4-amino-3-(5-chlorothien-2-yl)butanoic acid | 133933-81-0

• 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: 4-amino-3-(5-chlorothien-2-yl)butanoic acid
• 英文别名: 4-azaniumyl-3-(5-chlorothiophen-2-yl)butanoate
• CAS: 133933-81-0
• 化学式: C₈H₁₀ClNO₂S
• 分子量: 219.692
• InChiKey: CDFQDLUHBLZCGL-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  5-氯噻吩-2-甲醛 在 镍 sodium hydroxide 、 氢气 、 苄基三甲基氢氧化铵 作用下， 以 苯 为溶剂， 反应 26.0h， 生成 4-amino-3-(5-chlorothien-2-yl)butanoic acid
  参考文献：
  名称：

  3-Thienyl- and 3-furylaminobutyric acids. Synthesis and binding GABAB receptor studies

  摘要：

  Baclofen (beta-(p-chlorophenyl)-GABA) is a selective agonist for the bicuculline-insensitive GABA(B) receptor. The search for new compounds that bind to the GABA(B) receptor is very important to clarify structural requirements. We report herein the synthesis and the binding studies of variously substituted 3-thienyl- and 3-furylaminobutyric acids. 4-Amino-3-(5-methyl-2-thienyl)butyric acid (5d) and 4-amino-3-(5-chloro-2-thienyl)butyric acid (5h) are potent and specific ligands for GABA(B) receptor. The IC50 values for the displacement of (R)-(-)-[H-3]baclofen are 1.34 and 0.61-mu-M for 5d and 5h, respectively, as compared to 0.33-mu-M for baclofen.

  DOI：

  10.1021/jm00112a033

文献信息

• Use of GABA and GABAB agonists
  申请人：Tufts University

  公开号：US20030162754A1

  公开（公告）日：2003-08-28

  The present invention provides methods of stimulating tissue growth, including islet cell growth, by administering GABA or a GABA agonist to act on GABA B receptors and GABA B -like receptors to activate cell replication.

  本发明提供了通过给予GABA或GABA激动剂以作用于GABA B 受体和类GABA B 受体来促进组织生长，包括胰岛细胞生长的方法，以激活细胞复制。
• Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use
  申请人：Gallop A. Mark

  公开号：US20060111325A1

  公开（公告）日：2006-05-25

  Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, pharmaceutical compositions comprising acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of making prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of using prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

  3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的酰氧烷基氨基甲酸酯前药，包括3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的酰氧烷基氨基甲酸酯前药的药物组合物，制备3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的前药的方法，使用3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的前药的方法，以及用于治疗或预防痉挛或胃食管反流病等疾病或紊乱的药物组合物。还公开了适用于口服的酰氧烷基氨基甲酸酯前药、3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的持续释放口服剂型。
• Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use
  申请人：Gallop A. Mark

  公开号：US20060111439A1

  公开（公告）日：2006-05-25

  Acyloxyalkyl carbamate prodrugs of 3-aminopropylsulfinic acid and analogs thereof, pharmaceutical compositions of 3-aminopropylsulfinic acid and analogs thereof, methods of making prodrugs of 3-aminopropylsulfinic acid and analogs thereof, methods of using prodrugs of 3-aminopropylsulfinic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylsulfinic acid and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

  3-氨基丙磺酸及其类似物的酰氧烷基氨基甲酸酯前药，3-氨基丙磺酸及其类似物的药物组合物，制备3-氨基丙磺酸及其类似物的前药的方法，使用3-氨基丙磺酸及其类似物的前药的方法，以及用于治疗或预防痉挛性或胃食管反流病等疾病或紊乱的药物组合物已被披露。此外，还披露了适用于口服的3-氨基丙磺酸及其类似物的酰氧烷基氨基甲酸酯前药和持续释放口服剂型。
• METHODS OF TREATING FRAGILE X SYNDROME, DOWN'S SYNDROME, AUTISM AND RELATED DISORDERS
  申请人：Wustrow David J.

  公开号：US20120016021A1

  公开（公告）日：2012-01-19

  Disclosed herein are methods of treating fragile X syndrome, fragile X-associated tremor/ataxia syndrome, Down's syndrome and other forms of mental retardation, and/or autism comprising administering a GABA B agonist prodrug to a subject suffering therefrom. The GABA B agonist prodrugs can be compounds of Formula (I), (II) or (III) as disclosed herein.

  本文披露了治疗脆性X综合症、脆性X相关性震颤/共济失调综合症、唐氏综合症和其他形式智力障碍和/或自闭症的方法，包括向患者施用GABAB受体激动剂前药。GABAB受体激动剂前药可以是公式(I)、(II)或(III)中所披露的化合物。
• Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
  申请人：Gallop A. Mark

  公开号：US20050107334A1

  公开（公告）日：2005-05-19

  The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof.

  本文涉及的内容通常与(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的酰氧基烷基氨基甲酸酯前药、其制药组合物、制备(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的前药的方法、使用(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的前药的方法，以及治疗或预防常见疾病和/或疾病，如痉挛和/或酸反流病的制药组合物。本文还涉及适用于口服和口服缓释剂型的(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的酰氧基烷基氨基甲酸酯前药。