isocorniculatolide A | 1360058-54-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: isocorniculatolide A
• 英文别名: isocorniculatolide；4-hydroxy-2,11-dioxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),15,18-hexaen-12-one
• CAS: 1360058-54-3
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: JQXBHAOCMVWRCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isocorniculatolide A 、 乙酸酐 在 吡啶 作用下， 以2 mg的产率得到11-acetoxyisocorniculatolide A
  参考文献：
  名称：

  Unusual Isomeric Corniculatolides from Mangrove, Aegiceras corniculatum

  摘要：

  Four new isomeric macrolides of combretastatin D-2 congeners named isocorniculatolide A (1), 11-O-methylisocorniculatolide A (2), 11-O-methylcomiculatolide A (3), and 12-hydroxy-11-O-methylcorniculatolide A (4), and the known corniculatolide A (5), arjunolic acid, and maslinic acid were isolated from the CHCl3 extract of the bark of Aegiceras corniculatum. The structures of the new compounds (1-4) were elucidated by a combination of spectroscopic analysis (1-5), chemical modifications, and single-crystal X-ray analysis (1).

  DOI：

  10.1021/np200789s
• 作为产物：
  描述：

  3-羟基-4-甲氧基-苯丙醇 在 aluminum (III) chloride 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 19.0h， 生成 isocorniculatolide A
  参考文献：
  名称：

  Synthesis of isomeric corniculatolides

  摘要：

  Synthesis of three natural macrolides 11-O-methylcorniculatolide A, 11-O-methylisocorniculatolide A and isocorniculatolide A is reported using a simple, straight forward and high-yielding route. The present synthesis confirms the assigned molecular structures and provides an access to sufficient quantities of the natural products for the biological evaluation. In addition, we have determined the anti-TB potential of the three natural compounds using Alamar-Blue assay (H(37)Rv) and found no significant inhibitory activity at 100 mu g/ml. Excellent yields, short sequence and useful SAR information are the highlights of the present work. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.010

文献信息

• Unusual Isomeric Corniculatolides from Mangrove, <i>Aegiceras corniculatum</i>
  作者：M. Gowri Ponnapalli、S. CH. V. A. Rao Annam、Saidulu Ravirala、Sushma Sukki、Madhu Ankireddy、V. Raju Tuniki

  DOI：10.1021/np200789s

  日期：2012.2.24

  Four new isomeric macrolides of combretastatin D-2 congeners named isocorniculatolide A (1), 11-O-methylisocorniculatolide A (2), 11-O-methylcomiculatolide A (3), and 12-hydroxy-11-O-methylcorniculatolide A (4), and the known corniculatolide A (5), arjunolic acid, and maslinic acid were isolated from the CHCl3 extract of the bark of Aegiceras corniculatum. The structures of the new compounds (1-4) were elucidated by a combination of spectroscopic analysis (1-5), chemical modifications, and single-crystal X-ray analysis (1).
• Synthesis of isomeric corniculatolides
  作者：Gajanan N. Raut、Kasturi Chakraborty、Priyanka Verma、Rajesh S. Gokhale、D. Srinivasa Reddy

  DOI：10.1016/j.tetlet.2012.09.010

  日期：2012.11

  Synthesis of three natural macrolides 11-O-methylcorniculatolide A, 11-O-methylisocorniculatolide A and isocorniculatolide A is reported using a simple, straight forward and high-yielding route. The present synthesis confirms the assigned molecular structures and provides an access to sufficient quantities of the natural products for the biological evaluation. In addition, we have determined the anti-TB potential of the three natural compounds using Alamar-Blue assay (H(37)Rv) and found no significant inhibitory activity at 100 mu g/ml. Excellent yields, short sequence and useful SAR information are the highlights of the present work. (C) 2012 Elsevier Ltd. All rights reserved.