N-{4-[4-(5-chloro-2-thiophenecarbonyl)-1-piperazinyl]phenyl}-N-[3-(4-cyanobenzyl)-3H-imidazol-4-ylmethyl]-3-methoxybenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-{4-[4-(5-chloro-2-thiophenecarbonyl)-1-piperazinyl]phenyl}-N-[3-(4-cyanobenzyl)-3H-imidazol-4-ylmethyl]-3-methoxybenzamide
• 英文别名: N-{4-[4-(5-Chloro-thiophene-2-carbonyl)-piperazin-1-yl]-phenyl}-N-[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-3-methoxy-benzamide；N-[4-[4-(5-chlorothiophene-2-carbonyl)piperazin-1-yl]phenyl]-N-[[3-[(4-cyanophenyl)methyl]imidazol-4-yl]methyl]-3-methoxybenzamide
• 化学式: C₃₅H₃₁ClN₆O₃S
• 分子量: 651.189
• InChiKey: XGBGDUQBOSFEEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氯噻吩-5-甲酸 在 PS-DIEA 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 N-{4-[4-(5-chloro-2-thiophenecarbonyl)-1-piperazinyl]phenyl}-N-[3-(4-cyanobenzyl)-3H-imidazol-4-ylmethyl]-3-methoxybenzamide
  参考文献：
  名称：

  Synthesis and evaluation of a novel series of farnesyl protein transferase inhibitors as non-peptidic CAAX tetrapeptide analogues

  摘要：

  A novel series of compounds, derived from 4-amino-phenyl piperazine, has been designed to selectively inhibit farnesyl protein transferase (FPTase) as CAAX tetrapeptide analogues. Certain of these compounds were shown to possess low nanomolar inhibitory activity both against the isolated enzyme and in cultured cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00170-7

文献信息

• Novel aminophenyl piperazine or aminophenyl piperidine derivatives inhibiting prenyl transferase proteins and method for preparing same
  申请人：——

  公开号：US20040092524A1

  公开（公告）日：2004-05-13

  The invention concerns compounds corresponding to general formula (I), wherein, in particular: W represents hydrogen, COR 6 , CSR 6 , SO 2 R 6 , CO(CH 2 ) n R 6 , (CH 2 ) n R 7 ; X represents CH or N; Y represents (CH 2 ) n , CO, CH 2 CO, CH═CHCO, CH 2 CH 2 CO; Z represents a heterocycle. When Z=pyridine, then Y is other than CO. R 1 represents hydrogen, C 1 -C 6 alkyl, halogen OCH 3 , CF 3 ; R 2 and R 3 , identical or different, represent hydrogen, C 1 -C 6 alkyl; R 4 represents a) hydrogen, b) C 1 -C 6 alkyl, c) an aryl, d) a heterocycle; R 5 represents hydrogen, COR 7 R 8 , SO 2 R 7 , CO(CH 2 ) n SR 7 , CO(CH 2 ) n OR 7 , CONR 7 R 8 , CO(CH 2 ) m COR 7 ; R 6 represents a) a phenyl or a naphthyl, b) a C 1 -C 6 alkyl, a cycloalkyl, c) a heterocycle, d) NR 7 R 8 ; R 7 and R 8 , identical or different, represent a) hydrogen, C 1 -C 15 alkyl, b) a heterocycle, c) an aryl; n represents 0 to 10; m represents 2 to 10; provided that when Z represents a quinozaline or benzimidazole group, then R 5 is other than CH 2 Ph or methyl and n is other than zero. 1

  该发明涉及与一般式（I）相对应的化合物，其中，特别是：W代表氢，COR6，CSR6，SO2R6，CO（CH2）nR6，（CH2）nR7；X代表CH或N；Y代表（CH2）n，CO，CH2CO，CH═CHCO，CH2CH2CO；Z代表杂环。当Z=吡啶时，Y不是CO。R1代表氢，C1-C6烷基，卤素OCH3，CF3；R2和R3，相同或不同，代表氢，C1-C6烷基；R4代表a）氢，b）C1-C6烷基，c）芳基，d）杂环；R5代表氢，COR7R8，SO2R7，CO（CH2）nSR7，CO（CH2）nOR7，CONR7R8，CO（CH2）mCOR7；R6代表a）苯基或萘基，b）C1-C6烷基，环烷基，c）杂环，d）NR7R8；R7和R8，相同或不同，代表a）氢，C1-C15烷基，b）杂环，c）芳基；n表示0到10；m表示2到10；前提是当Z代表喹唑啉或苯并咪唑基团时，R5不是CH2Ph或甲基，n不是零。
• Synthesis and evaluation of a novel series of farnesyl protein transferase inhibitors as non-peptidic CAAX tetrapeptide analogues
  作者：Michel Perez、Catherine Maraval、Stephan Dumond、Marie Lamothe、Philippe Schambel、Chantal Etiévant、Bridget Hill

  DOI：10.1016/s0960-894x(03)00170-7

  日期：2003.4

  A novel series of compounds, derived from 4-amino-phenyl piperazine, has been designed to selectively inhibit farnesyl protein transferase (FPTase) as CAAX tetrapeptide analogues. Certain of these compounds were shown to possess low nanomolar inhibitory activity both against the isolated enzyme and in cultured cells. (C) 2003 Elsevier Science Ltd. All rights reserved.