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Title: Structure-activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents.
Authors: Mizuhara, Tsukasa
Oishi, Shinya
Ohno, Hiroaki
Shimura, Kazuya
Matsuoka, Masao
Fujii, Nobutaka
Author's alias: 大石, 真也
Keywords: Anti-HIV agents
PD 404182
Pyrimidobenzothiazine
Issue Date: 1-Nov-2012
Publisher: Elsevier Ltd.
Journal title: Bioorganic & medicinal chemistry
Volume: 20
Issue: 21
Start page: 6434
End page: 6441
DOI: 10.1016/j.bmc.2012.08.030
Abstract: 3,4-Dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182) is an antiretroviral agent with submicromolar inhibitory activity against human immunodeficiency virus-1 (HIV-1) and HIV-2 infection. In the current study, the structure-activity relationships of accessory groups at the 3- and 9-positions of pyrimido[1,2-c][1,3]benzothiazin-6-imine were investigated for the development of more potent anti-HIV agents. Several different derivatives containing a 9-aryl group were designed and synthesized using Suzuki-Miyaura cross-coupling and Ullmann coupling reactions. Modification of the m-methoxyphenyl or benzo[d][1,3]dioxol-5-yl group resulted in improved anti-HIV activity. In addition, the 2,4-diazaspiro[5.5]undec-2-ene-fused benzo[e][1,3]thiazine derivatives were designed and tested for their anti-HIV activities. The most potent 9-(benzo[d][1,3]dioxol-5-yl) derivative was two-threefold more effective against several strains of HIV-1 and HIV-2 than the parent compound, PD 404182.
Rights: © 2012 Elsevier Ltd.
URI: http://hdl.handle.net/2433/161054
PubMed ID: 23022280
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