Inhibitors of HIV-1 attachment. Part 3: A preliminary survey of the effect of structural variation of the benzamide moiety on antiviral activity.
1-(4-Benzoylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione (1a) has been characterized as an inhibitor of HIV-1 attachment that interferes with the interaction of viral gp120 with the host cell receptor CD4. In previous studies, the effect of indole substitution pattern on antiviral activity was probed. In this Letter, the effect of structural variation of the benzamide moiety is described, a study that reveals the potential or the phenyl moiety to be replaced by five-membered heterocyclic rings and a restricted tolerance for the introduction of substituents to the phenyl ring.
Meanwell
Nicholas A
NA
Department of Chemistry, Bristol-Myers Squibb Research and Development, 5 Research Parkway, Wallingford, CT 06492, USA. Nicholas.Meanwell@bms.com
Wallace
Owen B
OB
Wang
Henry
H
Deshpande
Milind
M
Pearce
Bradley C
BC
Trehan
Ashok
A
Yeung
Kap-Sun
KS
Qiu
Zhilei
Z
Wright
J J Kim
JJ
Robinson
Brett A
BA
Gong
Yi-Fei
YF
Wang
Hwei-Gene Heidi
HG
Spicer
Timothy P
TP
Blair
Wade S
WS
Shi
Pei-Yong
PY
Lin
Pin-fang
PF
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001549:Benzamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D015699:HIV Envelope Protein gp120 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D023581:HIV Fusion Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D053585:Virus Attachment / Q000187:drug effects*
C544973:1-(4-benozylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione; D019380:Anti-HIV Agents; D001549:Benzamides; D015699:HIV Envelope Protein gp120; D023581:HIV Fusion Inhibitors; D007211:Indoles; D010879:Piperazines; C514793:gp120 protein, Human immunodeficiency virus 1; C037689:benzamide