4-[(2-{(4S)-4-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid | 494222-50-3

• 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: 4-[(2-{(4S)-4-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid
• 英文别名: (15α,13E)-9-oxo-15-hydroxy-16-(3-chlorophenyl)-17,18,19,20-tetranor-5-thia-8-aza-10-oxaprost-13-enoic acid；4-[2-[(4S)-4-[(E,3S)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl]ethylsulfanyl]butanoic acid
• CAS: 494222-50-3
• 化学式: C₁₉H₂₄ClNO₅S
• 分子量: 413.922
• InChiKey: WEOQVAPKGAQVKA-YMPXZSTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  S-(2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl) ethanethioate 在 硼烷四氢呋喃络合物 、 茴香硫醚 、 potassium tert-butylate 、 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 31.41h， 生成 4-[(2-{(4S)-4-[(1E,3S)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

  摘要：

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.009

文献信息

• Selective D1/D5 receptor antagonists for the treatment of obesity and CNS disorders
  申请人：Burnett A. Duane

  公开号：US20050075325A1

  公开（公告）日：2005-04-07

  The present invention provides compounds, which, are novel antagonists for D 1 /D 5 receptors as well as methods for preparing such compounds. In another embodiment, the invention provides pharmaceutical compositions comprising such D 1 /D 5 receptor antagonists as well as methods of using them to treat CNS disorders, obesity, metabolic disorders, eating disorders such as hyperphagia, and diabetes.

  本发明提供了一种新型D1/D5受体拮抗剂化合物，以及制备这种化合物的方法。在另一实施方式中，该发明提供了包含这种D1/D5受体拮抗剂的药物组合物，以及使用它们来治疗中枢神经系统疾病、肥胖症、代谢性疾病、食欲紊乱疾病（如暴食症）和糖尿病的方法。
• PHARMACEUTICAL COMPOSITION FOR TREATMENT OF DISEASES ASSOCIATED WITH DECREASE IN BONE MASS COMPRISING EP4 AGONIST AS ACTIVE INGREDIENT
  申请人：MARUYAMA Toru

  公开号：US20100010222A1

  公开（公告）日：2010-01-14

  A pharmaceutical composition for topical administration for prevention and/or treatment of diseases associated with decrease in bone mass comprising an EP 4 agonist as an active ingredient. An EP 4 agonist, in which includes a compound possessing prostaglandin skeleton as a representative, possesses promoting action on bone formation, so it is useful for prevention and/or treatment of diseases associated with decrease in bone mass (bone diseases such as primary osteoporosis, secondary osteoporosis, bone metastasis of cancer, hypercalcemia, Paget's disease, bone loss and bone necrosis, postoperative osteogenesis, alternative therapy for bone grafting).

  一种用于局部治疗预防和/或治疗与骨量减少相关疾病的药物组合物，包括EP4激动剂作为活性成分。EP4激动剂，其中包括具有前列腺素骨架的化合物作为代表，具有促进骨形成的作用，因此对于预防和/或治疗与骨量减少相关的疾病（如原发性骨质疏松症、继发性骨质疏松症、骨癌转移、高钙血症、帕吉特病、骨丢失和骨坏死、术后骨生成、骨移植替代疗法）非常有用。
• COMPOSITIONS AND IMPROVED SOFT TISSUE REPLACEMENT METHODS
  申请人：Van Epps Dennis E.

  公开号：US20120269777A1

  公开（公告）日：2012-10-25

  The specification discloses compositions and methods for treating a soft tissue defect of an individual.

  该规范公开了用于治疗个体软组织缺陷的组成物和方法。
• METHODS OF TREATING SOFT TISSUE DEFECTS
  申请人：Allergan, Inc.

  公开号：US20140179752A1

  公开（公告）日：2014-06-26

  The specification discloses compositions and methods for treating a soft tissue defect of an individual.

  该规范公开了治疗个体软组织缺陷的组成物和方法。
• Pharmaceutical composition for treatment of diseases associated with decrease in bone mass comprising EP4 agonist as active ingredient
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：EP2255829A2

  公开（公告）日：2010-12-01

  A pharmaceutical composition for topical administration for prevention and/or treatment of diseases associated with decrease in bone mass comprising an EP4 agonist as an active ingredient. An EP4 agonist, in which includes a compound possessing prostaglandin skeleton as a representative, possesses promoting action on bone formation, so it is useful for prevention and/or treatment of diseases associated with decrease in bone mass (bone diseases such as primary osteoporosis, secondary osteoporosis, bone metastasis of cancer, hypercalcemia, Paget's disease, bone loss and bone necrosis, postoperative osteogenesis, alternative therapy for bone grafting).

  一种局部用药的药物组合物，用于预防和/或治疗与骨量减少有关的疾病，其活性成分包括一种 EP4 激动剂。EP4激动剂（其中包括以前列腺素骨架为代表的化合物）具有促进骨形成的作用，因此可用于预防和/或治疗与骨量减少有关的疾病（骨病，如原发性骨质疏松症、继发性骨质疏松症、癌症骨转移、高钙血症、Paget病、骨丢失和骨坏死、术后成骨、植骨替代疗法）。