(R)-1-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-4-piperidin-4-yl-piperazine | 203180-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (R)-1-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-4-piperidin-4-yl-piperazine
• 英文别名: 1-{1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-4-piperidin-4-yl-piperazine；(2R)-1-[(1S)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethyl]-2-methyl-4-piperidin-4-ylpiperazine
• CAS: 203180-30-7
• 化学式: C₂₅H₃₃N₃O₄S
• 分子量: 471.621
• InChiKey: KSVDOWBNBPBIBU-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-氯噻吩-2-甲酰氯 、 (R)-1-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-4-piperidin-4-yl-piperazine 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [4-((R)-4-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-3-methyl-piperazin-1-yl)-piperidin-1-yl]-(3-chloro-thiophen-2-yl)-methanone
  参考文献：
  名称：

  Synthesis and structure–Activity relationships of M2-Selective muscarinic receptor ligands in the 1-[4-(4-Arylsulfonyl)-phenylmethyl]-4-(4-piperidinyl)-piperazine family

  摘要：

  The synthesis and muscarinic binding properties of compounds based on the 1-[4-(4-arylsulfonyl)phenylmethyl]-4-(1aroyl-4-piperidinyl)-piperazine skeleton are described. For Compounds. substituted with appropriately configured methyl groups at the benzylic center and at the piperazine 2-position. high levels of selective, M-2 subtype affinity could be obtained. particularly when the terminal N-aroyl residue was ortho-substituted. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00024-0
• 作为产物：
  描述：

  (R)-4-Boc-2-甲基哌嗪 在 盐酸 、 tetramethylpiperidine 、 三乙酰氧基硼氢化钠 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 (R)-1-{(S)-1-[4-(Benzo[1,3]dioxole-5-sulfonyl)-phenyl]-ethyl}-2-methyl-4-piperidin-4-yl-piperazine
  参考文献：
  名称：

  Substituted 2-(R)-Methyl piperazines as muscarinic M2 selective ligands

  摘要：

  A novel series of 2-(R)-methyl-substituted piperazines (e.g.. 2) is described. They are potent M-2 selective ligands that have > 100-fold selectivity versus the M-1 receptor. In the rat microdialysis assay. compound 14 showed significantly enhanced levels of acetylcholine after oral administration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00023-9

文献信息

• Synthesis and structure–Activity relationships of M2-Selective muscarinic receptor ligands in the 1-[4-(4-Arylsulfonyl)-phenylmethyl]-4-(4-piperidinyl)-piperazine family
  作者：Stuart W McCombie、Sue-Ing Lin、Jayaram R Tagat、Dennis Nazareno、Susan Vice、Jennifer Ford、Theodros Asberom、Daria Leone、Joseph A Kozlowski、Guowei Zhou、Vilma B Ruperto、Ruth A Duffy、Jean E Lachowicz

  DOI：10.1016/s0960-894x(02)00024-0

  日期：2002.3

  The synthesis and muscarinic binding properties of compounds based on the 1-[4-(4-arylsulfonyl)phenylmethyl]-4-(1aroyl-4-piperidinyl)-piperazine skeleton are described. For Compounds. substituted with appropriately configured methyl groups at the benzylic center and at the piperazine 2-position. high levels of selective, M-2 subtype affinity could be obtained. particularly when the terminal N-aroyl residue was ortho-substituted. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Substituted 2-(R)-Methyl piperazines as muscarinic M2 selective ligands
  作者：Joseph A Kozlowski、Guowei Zhou、Jayaram R Tagat、Sue-Ing Lin、Stuart W McCombie、Vilma B Ruperto、Ruth A Duffy、Robert A McQuade、Gordon Crosby、Lisa A Taylor、William Billard、Herbert Binch、Jean E Lachowicz

  DOI：10.1016/s0960-894x(02)00023-9

  日期：2002.3

  A novel series of 2-(R)-methyl-substituted piperazines (e.g.. 2) is described. They are potent M-2 selective ligands that have > 100-fold selectivity versus the M-1 receptor. In the rat microdialysis assay. compound 14 showed significantly enhanced levels of acetylcholine after oral administration. (C) 2002 Elsevier Science Ltd. All rights reserved.