摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

N-[(5-Trifluoromethylpyridin-2-yl)]-N'-[2-(1-cyclohexenyl)ethyl]-thiourea

中文名称
——
中文别名
——
英文名称
N-[(5-Trifluoromethylpyridin-2-yl)]-N'-[2-(1-cyclohexenyl)ethyl]-thiourea
英文别名
1-[2-(cyclohexen-1-yl)ethyl]-3-[5-(trifluoromethyl)pyridin-2-yl]thiourea
N-[(5-Trifluoromethylpyridin-2-yl)]-N'-[2-(1-cyclohexenyl)ethyl]-thiourea化学式
CAS
——
化学式
C15H18F3N3S
mdl
——
分子量
329.389
InChiKey
VYPUCGDIZFTIPV-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.7
  • 重原子数:
    22
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.47
  • 拓扑面积:
    69
  • 氢给体数:
    2
  • 氢受体数:
    5

反应信息

  • 作为产物:
    参考文献:
    名称:
    N-[2-(1-cyclohexenyl)ethyl]-N′-[2-(5-bromopyridyl)]-thiourea and N′-[2-(1-cyclohexenyl)ethyl]-N′-[2-(5-chloropyridyl)]- thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1
    摘要:
    We have replaced the pyridyl ring of trovirdine with an alicyclic cyclohexenyl, adamantyl or cis-myrtanyl ring. Only the cyclohexenyl-containing thiourea compound N-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5bromopyridyl)]- thiourea (HI-346) las well as its chlorine-substituted derivative N-[2-(1-cyclohexenyl)ethyl]-N'[2-(5-chloropyridyl)]- thiourea/HI-445) showed RT inhibitory activity. HI-346 and HI-445 effectively inhibited recombinant RT with better IC50 values than other anti-HIV agents tested. The ranking order of efficacy in cell-free RT inhibition assays was: HI-346 (IC50 = 0.4 mu M) > HI-445 (IC50 = 0.5 mu M) > trovirdine (IC50 = 0.8 mu M) > MKC-442 (IC50 = 0.8 mu M) = delavirdine (IC50 1.5 mu M) > nevirapine (IC50 = 23 mu M). In accord with this data, both compounds inhibited the replication of the drug-sensitive HIV-1 strain HTLVIIIB with better IC50 values than other anti-HIV agents tested. The ranking order of efficacy in cellular HIV-1 inhibition assays was: HI-445 = HI-346 (IC50 = 3 nM) > MKC-442 (IC50 = 4 nM) = AZT (IC50 = 4 nM) > trovirdine (IC50 = 7 nM) > delavirdine (IC50 = 9 nM)> nevirapine (IC50 = 34 nM). Surprisingly, the lead compounds HI-346 and HI-445 were 3-times more effective against the multidrug resistant HIV-1 strain RT-MDR with a V106A mutation las well as additional mutations involving the RT residues 74V,41L, and 215Y) than they were against HTLVIIIB with wild-type RT. HI-346 and HI-445 were 20-times more potent than trovirdine, 200-times more potent than AZT, 300-times more potent than MKC-442, 400-times more potent than delavirdine, and 5000-times more potent than nevirapine against the multidrug resistant HIV-1 strain RT-MDR. HI-445 was also tested against the RT Y181C mutant A17 strain of HIV-1 and found to be >7-fold more effective than trovirdine and >1,400-fold more effective than nevirapine or delavirdine. Similarly, both HI-346 and HI-445 were more effective than trovirdine, nevirapine, and delavirdine against the problematic NNI-resistant HIV-1 strain A17-variant with both Y181C and K103N mutations in RT, although their activity was markedly reduced against this strain. Neither compound exhibited significant cytotoxicity at effective concentrations (CC50 >100 mu M). These findings establish the lead compounds HI-346 and HI-445 as potent inhibitors of drug-sensitive as well as multidrug-resistant stains of HIV-1. (C) 1999 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0960-894x(99)00460-6
点击查看最新优质反应信息

