[4-[5-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(E)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-4-hydroxy-6-oxo-1H-pyridin-3-yl]phenyl] 5-aminopentanoate | 1432134-35-4

• 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: [4-[5-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(E)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-4-hydroxy-6-oxo-1H-pyridin-3-yl]phenyl] 5-aminopentanoate
• CAS: 1432134-35-4
• 化学式: C₃₂H₄₀N₂O₅
• 分子量: 532.68
• InChiKey: SJMIFNFZKUPIPJ-RZRQWZGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [4-[5-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(E)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-4-hydroxy-6-oxo-1H-pyridin-3-yl]phenyl] 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 在 三氟乙酸 作用下， 生成 [4-[5-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(E)-prop-1-enyl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-4-hydroxy-6-oxo-1H-pyridin-3-yl]phenyl] 5-aminopentanoate
  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.