[(S)-1-Benzyl-2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester | 372524-05-5

• 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: [(S)-1-Benzyl-2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 372524-05-5
• 化学式: C₂₅H₃₂N₂O₅
• 分子量: 440.539
• InChiKey: BKSRGOGZLJSNGI-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-Benzyl-2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-2-Amino-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-3-phenyl-propan-1-one; hydrochloride
  参考文献：
  名称：

  N- Acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: The first orexin-2 receptor selective non-peptidic antagonist

  摘要：

  The identification of potent and selective orexin-2 receptor (OX2R) antagonists is described based on the modification of N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline analogue 1, recently discovered during high throughput screening (HTS). Substitution of an acyl group in 1 with tert-Leucine (tert-Leu), and introduction of a 4-pyridylmethyl substituent onto the amino function of tert-Leu improved compound potency, selectivity, and water solubility. Thus, compound 29 is a promising tool to investigate the role of orexin-2 receptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.038
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 6,7-二甲氧基-1,2,3,4-四氢异喹啉盐酸盐 在 吡啶 、 4-二甲氨基吡啶 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 生成 [(S)-1-Benzyl-2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  N- Acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: The first orexin-2 receptor selective non-peptidic antagonist

  摘要：

  The identification of potent and selective orexin-2 receptor (OX2R) antagonists is described based on the modification of N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline analogue 1, recently discovered during high throughput screening (HTS). Substitution of an acyl group in 1 with tert-Leucine (tert-Leu), and introduction of a 4-pyridylmethyl substituent onto the amino function of tert-Leu improved compound potency, selectivity, and water solubility. Thus, compound 29 is a promising tool to investigate the role of orexin-2 receptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.038

文献信息

• N- Acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline: The first orexin-2 receptor selective non-peptidic antagonist
  作者：Masaaki Hirose、Shin-ichiro Egashira、Yasuhiro Goto、Takashi Hashihayata、Norikazu Ohtake、Hisashi Iwaasa、Mikiko Hata、Takehiro Fukami、Akio Kanatani、Koji Yamada

  DOI：10.1016/j.bmcl.2003.08.038

  日期：2003.12

  The identification of potent and selective orexin-2 receptor (OX2R) antagonists is described based on the modification of N-acyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline analogue 1, recently discovered during high throughput screening (HTS). Substitution of an acyl group in 1 with tert-Leucine (tert-Leu), and introduction of a 4-pyridylmethyl substituent onto the amino function of tert-Leu improved compound potency, selectivity, and water solubility. Thus, compound 29 is a promising tool to investigate the role of orexin-2 receptors. (C) 2003 Elsevier Ltd. All rights reserved.