ivermectin ethyl secoester | 865775-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ivermectin ethyl secoester
• 英文别名: ethyl (3E,3aS,4R,7R,7aR)-3-[(2E,4S,5S,6E)-8-[(2R,3S,6R,8R,10S)-2-[(2S)-butan-2-yl]-10-hydroxy-3-methyl-1,7-dioxaspiro[5.5]undecan-8-yl]-5-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethylocta-2,6-dienylidene]-3a,7-dihydroxy-6-methyl-7,7a-dihydro-4H-1-benzofuran-4-carboxylate
• CAS: 865775-57-1
• 化学式: C₅₀H₈₀O₁₅
• 分子量: 921.176
• InChiKey: HROFXLXSDUCNMC-GHTKYWHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  65
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  190
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  titanium(IV) tetraethanolate 、 伊维菌素 B1a 以 乙醇 为溶剂， 以68%的产率得到ivermectin ethyl secoester
  参考文献：
  名称：

  Ivermectin-derived leishmanicidal compounds

  摘要：

  In the present study a family of macrocyclic and acyclic analogues as well as seco-analogues of avermectins were prepared from commercial Ivermectin (IVM) and their antileishmanial activity assayed against axenic promastigote and intracellular amastigote forms of Leishmania amazonensis. Contrarily to the filaricidal activity, the leishmanicidal potentiality of avermectin analogues does not appear to depend on the integrity of the non-conjugated Delta(3,4)- hexahydrobenzofuran moiety. Conjugated Delta(2,3)- IVM or its corresponding conjugated secoester show higher anti-leishmania activity than the parent compound. Surprisingly, the diglycosylated northern sub-unit exhibits the same anti-amastigote potentiality as the southern hexahydrobenzofuran. As expected for compounds derived from the widely used Ivermectin antibiotic, little toxicity has been noticed for most of the novel analogues prepared. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.003

文献信息

• Preparation of Intact Hexahydrobenzofuran Subunits of Ivermectin by Selective Ozonolysis of the Δ3,4-Intermediate Secoester
  作者：Anderson Rouge dos Santos、Maria de Lourdes Garcia Ferreira、Carlos R. Kaiser、Jean-Pierre Férézou

  DOI：10.1002/ejoc.200500033

  日期：2005.8

  profile, we decided to develop a practical synthetic strategy starting from southern subunits cut from commercial Ivermectin, which is now easily available at a reasonable price. We describe here the first process for preparing intact hexahydrobenzofuran subunits by controlled degradation of Ivermectin in a basically three-step process that totally preserves the integrity of the Δ3 unsaturated pattern

  阿维菌素，尤其是其半合成的部分氢化加合物伊维菌素，构成了世界范围内兽医使用的有效杀虫剂家族，该家族已为人所知 20 多年，并且在治疗各种人类丝虫病方面也表现出极大的功效。在一个设计具有新的或优化的医学特征的具有成本效益的类似物的新途径的计划中，我们决定开发一种实用的合成策略，从从商业伊维菌素切割的南部亚基开始，现在可以以合理的价格轻松获得。我们在这里描述了第一个通过控制伊维菌素降解制备完整六氢苯并呋喃亚基的过程，该过程基本上分为三步，完全保留了单元的 Δ3 不饱和模式的完整性，这是该分子家族生物活性的必要特征。该序列的两个关键步骤是在克级规模上开发的，涉及在钛 (IV) 醇盐存在下的酯交换反应，该反应允许大环内酯开环而没有异构化，产率为 55-70%，然后是 C10 的选择性臭氧分解-C11 双键在不同还原剂的存在下以合理的产率提供预期的南方单元。(© Wiley-VCH Verlag GmbH
• Ivermectin-derived leishmanicidal compounds
  作者：Anderson Rouge dos Santos、Camila Alves Bandeira Falcão、Michelle Frazão Muzitano、Carlos Roland Kaiser、Bartira Rossi-Bergmann、Jean-Pierre Férézou

  DOI：10.1016/j.bmc.2008.12.003

  日期：2009.1

  In the present study a family of macrocyclic and acyclic analogues as well as seco-analogues of avermectins were prepared from commercial Ivermectin (IVM) and their antileishmanial activity assayed against axenic promastigote and intracellular amastigote forms of Leishmania amazonensis. Contrarily to the filaricidal activity, the leishmanicidal potentiality of avermectin analogues does not appear to depend on the integrity of the non-conjugated Delta(3,4)- hexahydrobenzofuran moiety. Conjugated Delta(2,3)- IVM or its corresponding conjugated secoester show higher anti-leishmania activity than the parent compound. Surprisingly, the diglycosylated northern sub-unit exhibits the same anti-amastigote potentiality as the southern hexahydrobenzofuran. As expected for compounds derived from the widely used Ivermectin antibiotic, little toxicity has been noticed for most of the novel analogues prepared. (C) 2008 Elsevier Ltd. All rights reserved.