(3R,4R)-1-[4-(5-Chloro-1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-butyl]-4-phenyl-piperidine-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R)-1-[4-(5-Chloro-1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-butyl]-4-phenyl-piperidine-3-carboxylic acid ethyl ester
• 英文别名: ethyl (3R,4R)-1-[4-(5-chloro-1,1,3-trioxo-1,2-benzothiazol-2-yl)butyl]-4-phenylpiperidine-3-carboxylate
• 化学式: C₂₅H₂₉ClN₂O₅S
• 分子量: 505.035
• InChiKey: IPBOROXXRHATRV-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三甲基(苯基)锡 在 palladium on activated charcoal N-甲基吡咯烷酮 、 盐酸 、 palladium diacetate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4R)-1-[4-(5-Chloro-1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-butyl]-4-phenyl-piperidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Selective α-1A adrenergic receptor antagonists. effects of pharmacophore regio- and stereochemistry on potency and selectivity

  摘要：

  The anti-anxiety agent ipsapirone has been shown to have modest affinity for alpha-1 receptors. We disclose the discovery of potent alpha-1a receptor subtype selective antagonists based on the ipsapirone structure which possess selectivity versus the 5-HT receptors tested. These antagonists were obtained by tethering a saccharin ring to 4-phenyl-3-carboxyethyl piperidines. The design principles which led to this structural motif are discussed. The synthesis of key analogs, their SAR, as well as results of selected in vitro and in vivo studies are described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00451-x

文献信息

• Selective α-1A adrenergic receptor antagonists. effects of pharmacophore regio- and stereochemistry on potency and selectivity
  作者：Michael A. Patane、Robert M. DiPardo、RoseAnn P. Price、Raymond S.L. Chang、Richard W. Ransom、Stacey S. O'Malley、Jerry Di Salvo、Mark G. Bock

  DOI：10.1016/s0960-894x(98)00451-x

  日期：1998.9

  The anti-anxiety agent ipsapirone has been shown to have modest affinity for alpha-1 receptors. We disclose the discovery of potent alpha-1a receptor subtype selective antagonists based on the ipsapirone structure which possess selectivity versus the 5-HT receptors tested. These antagonists were obtained by tethering a saccharin ring to 4-phenyl-3-carboxyethyl piperidines. The design principles which led to this structural motif are discussed. The synthesis of key analogs, their SAR, as well as results of selected in vitro and in vivo studies are described. (C) 1998 Elsevier Science Ltd. All rights reserved.