3-[2-(2-propenyloxy)acetyl]benzonitrile | 1215086-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-(2-propenyloxy)acetyl]benzonitrile
• 英文别名: 3-(2-Prop-2-enoxyacetyl)benzonitrile；3-(2-prop-2-enoxyacetyl)benzonitrile
• CAS: 1215086-02-4
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: XLYRHBUIAMZFTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 3-[2-(2-propenyloxy)acetyl]benzonitrile 、 ammonium carbonate monohydrate 在 水 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 3-[2,5-dioxo-4-[(2-propenyloxy)methyl]imidazolidin-4-yl]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：

  3-(2-溴乙酰基)苯甲腈 在 calcium sulfate 、 水 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 生成 3-[2-(2-propenyloxy)acetyl]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

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。
• Identification of a 4-(Hydroxymethyl)diarylhydantoin as a Selective Androgen Receptor Modulator
  作者：François Nique、Séverine Hebbe、Nicolas Triballeau、Christophe Peixoto、Jean-Michel Lefrançois、Hélène Jary、Luke Alvey、Murielle Manioc、Christopher Housseman、Hugo Klaassen、Kris Van Beeck、Denis Guédin、Florence Namour、Dominque Minet、Ellen Van der Aar、Jean Feyen、Stephen Fletcher、Roland Blanqué、Catherine Robin-Jagerschmidt、Pierre Deprez

  DOI：10.1021/jm300281x

  日期：2012.10.11

  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.