(2S)-2-(3,4-dichlorophenyl)-N-(dimethylsulfamoyl)-N-methyl-4-(1-oxospiro[2H-1-benzothiophene-3,4'-piperidine]-1'-yl)butan-1-amine

• 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: (2S)-2-(3,4-dichlorophenyl)-N-(dimethylsulfamoyl)-N-methyl-4-(1-oxospiro[2H-1-benzothiophene-3,4'-piperidine]-1'-yl)butan-1-amine
• 化学式: C₂₅H₃₃Cl₂N₃O₃S₂
• 分子量: 558.593
• InChiKey: AXMFPMPIDBXVKP-DKVUXROGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-2-(3,4-二氯苯基)戊-4-烯酸N-甲基酰胺 在 盐酸 、 Oxone 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 丙酮 、 叔丁醇 为溶剂， 反应 0.08h， 生成 (2S)-2-(3,4-dichlorophenyl)-N-(dimethylsulfamoyl)-N-methyl-4-(1-oxospiro[2H-1-benzothiophene-3,4'-piperidine]-1'-yl)butan-1-amine
  参考文献：
  名称：

  Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 1: Discovery and initial structure–activity relationships for 1-amino-2-phenyl-4-(piperidin-1-yl)butanes

  摘要：

  Screening of the Merck sample collection for compounds with CCR5 receptor binding afforded (2S)-2-(3,4-dichlorophenyl)- 1-[N-(methyl)-N-(phenylsulfonyl)amino]-4,4'-piperidin-1'-yl)]butane S-oxide (4) as a potent lead structure having an IC50 binding affinity of 35 nM. Herein, we describe the discovery of this lead structure and our initial structure-activity relationship studies directed toward the requirement for and optimization of the 1-amino fragment. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00637-5

文献信息

• Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 1: Discovery and initial structure–activity relationships for 1-amino-2-phenyl-4-(piperidin-1-yl)butanes
  作者：Conrad P. Dorn、Paul E. Finke、Bryan Oates、Richard J. Budhu、Sander G. Mills、Malcolm MacCoss、Lorraine Malkowitz、Martin S. Springer、Bruce L. Daugherty、Sandra L. Gould、Julie A. DeMartino、Salvatore J. Siciliano、Anthony Carella、Gwen Carver、Karen Holmes、Renee Danzeisen、Daria Hazuda、Joseph Kessler、Janet Lineberger、Michael Miller、William A. Schleif、Emilio A. Emini

  DOI：10.1016/s0960-894x(00)00637-5

  日期：2001.1

  Screening of the Merck sample collection for compounds with CCR5 receptor binding afforded (2S)-2-(3,4-dichlorophenyl)- 1-[N-(methyl)-N-(phenylsulfonyl)amino]-4,4'-piperidin-1'-yl)]butane S-oxide (4) as a potent lead structure having an IC50 binding affinity of 35 nM. Herein, we describe the discovery of this lead structure and our initial structure-activity relationship studies directed toward the requirement for and optimization of the 1-amino fragment. (C) 2001 Published by Elsevier Science Ltd.