(3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione | 262295-89-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione
• 英文别名: (3S,6R)-1-benzyl-3,6-dimethyl-piperazine-2,5-dione
• CAS: 262295-89-6
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: DZTKNEGTYYCOAH-VHSXEESVSA-N

物化性质

• 沸点：
  491.4±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione 在 吡啶 、 lithium aluminium tetrahydride 、 1-氯乙基氯甲酸酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 (+)-(2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  (+)-(2R,5S)-4-[4-Cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3- yl]piperazine-1-carboxamide (YM580) as an Orally Potent and Peripherally Selective Nonsteroidal Androgen Receptor Antagonist

  摘要：

  A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.

  DOI：

  10.1021/jm050293c
• 作为产物：
  描述：

  苯甲醛 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 66.25h， 生成 (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione
  参考文献：
  名称：

  WO2007/109238

  摘要：

  公开号：

文献信息

• Cyanophenyl derivative
  申请人：Yamanouchi Pharmaceutical Co. Ltd.

  公开号：US06673799B1

  公开（公告）日：2004-01-06

  This application relates to a piperazino-substituted novel cyanophenyl derivative in which a substituted carbamoyl or substituted sulfamoyl group having an aryl, heterocyclic or the like group that may have a substituent group is bonded to one nitrogen atom on the piperazine ring. The compound of this application has an anti-androgen action and is useful in preventing or treating prostatic cancer, benign prostatic hyperplasia and the like diseases.

  该申请涉及一种哌嗪取代的新型氰基苯基衍生物，其中带有芳基、杂环或类似的基团的取代羰酰基或取代磺酰基与哌嗪环上的一个氮原子结合。该申请的化合物具有抗雄激素作用，并可用于预防或治疗前列腺癌、良性前列腺增生等疾病。
• [EN] PIPERAZINE DERIVATIVES AND THEIR USE AS MODULATORS OF NUCLEAR HORMONE RECEPTOR FUNCTION<br/>[FR] DERIVES DE PIPERAZINE ET LEUR UTILISATION COMME MODULATEURS DE LA FONCTION DE RECEPTEUR HORMONAL NUCLEAIRE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005040136A1

  公开（公告）日：2005-05-06

  The present invention provides piperazine derivatives and methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders.

  本发明提供了哌嗪衍生物及其在治疗核激素受体相关疾病，如癌症和免疫紊乱中的应用方法。
• Piperazine derivatives and their use as modulators of nuclear hormone receptor function
  申请人：Salvati E. Mark

  公开号：US20050124625A1

  公开（公告）日：2005-06-09

  The present invention provides piperazine derivatives and methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders.

  本发明提供了哌嗪衍生物及其在治疗核激素受体相关疾病，如癌症和免疫失调方面使用的方法。
• CYANOPHENYL DERIVATIVES
  申请人：Astellas Pharma Inc.

  公开号：EP1122242B1

  公开（公告）日：2008-01-16
• US6673799B1
  申请人：——

  公开号：US6673799B1

  公开（公告）日：2004-01-06