(3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl (R)-3-methyl-1-oxo-1-(piperidin-1-ylamino)butan-2-ylcarbamate | 1190921-58-4

• 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: (3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl (R)-3-methyl-1-oxo-1-(piperidin-1-ylamino)butan-2-ylcarbamate
• 英文别名: PPI-2836；[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-[(2R)-3-methyl-1-oxo-1-(piperidin-1-ylamino)butan-2-yl]carbamate
• CAS: 1190921-58-4
• 化学式: C₂₇H₄₅N₃O₆
• 分子量: 507.671
• InChiKey: IYYSKVWXLRFTES-GDJJCEENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R)-2-[[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxycarbonylamino]-3-methylbutanoic acid 、 1-氨基哌啶 生成 (3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl (R)-3-methyl-1-oxo-1-(piperidin-1-ylamino)butan-2-ylcarbamate
  参考文献：
  名称：

  Antiparasitic activities of novel, orally available fumagillin analogs

  摘要：

  Fumagillin, an irreversible inhibitor of MetAP2, has been shown to potently inhibit growth of malaria parasites in vitro. Here, we demonstrate activity of fumagillin analogs with an improved pharmacokinetic profile against malaria parasites, trypanosomes, and amoebas. A subset of the compounds showed efficacy in a murine malaria model. The observed SAR forms a basis for further optimization of fumagillin based inhibitors against parasitic targets by inhibition of MetAP2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.029

文献信息

• Antiparasitic activities of novel, orally available fumagillin analogs
  作者：Christopher Arico-Muendel、Paolo A. Centrella、Brooke D. Contonio、Barry A. Morgan、Gary O’Donovan、Christopher L. Paradise、Steven R. Skinner、Barbara Sluboski、Jennifer L. Svendsen、Kerry F. White、Anjan Debnath、Jiri Gut、Nathan Wilson、James H. McKerrow、Joseph L. DeRisi、Philip J. Rosenthal、Peter K. Chiang

  DOI：10.1016/j.bmcl.2009.07.029

  日期：2009.9

  Fumagillin, an irreversible inhibitor of MetAP2, has been shown to potently inhibit growth of malaria parasites in vitro. Here, we demonstrate activity of fumagillin analogs with an improved pharmacokinetic profile against malaria parasites, trypanosomes, and amoebas. A subset of the compounds showed efficacy in a murine malaria model. The observed SAR forms a basis for further optimization of fumagillin based inhibitors against parasitic targets by inhibition of MetAP2. (C) 2009 Elsevier Ltd. All rights reserved.