(S)-1,2,3,4-四氢异喹啉-3-羧酸苄酯盐酸盐 | 103733-30-8

• 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: (S)-1,2,3,4-四氢异喹啉-3-羧酸苄酯盐酸盐
• 中文别名: 喹那普利二环酸苄酯
• 英文名称: (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid benzylester hydrochloride
• 英文别名: (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester, hydrochloride；(s)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride；benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;hydrochloride
• CAS: 103733-30-8
• 化学式: C₁₇H₁₇NO₂*ClH
• 分子量: 303.788
• InChiKey: HYKDEPCVBMNYCM-NTISSMGPSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1,2,3,4-四氢异喹啉-3-羧酸苄酯盐酸盐 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  The stereochemical requirements of the novel δ-opioid selective dipeptide antagonist TMT-Tic

  摘要：

  Five conformationally constrained dipeptide TMT-L-Tic analogues have been synthesized and evaluated for their bioactivity using in vitro bioassays. The most potent and selective analogue (2S,SR)-TMT-L-Tic showed 9 nM binding affinity and 4000-fold selectivity for the delta vs mu opioid receptor. The lowest-energy conformation of(2S,3R)-TMT-L-Tic is suggested to be bioactive one in which the chi(1) torsional angle is trans for TMT and gauche (+) for Tic. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10145-7
• 作为产物：
  描述：

  N-叔丁氧羰基-(S)-1,2,3,4-四氢异喹啉-3-羧酸 在 盐酸 、 苄基三乙基氯化铵 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 碳酸氢钠 作用下， 以 溶剂黄146 为溶剂， 生成 (S)-1,2,3,4-四氢异喹啉-3-羧酸苄酯盐酸盐
  参考文献：
  名称：

  The stereochemical requirements of the novel δ-opioid selective dipeptide antagonist TMT-Tic

  摘要：

  Five conformationally constrained dipeptide TMT-L-Tic analogues have been synthesized and evaluated for their bioactivity using in vitro bioassays. The most potent and selective analogue (2S,SR)-TMT-L-Tic showed 9 nM binding affinity and 4000-fold selectivity for the delta vs mu opioid receptor. The lowest-energy conformation of(2S,3R)-TMT-L-Tic is suggested to be bioactive one in which the chi(1) torsional angle is trans for TMT and gauche (+) for Tic. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10145-7

文献信息

• [EN] PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMIDES DE N-[1-(S)-(ÉTHOXYCARBONYL)-3-PHÉNYLPROPYL]-L-ALANINE
  申请人：SANOFI AVENTIS DEUTSCHLAND

  公开号：WO2014202659A1

  公开（公告）日：2014-12-24

  A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.

  描述了一种制备N-[1-(S)-(乙氧羰基)-3-苯基丙基]-L-丙氨酸酰胺的方法。该工艺可用于从N-[1-(S)-(乙氧羰基)-3-苯基丙基]-L-丙氨酸出发，通过与适当的胺类反应，生产关键中间体，最终生产ACE抑制剂，如雷米普利、依那普利、喹那普利、群多普利、地拉普利和莫昔普利。
• Studies on neurokinin antagonists. 1. The design of novel tripeptides possessing glutaminyl-D-tryptophylphenylalanine sequence as substance P antagonists
  作者：Daijiro Hagiwara、Hiroshi Miyake、Hiroshi Morimoto、Masako Murai、Takashi Fujii、Masaaki Matsuo

  DOI：10.1021/jm00089a011

  日期：1992.5

  To discover a novel and low molecular weight substance P (SP) antagonist we postulated that the essential binding domain of peptide ligands was only a small portion in the whole structure. On the basis of this assumption, we selected the known octapeptide SP antagonist D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-D-Trp-Phe-NH2 (1) as a lead and synthesized its fragment tripeptides which were evaluated for their activity to block H-3-SP binding on guinea pig lung membranes. The protected tripeptide N(alpha)-[N(alpha)-[N(alpha)-(tert-butyloxycarbonyl)-L-glutaminyl]-N1-formyl-D-tryptophyl]-L-phenylalanine benzyl ester [Boc-Gln-D-Trp(CHO)-Phe-OBzl (4a)], corresponding to the Gln-D-Trp-Phe part of 1, exhibited 7-fold potent inhibitory activity in comparison with 1. Studies on structure-activity relationships revealed that the D-tryptophan, L-phenylalanine, and benzyl ester were quite important to maintain the high binding affinity. It was also indicated that 4a antagonized the SP-induced contraction of isolated guinea pig trachea strips (IC50 = 4.7 x 10(-6) M).