2-chloro-4-(4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)benzonitrile | 875056-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-chloro-4-(4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)benzonitrile
• 英文别名: 2-Chloro-4-(4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl)benzonitrile
• CAS: 875056-38-5
• 化学式: C₁₂H₁₀ClN₃OS
• 分子量: 279.75
• InChiKey: XYXGOXZJXGSUFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  421.8±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)benzonitrile 、 N,N-dibenzylethenesulfonamide 在 potassium carbonate 作用下， 以 1,3-二甲基-2-咪唑啉酮 为溶剂， 反应 7.0h， 以38%的产率得到C₂₈H₂₇ClN₄O₃S₂
  参考文献：
  名称：

  [EN] NOVEL IMIDAZOLIDINE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS IMIDAZOLIDINE

  摘要：

  通式（I）代表的化合物；以及含有这些化合物的药物和药用组合物：（I）中n是1到20的整数；Q是（II）或（III）A是氰基或类似物；B是氢、卤素或类似物；X1和X2分别独立地从O和S之间选择；E是C1-4烷基；R1、R2、R3和R4分别独立地从氢和C1-6烷基之间选择。

  公开号：

  WO2006013887A1
• 作为产物：
  描述：

  2-氯-4-异硫氰酰基苯氰 、 2-氨基异丁酸乙酯盐酸盐 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以86%的产率得到2-chloro-4-(4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)benzonitrile
  参考文献：
  名称：

  Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer

  摘要：

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem with agonist metabolites, novel thiohydantoin derivatives were identified by applying two strategies. One was the replacement of the alkylsulfonamide moiety by a phenylsulfonamide to avoid the production of agonist metabolites. The other was the replacement of the phenyl ring with a pyridine ring to improve in vivo potency and reduce hERG affinity. Pharmacological assays indicated that CH5137291 (17b) was a potent AR pure antagonist which did not produce the agonist metabolite. Moreover, CH5137291 completely inhibited in vivo tumor growth of LNCaP-BC2, a castration-resistant prostate cancer model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.023

文献信息

• NOVEL IMIDAZOLIDINE DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1775289B1

  公开（公告）日：2011-03-30
• Novel Imidazolidine Derivatives
  申请人：Tachibana Kazutaka

  公开号：US20070249697A1

  公开（公告）日：2007-10-25

  The present invention provides a compound represented by formula (I): wherein n is an integer selected from 1 to 20, Q is A is cyano or the like; B is hydrogen, halogen, or the like; X 1 and X 2 are each independently selected from O and S; E is a C 1-4 alkyl group; and R 1 , R 2 , R 3 and R 4 are each independently selected from a hydrogen atom and a C 1 -C 6 alkyl group, and a drug, a pharmaceutical composition containing the compound, and the like.
• US7803826B2
  申请人：——

  公开号：US7803826B2

  公开（公告）日：2010-09-28
• [EN] NOVEL IMIDAZOLIDINE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS IMIDAZOLIDINE
  申请人：CHUGAI PHARMACEUTICAL CO LTD

  公开号：WO2006013887A1

  公开（公告）日：2006-02-09

  Compounds represented by the general formula (I); and drugs and medicinal compositions, containing the compounds: (I) wherein n is an integer of 1 to 20; Q is (II) or (III) A is cyano or the like; B is hydrogen, halogeno, or the like; X1 and X2 are each independently selected from between O and S; E is C1-4 alkyl; and R1, R2, R3 and R4 are each independently selected from between hydrogen and C1-6 alkyl.

  通式（I）代表的化合物；以及含有这些化合物的药物和药用组合物：（I）中n是1到20的整数；Q是（II）或（III）A是氰基或类似物；B是氢、卤素或类似物；X1和X2分别独立地从O和S之间选择；E是C1-4烷基；R1、R2、R3和R4分别独立地从氢和C1-6烷基之间选择。
• Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer
  作者：Hitoshi Yoshino、Haruhiko Sato、Takuya Shiraishi、Kazutaka Tachibana、Takashi Emura、Akie Honma、Nobuyuki Ishikura、Toshiaki Tsunenari、Miho Watanabe、Ayako Nishimoto、Ryo Nakamura、Toshito Nakagawa、Masateru Ohta、Noriyuki Takata、Kentaro Furumoto、Kazuya Kimura、Hiromitsu Kawata

  DOI：10.1016/j.bmc.2010.10.023

  日期：2010.12

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem with agonist metabolites, novel thiohydantoin derivatives were identified by applying two strategies. One was the replacement of the alkylsulfonamide moiety by a phenylsulfonamide to avoid the production of agonist metabolites. The other was the replacement of the phenyl ring with a pyridine ring to improve in vivo potency and reduce hERG affinity. Pharmacological assays indicated that CH5137291 (17b) was a potent AR pure antagonist which did not produce the agonist metabolite. Moreover, CH5137291 completely inhibited in vivo tumor growth of LNCaP-BC2, a castration-resistant prostate cancer model. (C) 2010 Elsevier Ltd. All rights reserved.