文献信息

  • Cyclohexenyl-ethyl-thiourea compounds and use
    申请人:Parker Hughes Institute
    公开号:US20030125331A1
    公开(公告)日:2003-07-03
    Novel CycloHexenyl-Ethyl-Thiourea (CHET) compounds as inhibitors of reverse transcriptase and effective agents for the treatment of HIV infection, including mutant, drug-sensitive, drug-resistant, and multi-drug resistant strains of HIV.
    新型环己烯基乙基硫脲(CHET)化合物作为逆转录酶抑制剂和治疗艾滋病毒感染的有效药物,包括艾滋病毒的变异株、药物敏感株、耐药株和多重耐药株。
  • CYCLOHEXENYL-ETHYL-THIOUREA COMPOUNDS AND USE
    申请人:Parker Hughes Institute
    公开号:EP1194149A1
    公开(公告)日:2002-04-10
  • US6469034B1
    申请人:——
    公开号:US6469034B1
    公开(公告)日:2002-10-22
  • US6774139B1
    申请人:——
    公开号:US6774139B1
    公开(公告)日:2004-08-10
  • [EN] CYCLOHEXENYL-ETHYL-THIOUREA COMPOUNDS AND USE<br/>[FR] COMPOSÉS CYCLOHEXÉNYL-ÉTHYL-THIOURÉE ET LEUR UTILISATION
    申请人:PARKER HUGHES INST
    公开号:WO2000078315A1
    公开(公告)日:2000-12-28
    The use of at least one compound of formula (I) in the manufacture of a medicament for treating drug-resistant HIV in a subject wherein n is 0 to 6; R is H, halogen (C1-C12) alkyl, (C1-C12) alkoxy, amino, cyano, nitro, or hydroxy; and R1 comprises cyclo (C3-C12) alkyl, cyclo (C3-C12) alkenyl, isothiazolyl, tetrazolyl, triazolyl, pyridyl, imidazolyl, phenyl, napthyl, benzoxazolyl, benzimidazolyl, thiazolyl, oxazolyl, benzothiazolyl, pyrazinyl, pyridazinyl, thiadiazolyl, benzotriazolyl, pyrolyl, indolyl, benzothienyl, thienyl, benzofuryl, quinolyl, isoquinolyl, or pyrazolyl; or a pharmaceutically acceptable addition salt thereof.
查看更多

同类化合物

(S)-氨氯地平-d4 (R,S)-可替宁N-氧化物-甲基-d3 (R)-(+)-2,2'',6,6''-四甲氧基-4,4''-双(二苯基膦基)-3,3''-联吡啶(1,5-环辛二烯)铑(I)四氟硼酸盐 (R)-N'-亚硝基尼古丁 (R)-DRF053二盐酸盐 (5E)-5-[(2,5-二甲基-1-吡啶-3-基-吡咯-3-基)亚甲基]-2-亚磺酰基-1,3-噻唑烷-4-酮 (5-溴-3-吡啶基)[4-(1-吡咯烷基)-1-哌啶基]甲酮 (5-氨基-6-氰基-7-甲基[1,2]噻唑并[4,5-b]吡啶-3-甲酰胺) (2S,2'S)-(-)-[N,N'-双(2-吡啶基甲基]-2,2'-联吡咯烷双(乙腈)铁(II)六氟锑酸盐 (2S)-2-[[[9-丙-2-基-6-[(4-吡啶-2-基苯基)甲基氨基]嘌呤-2-基]氨基]丁-1-醇 (2R,2''R)-(+)-[N,N''-双(2-吡啶基甲基)]-2,2''-联吡咯烷四盐酸盐 (1'R,2'S)-尼古丁1,1'-Di-N-氧化物 黄色素-37 麦斯明-D4 麦司明 麝香吡啶 鲁非罗尼 鲁卡他胺 高氯酸N-甲基甲基吡啶正离子 高氯酸,吡啶 高奎宁酸 马来酸溴苯那敏 马来酸氯苯那敏-D6 马来酸左氨氯地平 顺式-双(异硫氰基)(2,2'-联吡啶基-4,4'-二羧基)(4,4'-二-壬基-2'-联吡啶基)钌(II) 顺式-二氯二(4-氯吡啶)铂 顺式-二(2,2'-联吡啶)二氯铬氯化物 顺式-1-(4-甲氧基苄基)-3-羟基-5-(3-吡啶)-2-吡咯烷酮 顺-双(2,2-二吡啶)二氯化钌(II) 水合物 顺-双(2,2'-二吡啶基)二氯化钌(II)二水合物 顺-二氯二(吡啶)铂(II) 顺-二(2,2'-联吡啶)二氯化钌(II)二水合物 韦德伊斯试剂 非那吡啶 非洛地平杂质C 非洛地平 非戈替尼 非布索坦杂质66 非尼拉朵 非尼拉敏 雷索替丁 阿雷地平 阿瑞洛莫 阿扎那韦中间体 阿培利司N-6 阿伐曲波帕杂质40 间硝苯地平 间-硝苯地平 镉,二碘四(4-甲基吡啶)- 锌,二溴二[4-吡啶羧硫代酸(2-吡啶基亚甲基)酰肼]-