(3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-30-ethyl-27-(2-hydroxyethylsulfanyl)-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone | 108466-76-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-30-ethyl-27-(2-hydroxyethylsulfanyl)-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• 英文别名: (3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-30-ethyl-27-(2-hydroxyethylsulfanyl)-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• CAS: 108466-76-8
• 化学式: C₆₄H₁₁₅N₁₁O₁₃S
• 分子量: 1278.75
• InChiKey: LIFRUTHXRYPBGV-HJWUMUHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  89
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  324
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-30-ethyl-27-(2-hydroxyethylsulfanyl)-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone 在 Sebekia benihana 、 水 作用下， 以 乙醇 为溶剂， 以5%的产率得到(3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-30-ethyl-27-(2-hydroxyethylsulfanyl)-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-24-(2-hydroxy-2-methyl-propyl)-6,9,18-triisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
  参考文献：
  名称：

  Synthesis of non-immunosuppressive cyclophilin-Binding cyclosporin A derivatives as potential anti-HIV-1 drugs

  摘要：

  Original cyclosporin A (CsA) derivatives bearing various alkylthio side chains at the sarcosine residue 3 (R configuration) and for the most potent and selective compounds a 4'-hydroxyl group at the Me-Leucine residue 4 were prepared in one or two steps from commercially available CsA. The [2-(dimethyl or diethylamino)-ethylthio-Sar](3)-[(4'-OH)MeLeu](4)-CsA derivatives 3k and 3l displayed potent in vitro anti-HIV-1 (IC50 similar to 46 nM) and low immunosuppressive activities (IC50 > 1500 nM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.042
• 作为产物：
  描述：

  cyclosporin A 在 sodium amide 、 三氟乙酸 作用下， 以 四氢呋喃 、 氨 为溶剂， 反应 4.0h， 生成 (3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-30-ethyl-27-(2-hydroxyethylsulfanyl)-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
  参考文献：
  名称：

  Synthesis of non-immunosuppressive cyclophilin-Binding cyclosporin A derivatives as potential anti-HIV-1 drugs

  摘要：

  Original cyclosporin A (CsA) derivatives bearing various alkylthio side chains at the sarcosine residue 3 (R configuration) and for the most potent and selective compounds a 4'-hydroxyl group at the Me-Leucine residue 4 were prepared in one or two steps from commercially available CsA. The [2-(dimethyl or diethylamino)-ethylthio-Sar](3)-[(4'-OH)MeLeu](4)-CsA derivatives 3k and 3l displayed potent in vitro anti-HIV-1 (IC50 similar to 46 nM) and low immunosuppressive activities (IC50 > 1500 nM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.042

文献信息

• Synthesis of non-immunosuppressive cyclophilin-Binding cyclosporin A derivatives as potential anti-HIV-1 drugs
  作者：Michel Evers、Jean-Claude Barrière、Georges Bashiardes、Anne Bousseau、Jean-Christophe Carry、Norbert Dereu、Bruno Filoche、Yvette Henin、Serge Sablé、Marc Vuilhorgne、Serge Mignani

  DOI：10.1016/j.bmcl.2003.09.042

  日期：2003.12

  Original cyclosporin A (CsA) derivatives bearing various alkylthio side chains at the sarcosine residue 3 (R configuration) and for the most potent and selective compounds a 4'-hydroxyl group at the Me-Leucine residue 4 were prepared in one or two steps from commercially available CsA. The [2-(dimethyl or diethylamino)-ethylthio-Sar](3)-[(4'-OH)MeLeu](4)-CsA derivatives 3k and 3l displayed potent in vitro anti-HIV-1 (IC50 similar to 46 nM) and low immunosuppressive activities (IC50 > 1500 nM). (C) 2003 Elsevier Ltd. All rights reserved.