methyl (2S)-2-[methyl-[(2S)-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl(oct-7-enoyl)amino]butanoyl]amino]butanoyl]amino]butanoyl]amino]propanoyl]amino]-3-phenylpropanoate | 1227747-09-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[methyl-[(2S)-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl(oct-7-enoyl)amino]butanoyl]amino]butanoyl]amino]butanoyl]amino]propanoyl]amino]-3-phenylpropanoate
• CAS: 1227747-09-2
• 化学式: C₄₁H₆₇N₅O₇
• 分子量: 742.012
• InChiKey: HBOCJYXOBUCRBG-ZQUIBHIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  53
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S)-2-[methyl-[(2S)-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl(oct-7-enoyl)amino]butanoyl]amino]butanoyl]amino]butanoyl]amino]propanoyl]amino]-3-phenylpropanoic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 苯 为溶剂， 反应 12.0h， 以56%的产率得到methyl (2S)-2-[methyl-[(2S)-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl(oct-7-enoyl)amino]butanoyl]amino]butanoyl]amino]butanoyl]amino]propanoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  Almiramides A−C: Discovery and Development of a New Class of Leishmaniasis Lead Compounds

  摘要：

  Leishmaniasis is a debilitating disease caused by protozoan parasites of the genus Leishmania, which affects an estimated 12 million people worldwide. The discovery of new lead compounds for leishmaniasis is therefore a pressing concern for global health programs. The organic extract of a Panamanian collection of the marine cyanobacterium Lyngbya majuscula showed strong in vitro activity in two complementary screens against the tropical parasite Leishmania donovani, the causative agent of visceral leishmaniasis. Chromatographic separation of this complex mixture led to the isolation of the highly N-methylated linear lipopeptides, almiramides A-C (1-3). Comparison with the biological activities of a number of related metabolites and semisynthetic derivatives revealed key features required for activity and afforded one new compound (11) with superior in vitro activity. Subsequent synthesis of a library of simplified analogues led to the discovery of several compounds with improved therapeutic indices to the natural products.

  DOI：

  10.1021/jm100265s

文献信息

• Almiramides A−C: Discovery and Development of a New Class of Leishmaniasis Lead Compounds
  作者：Laura M. Sanchez、Dioxelis Lopez、Brian A. Vesely、Gina Della Togna、William H. Gerwick、Dennis E. Kyle、Roger G. Linington

  DOI：10.1021/jm100265s

  日期：2010.5.27

  Leishmaniasis is a debilitating disease caused by protozoan parasites of the genus Leishmania, which affects an estimated 12 million people worldwide. The discovery of new lead compounds for leishmaniasis is therefore a pressing concern for global health programs. The organic extract of a Panamanian collection of the marine cyanobacterium Lyngbya majuscula showed strong in vitro activity in two complementary screens against the tropical parasite Leishmania donovani, the causative agent of visceral leishmaniasis. Chromatographic separation of this complex mixture led to the isolation of the highly N-methylated linear lipopeptides, almiramides A-C (1-3). Comparison with the biological activities of a number of related metabolites and semisynthetic derivatives revealed key features required for activity and afforded one new compound (11) with superior in vitro activity. Subsequent synthesis of a library of simplified analogues led to the discovery of several compounds with improved therapeutic indices to the natural products.