Δ(2,3)-(4S)-ivermectin ethyl secoester | 1135339-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Δ(2,3)-(4S)-ivermectin ethyl secoester
• 英文别名: delta2,3-(4S)-Ivermectin ethyl secoester；ethyl (3E,3aR,6S,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-6H-1-benzofuran-4-carboxylate
• CAS: 1135339-50-2
• 化学式: C₅₀H₈₀O₁₅
• 分子量: 921.176
• InChiKey: CSXUBIJQYABUCP-HGHVTTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 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

• 作为反应物：
  描述：

  Δ(2,3)-(4S)-ivermectin ethyl secoester 在 臭氧 、 solvent red 19 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 、 甲醇 为溶剂， 以58%的产率得到
  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
• 作为产物：
  描述：

  titanium(IV) tetraethanolate 、 Δ(2,3)-(4S)-ivermectin 以 乙醇 为溶剂， 反应 120.0h， 以53%的产率得到Δ(2,3)-(4S)-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

• 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.