Naphthalene-1-sulfonic acid [2-(4-hydroxymethyl-piperidin-1-yl)-ethyl]-amide | 345954-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthalene-1-sulfonic acid [2-(4-hydroxymethyl-piperidin-1-yl)-ethyl]-amide
• 英文别名: N-[2-[4-(hydroxymethyl)piperidin-1-yl]ethyl]naphthalene-1-sulfonamide
• CAS: 345954-70-3
• 化学式: C₁₈H₂₄N₂O₃S
• 分子量: 348.466
• InChiKey: CKCZWCVOVYIRHF-UHFFFAOYSA-N

物化性质

• 沸点：
  552.4±56.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Naphthalene-1-sulfonic acid [2-(4-hydroxymethyl-piperidin-1-yl)-ethyl]-amide 在 manganese(IV) oxide 作用下， 生成 Naphthalene-1-sulfonic acid [2-(4-formyl-piperidin-1-yl)-ethyl]-amide
  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：

  1-[2-(Naphthalene-1-sulfonylamino)-acetyl]-piperidine-4-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 生成 Naphthalene-1-sulfonic acid [2-(4-hydroxymethyl-piperidin-1-yl)-ethyl]-amide
  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