3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-N-hydroxyacrylamide

• 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: 3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-N-hydroxyacrylamide
• 英文别名: E-3-[3'-(1-adamantyl)-4'-hydroxy-biphenyl-4-yl]-N-hydroxy-acrylamide；(E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]-N-hydroxyprop-2-enamide
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: UGGXMNLTFKYUMB-FPYGCLRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  阿达罗汀 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 盐酸羟胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-N-hydroxyacrylamide
  参考文献：
  名称：

  WO2007/383

  摘要：

  公开号：

文献信息

• Biphenyl and Naphthyl-Phenyl Hydroxamic Acid Derivatives
  申请人：Pisano Claudio

  公开号：US20080319082A1

  公开（公告）日：2008-12-25

  Biphenyl and phenyl-naphthyl compounds bearing a hydroxamic group, which are endowed with antitumour, and anti-angiogenic activity These compounds are therefore particularly useful for the treatment of drug-resistant tumours.

  苯基联苯和苯基萘化合物带有羟肟基，具有抗肿瘤和抗血管生成活性。因此，这些化合物特别适用于治疗耐药性肿瘤。
• Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors
  作者：Raffaella Cincinelli、Loana Musso、Giuseppe Giannini、Valentina Zuco、Michelandrea De Cesare、Franco Zunino、Sabrina Dallavalle

  DOI：10.1016/j.ejmech.2014.04.021

  日期：2014.5

  To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116. (c) 2014 Elsevier Masson SAS. All rights reserved.
• BIPHENYL AND NAPHTHYL-PHENYL HYDROXAMIC ACID DERIVATIVES
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP1896399A1

  公开（公告）日：2008-03-12
• US7728039B2
  申请人：——

  公开号：US7728039B2

  公开（公告）日：2010-06-01
• [EN] BIPHENYL AND NAPHTHYL-PHENYL HYDROXAMIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDES HYDROXAMIQUES BIPHÉNYLES ET NAPHTHYLES-PHÉNYLES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2007000383A1

  公开（公告）日：2007-01-04

  [EN] Biphenyl and phenyl-naphthyl compounds bearing a hydroxamic group, which are endowed with antitumour, and anti-angiogenic activity These compounds are therefore particularly useful for the treatment of drug-resistant tumours.
  [FR] La présente invention concerne des composés biphényles et phényles-naphthyles portant un groupe hydroxamique, qui présentent des activités antitumorales et antiangiogenèses. Ainsi, ces composés se révèlent particulièrement utiles lors du traitement de tumeurs résistant aux médicaments.