4-[4-(3-cyanophenyl)-2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile | 1215086-04-6

• 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: 4-[4-(3-cyanophenyl)-2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
• 英文别名: 4-[4-(3-cyanophenyl)-2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile；4-[4-(3-cyanophenyl)-2,5-dioxo-4-(prop-2-enoxymethyl)imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
• CAS: 1215086-04-6
• 化学式: C₂₂H₁₅F₃N₄O₃
• 分子量: 440.381
• InChiKey: ULPOMPLTMULRRG-UHFFFAOYSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[4-(3-cyanophenyl)-2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile 在 三氟二甲基硫醚络合物 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-[4-(3-cyanophenyl)-2,5-dioxo-4-hydroxymethyl-3-methylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator

  摘要：

  Structural modification performed on a 4-methyl-4-(4-hydroxyphenyphyl)hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. This led to the identification of (S)-(-)-4-(4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile ((S)-(-)-18a, GLPG0492) evaluated in vivo in a classical model of orchidectomized rat. In this model, (-)-18a exhibited anabolic activity on muscle, strongly dissociated from the androgenic activity on prostate after oral dosing. (-)-18a has very good pharmacokinetic properties, including bioavailability in rat (F > 50%), and is currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm300281x
• 作为产物：
  描述：

  4-溴-2-(三氟甲基)苯甲腈 、 3-[2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-4-yl]benzonitrile 在 氧化铜 氨 、 Brine 、 magnesium sulfate 、 silica gel 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 生成 4-[4-(3-cyanophenyl)-2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  NOVEL IMIDAZOLIDINE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS

  摘要：

  披露了具有以下公式表示的新化合物：其中X，R1，R2a，R2b，R2c，R3aR3b，R4a，R4b，R4c和m1如本文所述。这些化合物可以制备为药物组成物，并可用于哺乳动物，包括人类的预防和治疗多种疾病，例如消瘦，骨质疏松，肌肉萎缩，性欲下降和/或性功能障碍，但不限于此。

  公开号：

  US20120178718A1

文献信息

• [EN] NOVEL IMIDAZOLIDINE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS<br/>[FR] NOUVEAUX COMPOSÉS D'IMIDAZOLIDINE EN TANT QUE MODULATEURS DU RÉCEPTEUR D'ANDROGÈNE
  申请人：GALAPAGOS NV

  公开号：WO2010029119A1

  公开（公告）日：2010-03-18

  Novel compounds are disclosed that have a Formula represented by the following: wherein X, R1, R2a, R2b, R2c, R3a R3b, R4a, R4b, R4c, and ml are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example, cachexia, osteoporosis, sarcopenia, a decline in libido and/or sexual dysfunction.

  揭示了具有以下公式表示的新化合物：其中X、R1、R2a、R2b、R2c、R3a、R3b、R4a、R4b、R4c和ml如本文所述。这些化合物可以制备为药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，例如消瘦、骨质疏松症、肌肉减少、性欲下降和/或性功能障碍。
• Imidazolidine compounds as androgen receptor modulators
  申请人：Galapagos NV

  公开号：US07968581B2

  公开（公告）日：2011-06-28

  Novel compounds are disclosed that have a Formula represented by the following: wherein X, R1, R2a, R2b, R2c, R3a R3b, R4a, R4b, R4c, and m1 are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, cachexia, osteoporosis, sarcopenia, a decline in libido and/or sexual dysfunction.

  披露了具有以下公式表示的新化合物：其中X、R1、R2a、R2b、R2c、R3a、R3b、R4a、R4b、R4c和m1的描述如本文所述。这些化合物可以制备成药物组合物，并可用于预防和治疗哺乳动物，包括人类的各种疾病，例如消瘦症、骨质疏松症、肌肉萎缩症、性欲下降和/或性功能障碍等。
• US7968581B2
  申请人：——

  公开号：US7968581B2

  公开（公告）日：2011-06-28
• US8383608B2
  申请人：——

  公开号：US8383608B2

  公开（公告）日：2013-02-26