Δ(2,3)-(4S)-ivermectin | 1135339-49-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: Δ(2,3)-(4S)-ivermectin
• 英文别名: 2,3-Dehydro-3,4-dihydro ivermectin；(4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,22S,24R)-6'-[(2S)-butan-2-yl]-21,24-dihydroxy-12-[(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-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-1(23),10,14,16-tetraene-6,2'-oxane]-2-one
• CAS: 1135339-49-9
• 化学式: C₄₈H₇₄O₁₄
• 分子量: 875.107
• InChiKey: AZSRBVAPBFWEGT-UQJGBDTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  伊维菌素 B1a 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以89%的产率得到Δ(2,3)-(4S)-ivermectin
  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.