7-acetoxymulin-9,12-diene | 1268492-83-6

• 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: 7-acetoxymulin-9,12-diene
• 英文别名: 7β-acetoxymulin-9,12-diene；mulin-9,12-dien-7β-yl acetate；(3R,3aR,5S,5aS)-3a,5a,8-Trimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,5a,6,7,10-decahydrocyclohepta[e]inden-5-yl acetate；[(3R,3aR,5S,5aS)-3a,5a,8-trimethyl-3-propan-2-yl-1,2,3,4,5,6,7,10-octahydrocyclohepta[e]inden-5-yl] acetate
• CAS: 1268492-83-6
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: FTFLXFWZKWKBEX-KDXIVRHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-acetoxymulin-9,12-diene 在 mercury(II) diacetate 、 水 、 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以60%的产率得到
  参考文献：
  名称：

  ANTIMICROBIAL ACTIVITIES OF DITERPENOIDS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA

  摘要：

  The antibacterial activity of two natural diterpenoids isolated from Azorella compacta together with six semisynthetic derivatives, were evaluated against three bacteria: Staphylococcus aureus. Escherichia coli and Mycobacterium smegmatis. The synthesis of the semisynthetic derivatives 3-5 and 8 have not been previously reported with the methods described in this research. The structures of all diterpenoids were elucidated by NMR H-1,C- 13 and IR spectroscopy. The natural diterpenoids, mulinolic acid (1) and azorellanol (2) did not present antibacterial activity, but the six derivatives: 12-oxo-11,13-alpha,alpha-dihydroxymulin-20-oic acid (3), 11-oxo-12,13-alpha,alpha-dihydroxymulin-20-oic acid (4) 11,12-dioxo-13-alpha-hydroxymulin-20-oic acid (5). 7-acetoxymulin-9,12-diene (6). mulin-9,12-dien-7-ol (7) and 7-acetoxy-12,13-dihydroxymulin-9-en (8) were active against three tested bacteria. The antibacterial activity reported for six semisynthetic diterpenoids may not be comparable with positive control ampicillin but demonstrate the possibility of modification of the biological activity of diterpenoids.

  DOI：

  10.4067/s0717-97072018000404200
• 作为产物：
  描述：

  azorellanol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以86.3%的产率得到7-acetoxymulin-9,12-diene
  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