1-[2-(5-Chloro-2-oxo-benzothiazol-3-yl)-acetyl]-piperidine-4-carboxylic acid | 72735-04-7

• 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: 1-[2-(5-Chloro-2-oxo-benzothiazol-3-yl)-acetyl]-piperidine-4-carboxylic acid
• 英文别名: 1-[2-(5-Chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carboxylic acid；1-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carboxylic acid
• CAS: 72735-04-7
• 化学式: C₁₅H₁₅ClN₂O₄S
• 分子量: 354.814
• InChiKey: URNDSORSHGTTQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2-(5-Chloro-2-oxo-benzothiazol-3-yl)-acetyl]-piperidine-4-carboxylic acid 在 manganese(IV) oxide 、 二甲基硫 、 硼烷 作用下， 生成 1-[2-(5-Chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperidine-4-carbaldehyde
  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 在 sodium hydroxide 、 WSC*HCl 、 1-羟基苯并三唑 、 三乙胺 作用下， 生成 1-[2-(5-Chloro-2-oxo-benzothiazol-3-yl)-acetyl]-piperidine-4-carboxylic acid
  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 receptor. Part 1: 2-oxobenzothiazolin-3-acetic acid derivatives
  作者：Seiichiro Tabuchi、Hiromichi Itani、Yoshihiko Sakata、Hiroko Oohashi、Yoshinari Satoh

  DOI：10.1016/s0960-894x(02)00113-0

  日期：2002.4

  Novel NPY-Y5 antagonist FR73966 was discovered by screening of our in-house chemical library. The analogues were prepared by application of parallel synthesis techniques. Some of the resulting 2-oxobenzo thiazolin-3-acetic acid derivatives exhibited nanomolar binding affinity for human NPY-Y5 receptors. (C) 2002 Elsevier Science Ltd. All rights reserved.