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Structure-activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents.

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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Mizuhara T,Oishi S,Ohno H,Shimura K,Matsuoka M,Fujii N

doi

10.1016/j.bmc.2012.08.030

subject

Has Abstract

pub_date

2012-11-01 00:00:00

pages

6434-41

issue

21

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(12)00652-9

journal_volume

20

pub_type

杂志文章

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