17-acetoxymulinic acid | 131917-12-9

• 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: 17-acetoxymulinic acid
• 英文别名: (1R,2S,3S,6R,7S,10R,12R)-10-(acetyloxymethyl)-16-methyl-6-propan-2-yl-13,14-dioxatetracyclo[10.2.2.02,10.03,7]hexadec-15-ene-7-carboxylic acid
• CAS: 131917-12-9
• 化学式: C₂₂H₃₂O₆
• 分子量: 392.492
• InChiKey: RDNDSRLZDOEQBR-VSONCLMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 17-acetoxymulinic acid 以 乙醚 为溶剂， 反应 2.0h， 以92.5%的产率得到17-acetoxy-mulinic acid methyl ester
  参考文献：
  名称：

  Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids

  摘要：

  The antituberculosis activity of 14 natural azorellane and mulinane diterpenoids isolated from Azorella compacta, Azorella madreporica, Mulinum crassifolium, and Laretia acaulis, together with eight semisynthetic derivatives, was evaluated against two Mycobacterium tuberculosis strains. The natural azorellanes azorellanol (3) and 17-acetoxy-13-alpha-hydroxyazorellane (6), and the semisynthetic mulinanes 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13) and mulinenic acid methyl ester (23), showed the strongest activity, with MIC values of 12.5 mu g/mL against both strains. The methylated derivatives 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13), mulin-11,13-dien-20-oic acid methyl ester (15) and mulinenic acid methyl ester (23) proved to be more active than the parent compounds. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2009.07.005

文献信息

• Antituberculosis activity of alkylated mulinane diterpenoids
  作者：Gloria María Molina-Salinas、Jorge Bórquez、Salvador Said-Fernández、Luis Alberto Loyola、Alejandro Yam-Puc、Pola Becerril-Montes、Fabiola Escalante-Erosa、Luis Manuel Peña-Rodríguez

  DOI：10.1016/j.fitote.2009.09.006

  日期：2010.4

  Natural azorellane and mulinane diterpenoids show antituberculosis activity, which is increased by methylation of their free carboxyl group. We have systematically investigated the effect of alkylation in this class of diterpenoids and found that the profile of bioactivity is relatively unaffected by the introduction of short alkyl groups, both linear and branched In this investigation. three semisynthetic diterpenoids, 13 hydroxy-mulin-11-en-20-oic acid n-propyl ester (3) and the n-propyl (19) and n-butyl (20) esters of isomulinic acid, showed the strongest antituberculosis activity (MIC = 6 25 mu g/mL) against a drug-resistant strain of Mycobacterium tuberculosis (C) 2009 Elsevier B V. All rights reserved
• Antituberculosis activity of natural and semisynthetic azorellane and mulinane diterpenoids
  作者：Gloria María Molina-Salinas、Jorge Bórquez、Alejandro Ardiles、Salvador Said-Fernández、Luis Alberto Loyola、Aurelio San-Martín、Isidro González-Collado、Luis Manuel Peña-Rodríguez

  DOI：10.1016/j.fitote.2009.07.005

  日期：2010.1

  The antituberculosis activity of 14 natural azorellane and mulinane diterpenoids isolated from Azorella compacta, Azorella madreporica, Mulinum crassifolium, and Laretia acaulis, together with eight semisynthetic derivatives, was evaluated against two Mycobacterium tuberculosis strains. The natural azorellanes azorellanol (3) and 17-acetoxy-13-alpha-hydroxyazorellane (6), and the semisynthetic mulinanes 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13) and mulinenic acid methyl ester (23), showed the strongest activity, with MIC values of 12.5 mu g/mL against both strains. The methylated derivatives 13-hydroxy-mulin-11-en-20-oic-acid methyl ester (13), mulin-11,13-dien-20-oic acid methyl ester (15) and mulinenic acid methyl ester (23) proved to be more active than the parent compounds. (C) 2009 Elsevier B.V. All rights reserved.