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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 |
| Appears in Collections: | Journal Articles |
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