5H-Naphtho[2a(2),3a(2):5,6]pyrano[2,3-b]pyridin-5-one, 5a,6,6a,7,8,9,10,10a,11,11a-decahydro-4,11-dihydroxy-3-(4-hydroxyphenyl)-8,11-dimethyl-6-(1-propenyl)-, [5aS-[5aI+/-,6I+/-(E),6aI+/-,8I(2),10aI(2),11I+/-,11aI+/-]]- | 71376-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5H-Naphtho[2a(2),3a(2):5,6]pyrano[2,3-b]pyridin-5-one, 5a,6,6a,7,8,9,10,10a,11,11a-decahydro-4,11-dihydroxy-3-(4-hydroxyphenyl)-8,11-dimethyl-6-(1-propenyl)-, [5aS-[5aI+/-,6I+/-(E),6aI+/-,8I(2),10aI(2),11I+/-,11aI+/-]]-
• 英文别名: (1S,10S,11R,12R,14S,17S,18S)-18-hydroxy-6-(4-hydroxyphenyl)-14,18-dimethyl-11-[(E)-prop-1-enyl]-2-oxa-4-azatetracyclo[8.8.0.03,8.012,17]octadeca-3(8),5-diene-7,9-dione
• CAS: 71376-29-9
• 化学式: C₂₇H₃₁NO₅
• 分子量: 449.547
• InChiKey: AZVKJAHCTJYSCC-IBLBDXNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ilicicolin H 在 间氯过氧苯甲酸 作用下， 以4%的产率得到3-[(1R,2R,4aS,7S,8aS)-4,7-dimethyl-1-(3-methyloxiran-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-4-hydroxy-5-(4-hydroxyphenyl)-1H-pyridin-2-one
  参考文献：
  名称：

  Structure–activity relationship of cytochrome bc1 reductase inhibitor broad spectrum antifungal ilicicolin H

  摘要：

  Ilicicolin H is a broad spectrum antifungal agent showing sub micro g/mL MICs against Candida spp., Aspergillus fumigatus and Cryptococcus spp. It is a potent inhibitor (C-50 2-3 ng/mL) of the mitochondrial cytochrome bc1 reductase with over 1000-fold selectivity against rat liver cytochrome bc1 reductase. Structure-activity relationship of semisynthetic derivatives by chemical modification of ilicicolin H and its 19-hydroxy derivative produced by biotransformation have been described. Basic 4'-esters and moderately polar N- and O-alkyl derivatives retained antifungal and the cytochrome bc1 reductase activities. 4',19-Diacetate and 19-cyclopropyl acetate retained antifungal and enzyme activity and selectivity with over 20-fold improvement of plasma protein binding. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.023

文献信息

• Structure–activity relationship of cytochrome bc1 reductase inhibitor broad spectrum antifungal ilicicolin H
  作者：Sheo B. Singh、Weiguo Liu、Xiaohua Li、Tom Chen、Ali Shafiee、Sarah Dreikorn、Viktor Hornak、Maria Meinz、Janet C. Onishi

  DOI：10.1016/j.bmcl.2013.03.023

  日期：2013.5

  Ilicicolin H is a broad spectrum antifungal agent showing sub micro g/mL MICs against Candida spp., Aspergillus fumigatus and Cryptococcus spp. It is a potent inhibitor (C-50 2-3 ng/mL) of the mitochondrial cytochrome bc1 reductase with over 1000-fold selectivity against rat liver cytochrome bc1 reductase. Structure-activity relationship of semisynthetic derivatives by chemical modification of ilicicolin H and its 19-hydroxy derivative produced by biotransformation have been described. Basic 4'-esters and moderately polar N- and O-alkyl derivatives retained antifungal and the cytochrome bc1 reductase activities. 4',19-Diacetate and 19-cyclopropyl acetate retained antifungal and enzyme activity and selectivity with over 20-fold improvement of plasma protein binding. (C) 2013 Elsevier Ltd. All rights reserved.