Ethyl 1-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carboxylate | 340179-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: Ethyl 1-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carboxylate
• CAS: 340179-80-8
• 化学式: C₁₇H₁₉ClN₂O₄S
• 分子量: 382.868
• InChiKey: AIVZTJQCOCDDRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 1-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carboxylate 在 manganese(IV) oxide 、 sodium hydroxide 、 二甲基硫 、 硼烷 、 三乙酰氧基硼氢化钠 作用下， 生成
  参考文献：
  名称：

  Novel Potent Antagonists of Human Neuropeptide Y Y5 Receptors. Part 3: 7-Methoxy-1-hydroxy-1-substituted Tetraline Derivatives

  摘要：

  As a part of our continuing research on NPY-Y5 receptor antagonists in the series of novel 6-methoxybenzo[a]cycloheptene derivatives, we discovered a novel skeleton, 7-methoxy-1-hydroxytetraline 7 which had been used as an intermediate, to be more suitable for increasing potencies leading to compound 3 (FR230481). Additionally. we discovered that the naphthalenesulfonamide moiety which was thought to be an essential pharmacophore could be replaced by the 5-chlorobenzothiazolin-3-acetic acid moiety to lead to potent compound 4 (FR233118). The structure-activity relationships on compounds 3, 4 and their related derivatives are described. Unfortunately. although compounds 3 and 4 had very high affinities for Y5 receptors, their poor permeabilities to brain were shown by exo-vivo binding assays when orally administered. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00018-5
• 作为产物：
  描述：

  (5-氯-2-氧代-1,3-苯并噻唑-3(2H)-基)乙酸 、 哌啶-4-甲酸乙酯 在 WSC*HCl 、 1-羟基苯并三唑 、 三乙胺 作用下， 生成 Ethyl 1-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carboxylate
  参考文献：
  名称：

  Novel Potent Antagonists of Human Neuropeptide Y Y5 Receptors. Part 3: 7-Methoxy-1-hydroxy-1-substituted Tetraline Derivatives

  摘要：

  As a part of our continuing research on NPY-Y5 receptor antagonists in the series of novel 6-methoxybenzo[a]cycloheptene derivatives, we discovered a novel skeleton, 7-methoxy-1-hydroxytetraline 7 which had been used as an intermediate, to be more suitable for increasing potencies leading to compound 3 (FR230481). Additionally. we discovered that the naphthalenesulfonamide moiety which was thought to be an essential pharmacophore could be replaced by the 5-chlorobenzothiazolin-3-acetic acid moiety to lead to potent compound 4 (FR233118). The structure-activity relationships on compounds 3, 4 and their related derivatives are described. Unfortunately. although compounds 3 and 4 had very high affinities for Y5 receptors, their poor permeabilities to brain were shown by exo-vivo binding assays when orally administered. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00018-5

文献信息

• Novel Potent Antagonists of Human Neuropeptide Y Y5 Receptors. Part 3: 7-Methoxy-1-hydroxy-1-substituted Tetraline Derivatives
  作者：Hiromichi Itani、Harunobu Ito、Yoshihiko Sakata、Yoshifumi Hatakeyama、Hiroko Oohashi、Yoshinari Satoh

  DOI：10.1016/s0960-894x(02)00018-5

  日期：2002.3

  As a part of our continuing research on NPY-Y5 receptor antagonists in the series of novel 6-methoxybenzo[a]cycloheptene derivatives, we discovered a novel skeleton, 7-methoxy-1-hydroxytetraline 7 which had been used as an intermediate, to be more suitable for increasing potencies leading to compound 3 (FR230481). Additionally. we discovered that the naphthalenesulfonamide moiety which was thought to be an essential pharmacophore could be replaced by the 5-chlorobenzothiazolin-3-acetic acid moiety to lead to potent compound 4 (FR233118). The structure-activity relationships on compounds 3, 4 and their related derivatives are described. Unfortunately. although compounds 3 and 4 had very high affinities for Y5 receptors, their poor permeabilities to brain were shown by exo-vivo binding assays when orally administered. (C) 2002 Elsevier Science Ltd. All rights reserved.