4-{(S)-4-[(S)-1-(4-Benzo[1,3]dioxol-5-ylmethyl-phenyl)-ethyl]-3-methyl-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester | 376392-81-3

• 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: 4-{(S)-4-[(S)-1-(4-Benzo[1,3]dioxol-5-ylmethyl-phenyl)-ethyl]-3-methyl-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-[(3S)-4-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]piperidine-1-carboxylate
• CAS: 376392-81-3
• 化学式: C₃₁H₄₃N₃O₄
• 分子量: 521.7
• InChiKey: IFRIBOUIUGFGPA-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54.48
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-{(S)-4-[(S)-1-(4-Benzo[1,3]dioxol-5-ylmethyl-phenyl)-ethyl]-3-methyl-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 生成 (2S)-1-[(1S)-1-[4-(1,3-benzodioxol-5-ylmethyl)phenyl]ethyl]-2-methyl-4-piperidin-4-ylpiperazine
  参考文献：
  名称：

  Piperazine-Based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element

  摘要：

  Optimization of the piperidino-piperazines 1 and 2 provided early leads 3 and 4, which showed good activity in the CCR5-RANTES binding assay and in antiviral assays. A systematic study around these structures showed that the 2(S)-methyl piperazine is essential for CCR5 affinity, which is further enhanced by forming the 2,6-dimethyl benzamide of the piperidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00381-x
• 作为产物：
  描述：

  N-{(S)-1-[4-(Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-phenyl]-ethyl}-2,2,2-trifluoro-acetamide 在 三乙基硅烷 、 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氨 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-{(S)-4-[(S)-1-(4-Benzo[1,3]dioxol-5-ylmethyl-phenyl)-ethyl]-3-methyl-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Piperazine-Based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element

  摘要：

  Optimization of the piperidino-piperazines 1 and 2 provided early leads 3 and 4, which showed good activity in the CCR5-RANTES binding assay and in antiviral assays. A systematic study around these structures showed that the 2(S)-methyl piperazine is essential for CCR5 affinity, which is further enhanced by forming the 2,6-dimethyl benzamide of the piperidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00381-x

文献信息

• Piperazine-Based CCR5 antagonists as HIV-1 inhibitors. I: 2(S)-methyl piperazine as a key pharmacophore element
  作者：Jayaram R. Tagat、Stuart W. McCombie、Ruo W. Steensma、Sue-Ing Lin、Dennis V. Nazareno、Bahige Baroudy、Nicole Vantuno、Serena Xu、Jia Liu

  DOI：10.1016/s0960-894x(01)00381-x

  日期：2001.8

  Optimization of the piperidino-piperazines 1 and 2 provided early leads 3 and 4, which showed good activity in the CCR5-RANTES binding assay and in antiviral assays. A systematic study around these structures showed that the 2(S)-methyl piperazine is essential for CCR5 affinity, which is further enhanced by forming the 2,6-dimethyl benzamide of the piperidine. (C) 2001 Elsevier Science Ltd. All rights reserved.