IR@PKUHSC  > 北京大学药学院  > 化学生物学系
学科主题药学
The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase
Wang, Xiaowei1; Lou, Qinghua1; Guo, Ying1; Xu, Yang1; Zhang, Zhili1; Liu, Junyi1
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2006
DOI10.1039/b607972p
4期:17页:3252-3258
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]HUMAN-IMMUNODEFICIENCY-VIRUS ; ANNELATED ANALOGS ; ANTI-HIV-1 AGENTS ; INVITRO ; MKC-442 ; TYPE-1 ; 3&prime ; -AZIDO-3&prime ; -DEOXYTHYMIDINE ; REPLICATION ; RESISTANCE ; COMPLEX
英文摘要

Novel compounds, which can be considered as conformationally restricted analogues of MKC-442, have been synthesized and tested as inhibitors of the reverse transcriptase of human immunodeficiency virus type-1 (HIV-1). Reaction of urea with a beta-ketoester furnished 6,7,8,9-tetrahydro-9-phenyl- 1H-cyclohepta[d] pyrimidine-2,4-(3H,5H)-dione (6a) and 6,7,8,9-tetrahydro-9-p-tolyl-1H-cyclohepta[ d] pyrimidine-2,4-( 3H, 5H)-dione (6b) which were then alkylated at the N-1 position with chloromethyl ether, allyl bromide and benzyl bromide to afford the target compounds 7a - b, 8a - b, 9 and 10, respectively. The seven-membered, annelated compounds have a relatively rigid structures and can lock the orientation of the aromatic ring. Chemical modi. cation at N-1 of the pyrinidine ring and the 9-phenyl ring was attempted, with the aim of improving the antiretroviral activity. In particular, replacement of the aliphatic group with the phenyl moiety at the terminus of N-1 side chain can enhance the activity. The most active compounds showed activity in the low micromolar range with IC50 values comparable to that of nevirapine. The biological activity results are in accordance with the docking results.

语种英语
WOS记录号WOS:000239915500014
引用统计
被引频次:18[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/50437
专题北京大学药学院_化学生物学系
北京大学药学院
作者单位1.Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, Beijing 100083, Peoples R China
2.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
推荐引用方式
GB/T 7714
Wang, Xiaowei,Lou, Qinghua,Guo, Ying,et al. The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2006,4(17):3252-3258.
APA Wang, Xiaowei,Lou, Qinghua,Guo, Ying,Xu, Yang,Zhang, Zhili,&Liu, Junyi.(2006).The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase.ORGANIC & BIOMOLECULAR CHEMISTRY,4(17),3252-3258.
MLA Wang, Xiaowei,et al."The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase".ORGANIC & BIOMOLECULAR CHEMISTRY 4.17(2006):3252-3258.
条目包含的文件
条目无相关文件。
个性服务
推荐该条目
保存到收藏夹
查看访问统计
导出为Endnote文件
谷歌学术
谷歌学术中相似的文章
[Wang, Xiaowei]的文章
[Lou, Qinghua]的文章
[Guo, Ying]的文章
百度学术
百度学术中相似的文章
[Wang, Xiaowei]的文章
[Lou, Qinghua]的文章
[Guo, Ying]的文章
必应学术
必应学术中相似的文章
[Wang, Xiaowei]的文章
[Lou, Qinghua]的文章
[Guo, Ying]的文章
相关权益政策
暂无数据
收藏/分享
所有评论 (0)
暂无评论
 

除非特别说明,本系统中所有内容都受版权保护,并保留所有权利。