<4-(benzenesulfonimido)-n-butyl>triphenylphosphonium bromide | 52533-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <4-(benzenesulfonimido)-n-butyl>triphenylphosphonium bromide
• 英文别名: [5-(Benzenesulfonamido)-5-oxopentyl]-triphenylphosphanium;bromide
• CAS: 52533-83-2
• 化学式: Br*C₂₉H₂₉NO₃PS
• 分子量: 582.498
• InChiKey: GXQITZYUWTXUBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 、 <4-(benzenesulfonimido)-n-butyl>triphenylphosphonium bromide 在 sodium methylsulfinylcarbanide 作用下， 生成
  参考文献：
  名称：

  N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

  摘要：

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

  DOI：

  10.1021/jm00143a018
• 作为产物：
  描述：

  苯磺酰胺 生成 <4-(benzenesulfonimido)-n-butyl>triphenylphosphonium bromide
  参考文献：
  名称：

  羧基末端修饰的前列腺素类似物的合成及其生物学活性。

  摘要：

  评估了在羧基末端用四唑，酰胺，酰脲，酰亚胺和磺酰亚胺官能团修饰的一系列PGE2、16,16-二甲基-PGE2和PGF2α类似物的子宫刺激性，支气管扩张剂，降压，胃抗分泌和腹泻活性。这些化合物是通过将已知的半缩醛与衍生自必需的取代phospho盐的叶立德缩合为关键步骤，通过修饰Corey前列腺素合成制备的。结构与活性之间的关系表明，C-1位置的质子似乎是激动剂活性所必需的，并且该质子的酸度对活性的影响比悬垂的空间体积更大。

  DOI：

  10.1021/jm00197a012

文献信息

• US4847370A
  申请人：——

  公开号：US4847370A

  公开（公告）日：1989-07-11
• N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants
  作者：Thomas K. Schaaf、Jasjit S. Bindra、James F. Eggler、Jacob J. Plattner、A. James Nelson、M. Ross Johnson、Jay W. Constantine、Hans-Juergen Hess、Walter Elger

  DOI：10.1021/jm00143a018

  日期：1981.11

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).
• Synthesis and biological activity of carboxyl-terminus modified prostaglandin analogs
  作者：Thomas K. Schaaf、Hans Juergen Hess

  DOI：10.1021/jm00197a012

  日期：1979.11

  of PGE2, 16,16-dimethyl-PGE2, and PGF2 alpha analogues modified at the carboxyl terminus with tetrazole, amide, acylurea, imide, and sulfonimide functionalities was evaluated for uterine stimulant, bronchodilator, hypotensive, gastric antisecretory, and diarrheal activity. These compounds were prepared by modification of the Corey prostaglandin synthesis utilizing as a key step condensation of known

  评估了在羧基末端用四唑，酰胺，酰脲，酰亚胺和磺酰亚胺官能团修饰的一系列PGE2、16,16-二甲基-PGE2和PGF2α类似物的子宫刺激性，支气管扩张剂，降压，胃抗分泌和腹泻活性。这些化合物是通过将已知的半缩醛与衍生自必需的取代phospho盐的叶立德缩合为关键步骤，通过修饰Corey前列腺素合成制备的。结构与活性之间的关系表明，C-1位置的质子似乎是激动剂活性所必需的，并且该质子的酸度对活性的影响比悬垂的空间体积更大。