI, EA ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (21) :3792-3802

[55] NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE-TRANSCRIPTASE - MOLECULAR MODELING AND X-RAY STRUCTURE INVESTIGATIONS [J].

SCHAFER, W ;

FRIEBE, WG ;

LEINERT, H ;

MERTENS, A ;

POLL, T ;

VONDERSAAL, W ;

ZILCH, H ;

NUBER, B ;

ZIEGLER, ML .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (06) :726-732

[56]

Schinazi R. F., 1997, International Antiviral News, V5, P129

[57] AN APPROACH TO COMPUTING ELECTROSTATIC CHARGES FOR MOLECULES [J].

SINGH, UC ;

KOLLMAN, PA .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1984, 5 (02) :129-145

[58]

Stewart J. J. P., 1993, MOPAC 93 00 MANUAL

[59]

STEWART JJP, 1990, MOPAC GEN MOL ORIBIT

[60] CRYSTALLOGRAPHIC EVIDENCE FOR THE EXISTENCE OF C-H...O, C-H...N, AND C-H...C1 HYDROGEN-BONDS [J].

TAYLOR, R ;

KENNARD, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (19) :5063-5070

← 1 2 3 4 5 6 7 →