(3S)-3-氨基-3,4-二氢-1H-喹啉-2-酮,盐酸盐 | 35987-81-6

• 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
• 中文名称: (3S)-3-氨基-3,4-二氢-1H-喹啉-2-酮,盐酸盐
• 英文名称: (3S)-3-amino-3,4-dthydroquinolin-2(1H)-one hydrochloride
• 英文别名: (S)-3-amino-3,4-dihydro-1H-quinolin-2-one hydrochloride；(S)-3-Amino-3,4-dihydroquinolin-2(1H)-one hydrochloride；(3S)-3-amino-3,4-dihydro-1H-quinolin-2-one;hydrochloride
• CAS: 35987-81-6
• 化学式: C₉H₁₀N₂O*ClH
• 分子量: 198.652
• InChiKey: OKOGJVZTZMRXRG-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-3-氨基-3,4-二氢-1H-喹啉-2-酮,盐酸盐 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 [(S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors

  摘要：

  A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.

  DOI：

  10.1016/j.bmcl.2006.10.037
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、300.0 kPa 条件下， 反应 45.0h， 生成 (3S)-3-氨基-3,4-二氢-1H-喹啉-2-酮,盐酸盐
  参考文献：
  名称：

  Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors

  摘要：

  A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.

  DOI：

  10.1016/j.bmcl.2006.10.037

文献信息

• [EN] TRICYCLIC COMPOUNDS AS KAT II INHIBITORS<br/>[FR] COMPOSÉS TRICYCLIQUES EN TANT QU'INHIBITEURS DE KAT II
  申请人：PFIZER

  公开号：WO2013186666A1

  公开（公告）日：2013-12-19

  Compounds of Formula (I), wherein R1, R 2, X1, Y1, Z1, and Z2 are as defined herein, and pharmaceutically acceptable salts thereof, are described as useful for the treatment of cognitive deficits associated with schizophrenia and other psychiatric, neurodegenerative and/or neurological disorders in mammals, including humans.

  该文描述了式(I)的化合物及其药学上可接受的盐，其中R1、R2、X1、Y1、Z1和Z2的定义如本文所述，可用于治疗哺乳动物，包括人类中与精神分裂症和其他精神、神经退行性和/或神经性疾病相关的认知缺陷。
• PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDES
  申请人：Krulle Thomas Martin

  公开号：US20090099176A1

  公开（公告）日：2009-04-16

  Compounds represented by Formula (I) or pharmaceutically acceptable salts thereof, are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.

  式(I)所代表的化合物或其药学上可接受的盐，可用于预防或治疗糖尿病、高血糖、高胆固醇血症、高胰岛素血症、高脂血症、高血压、动脉粥样硬化或组织缺血，例如心肌缺血，并作为心脏保护剂。
• TRICYCLIC COMPOUNDS AS KAT II INHIBITORS
  申请人：PFIZER INC.

  公开号：US20150175603A1

  公开（公告）日：2015-06-25

  Compounds of Formula (I), wherein R 1 , R 2 , X 1 , Y 1 , Z 1 , and Z 2 are as defined herein, and pharmaceutically acceptable salts thereof, are described as useful for the treatment of cognitive deficits associated with schizophrenia and other psychiatric, neurodegenerative and/or neurological disorders in mammals, including humans.

  公式（I）的化合物，其中R1，R2，X1，Y1，Z1和Z2如此定义，并且其药学上可接受的盐，被描述为用于治疗哺乳动物，包括人类，患有精神分裂症和其他精神、神经退行性和/或神经系统疾病相关的认知缺陷的有用化合物。
• A practical synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one
  作者：Bernard Hulin、Michael G Lopaze

  DOI：10.1016/j.tetasy.2004.05.013

  日期：2004.6

  Asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester with 2-nitrobenzyl bromide followed by reductive cyclization provides (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one in high yield and high enantiomeric excess. (C) 2004 Published by Elsevier Ltd.
• Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors
  作者：Alan M. Birch、Peter W. Kenny、Nikos G. Oikonomakos、Ludovic Otterbein、Paul Schofield、Paul R.O. Whittamore、Dave P. Whalley

  DOI：10.1016/j.bmcl.2006.10.037

  日期：2007.1

  A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.