3-[3-[1-[(3R)-1-ethylpiperidin-3-yl]-4-methyl-5-phenylimidazol-2-yl]phenyl]-N-hydroxyprop-2-enamide | 858945-17-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[3-[1-[(3R)-1-ethylpiperidin-3-yl]-4-methyl-5-phenylimidazol-2-yl]phenyl]-N-hydroxyprop-2-enamide
• CAS: 858945-17-2
• 化学式: C₂₆H₃₀N₄O₂
• 分子量: 430.55
• InChiKey: ACVQEBXNNLXAGR-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 camphorsulfonic acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-[3-[1-[(3R)-1-ethylpiperidin-3-yl]-4-methyl-5-phenylimidazol-2-yl]phenyl]-N-hydroxyprop-2-enamide
  参考文献：
  名称：

  Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity

  摘要：

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.092

文献信息

• Histone deacetylase inhibitors
  申请人：Bressi C. Jerome

  公开号：US20050159470A1

  公开（公告）日：2005-07-21

  Histone deacetylase inhibitors and uses thereof are provided that have the general Z-Q-L-M wherein Z is a 5-membered aromatic heterocycle as shown herein, each X is independently selected from the group consisting of CR 5 and N; each Y is independently selected from the group consisting of O, S and NR 5 ; R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein; Q is a substituted or unsubstituted aromatic ring; M is a substituent capable of complexing with a protein metal ion; and L is a substituent comprising a chain of 1-10 atoms connecting the M substituent to the Q substituent.

  提供了组成为一般Z-Q-L-M的组合物和使用组合物的组合物，其中Z是如下所示的5元芳香杂环，每个X独立地选择自CR5和N的组；每个Y独立地选择自O，S和NR5的组；R1，R2，R3，R4和R5如此定义；Q是取代或未取代的芳香环；M是能够与蛋白质金属离子络合的取代基；L是包括由1-10个原子构成的链的取代基，将M取代基与Q取代基连接起来。
• [EN] N- HYDROXY-3-(3-(1H-IMIDAZOL-2-YL)-PHENYL)-ACRYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS HISTONE DEACETYLASE (HDAC) INHIBITORS FOR THE TREATMENT OF CANCER<br/>[FR] DERIVES DE N-HYDROXY-3-(3-(1H-IMIDAZOL-2-YL)-PHENYL)-ACRYLAMIDE ET COMPOSES ASSOCIES EN TANT QU'INHIBITEURS D'HISTONE DEACETYLASE POUR LE TRAITEMENT DU CANCER
  申请人：SYRRX INC

  公开号：WO2005065681A1

  公开（公告）日：2005-07-21

  HDAC inhibitors of the present invention are provided that comprise the formula (I) wherein Z is selected from the group consisting of (II) (III) (IV) (V) (VI) (VII) (VIII) (IX) (X) (XI) wherein each X is independently selected from the group consisting of CR5 and N; each Y is independently selected from the group consisting of O, S and NR5; Q is a substituted or unsubstituted aromatic ring; M is a substituent capable of complexing with a histone deacetylase catalytic site and/or a metal ion; and L is a substituent comprising a chain of 1-10 atoms connecting the M substituent to the Q substituent; the other substituents are defined in the claims. The compounds are useful for the treatment of cancer and inflammations.