3-[(7S)-4,7-dimethyl-1-[(E)-prop-1-enyl]-5,6,7,8-tetrahydronaphthalene-2-carbonyl]-4-hydroxy-5-(4-hydroxyphenyl)-1H-pyridin-2-one | 1432134-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[(7S)-4,7-dimethyl-1-[(E)-prop-1-enyl]-5,6,7,8-tetrahydronaphthalene-2-carbonyl]-4-hydroxy-5-(4-hydroxyphenyl)-1H-pyridin-2-one
• CAS: 1432134-66-1
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: YRMKMSSFENGEHH-RGDDUWESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ilicicolin H 在 selenium(IV) oxide 、 甲酸 作用下， 以 氯仿 为溶剂， 以46%的产率得到(1S,10S,11R,12R,14S)-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),5,17-triene-7,9-dione
  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.