1-(4-tert-butylbenzene)sulfonyl-cis-2,6-dimethylpiperidine | 1189036-66-5

• 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: 1-(4-tert-butylbenzene)sulfonyl-cis-2,6-dimethylpiperidine
• 英文别名: 1-(4-Tert-butyl benzene)-sulfonyl-cis-2,6-dimethyl piperidine；(2S,6R)-1-(4-tert-butylphenyl)sulfonyl-2,6-dimethylpiperidine
• CAS: 1189036-66-5
• 化学式: C₁₇H₂₇NO₂S
• 分子量: 309.473
• InChiKey: HOUVPLOZMHLJPB-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对叔丁基苯磺酰氯 、 (2R,6S)-2,6-dimethylpiperidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到1-(4-tert-butylbenzene)sulfonyl-cis-2,6-dimethylpiperidine
  参考文献：
  名称：

  Active site directed docking studies: Synthesis and pharmacological evaluation of cis-2,6-dimethyl piperidine sulfonamides as inhibitors of acetylcholinesterase

  摘要：

  Hypocholinergic function associated with Alzheimer's disease (AD) is well-accepted hypothesis, in this regard, many research attempts have been made to elevate the reduced cholinergic neurotransmission, among them two main treatment strategies were widely explored, namely stimulation of muscarinic receptor 1 and/or reversible inhibition of acetylcholinesterase (AChE) enzyme. In an attempt to improve the efficacy and to minimize general side effects of these ACNE inhibitors, many lead molecules are developed in research; one among them is piperidine derivative. Donazepil is a widely prescribed ACNE inhibitor which displays a piperidine ring in its structure. In the present study, we have docked cis-2,6-dimethyl piperidine sulfonamides (3a-i) on ACNE enzyme and synthesized by nucleophilic substitution reaction between cis-2,6-dimethyl piperidine and alkyl/aryl sulfonyl chlorides in the presence of triethylamine. These piperidine sulfonamides were subjected to in vitro AChE enzyme inhibition studies and in vivo antiamnesic study to reverse scopolamine induced memory loss in rats. Two derivatives (3a and f) in this class of piperidines (3a-i) showed considerable inhibition against different sources of ACNE in vitro and reduced average number of mistakes done by wistar rats as compared to scopolamine treated group in vivo (rodent memory evaluation). (C) 2009 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.04.042

文献信息

• Active site directed docking studies: Synthesis and pharmacological evaluation of cis-2,6-dimethyl piperidine sulfonamides as inhibitors of acetylcholinesterase
  作者：H.R. Girisha、J.N. Narendra Sharath Chandra、Sriramamurthy Boppana、Manish Malviya、C.T. Sadashiva、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.ejmech.2009.04.042

  日期：2009.10

  Hypocholinergic function associated with Alzheimer's disease (AD) is well-accepted hypothesis, in this regard, many research attempts have been made to elevate the reduced cholinergic neurotransmission, among them two main treatment strategies were widely explored, namely stimulation of muscarinic receptor 1 and/or reversible inhibition of acetylcholinesterase (AChE) enzyme. In an attempt to improve the efficacy and to minimize general side effects of these ACNE inhibitors, many lead molecules are developed in research; one among them is piperidine derivative. Donazepil is a widely prescribed ACNE inhibitor which displays a piperidine ring in its structure. In the present study, we have docked cis-2,6-dimethyl piperidine sulfonamides (3a-i) on ACNE enzyme and synthesized by nucleophilic substitution reaction between cis-2,6-dimethyl piperidine and alkyl/aryl sulfonyl chlorides in the presence of triethylamine. These piperidine sulfonamides were subjected to in vitro AChE enzyme inhibition studies and in vivo antiamnesic study to reverse scopolamine induced memory loss in rats. Two derivatives (3a and f) in this class of piperidines (3a-i) showed considerable inhibition against different sources of ACNE in vitro and reduced average number of mistakes done by wistar rats as compared to scopolamine treated group in vivo (rodent memory evaluation). (C) 2009 Published by Elsevier Masson SAS.