combretastatin D-4 | 126191-24-0

• 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: combretastatin D-4
• 英文别名: Corniculatolide A；4-hydroxy-2,11-dioxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),15,18-hexaen-10-one
• CAS: 126191-24-0
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: GTGFVTOGSQUFFF-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：

  combretastatin D-4 、 乙酸酐 在 吡啶 作用下， 以2 mg的产率得到11-acetoxycorniculatolide 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：

  (3R,4S)-(-)-combretastatin D-1 生成 combretastatin D-4
  参考文献：
  名称：

  SINGH, SHEO BUX;PETTIT, GEORGE R., J. ORG. CHEM., 55,(1990) N, C. 2797-2800

  摘要：

  DOI：

文献信息

• Antineoplastic Agents. 565. Synthesis of Combretastatin D-2 Phosphate and Dihydro-combretastatin D-2
  作者：George R. Pettit、Peter D. Quistorf、Jeremy A. Fry、Delbert L. Herald、Ernest Hamel、Jean-Charles Chapuis

  DOI：10.1021/np800635h

  日期：2009.5.22

  A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25−28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether

  设计了一种改良的考布他汀 D-2 ( 5 )合成路线，以进一步评估其生物活性，将其转化为磷酸盐前药 ( 25 - 28 )，并作为获得二氢考布他汀 D-2 ( 42 )的途径. 从饱和的 3-苯基丙酸酯中间体开始，通过 Ullmann 联芳醚反应 ( 39 - 41 ) ，完成了二氢考布他汀 D-2 的平行第一次全合成。与考布他汀 D-2 表现出的癌细胞生长抑制活性相反，相对较小的结构修饰 ( 41 , 42 ) 导致这些特性的消除。
• Syntheses of Combretastatins D-1, D-2, and D-4 via Ring Contraction by Flash Vacuum Pyrolysis
  作者：Marina Harras、Wolfgang Milius、R. Alan Aitken、Rainer Schobert

  DOI：10.1021/acs.joc.6b02586

  日期：2017.1.6

  combretastatins D-2 and D-4 as well as a formal synthesis of combretastatin D-1 by a conceptually new route harnessing a ring-contracting flash vacuum pyrolytic extrusion of sulfur dioxide from the respective 16-membered sulfone precursors. Via flash vacuum pyrolysis, even metaparacyclophanes as small and strained as the hitherto unknown oxa[1.5]metaparacyclophane could be prepared as a side product en

  我们报告了康布雷他汀D-2和D-4的合成，以及康布雷他汀D-1的正式合成，其方法是利用从相应的16元砜前体中环氧化的快速真空热解法挤出二氧化硫的概念新方法。通过快速真空热解，甚至可以通过同步挤出SO 2和CO 2，制备出与迄今未知的oxa [1.5] metaparaparaphanphane一样小且应变过大的metaparacyclophanes作为副产物，以通向combretastatin D- 2。
• Synthesis and Antitumor Activity of Combretastatin D-4
  作者：Shigeru Nishiyama、Kanako Uno、Takamasa Tanabe、Takahisa Ogamino、Ryoko Okada、Masaya Imoto

  DOI：10.3987/com-07-11221

  日期：——
• Antineoplastic agents. 206. Structure of the cytostatic macrocyclic lactone combretastatin D-2
  作者：Sheo Bux Singh、George R. Pettit

  DOI：10.1021/jo00296a043

  日期：1990.4
• 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).