14,15-deoxyhavanensin triacetate | 30317-23-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 14,15-deoxyhavanensin triacetate
• 英文别名: 1,3,7-tri-O-acetyl-14,15-deoxyhavanensin；[(1S,3R,5S,7R,8R,9R,10S,13S,17R)-1,3-diacetyloxy-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-7-yl] acetate
• CAS: 30317-23-8
• 化学式: C₃₂H₄₄O₇
• 分子量: 540.697
• InChiKey: JFZWEEGAFRZPEY-TXQBVQDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  14,15-deoxyhavanensin triacetate 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以33%的产率得到1α,3α,7α-triacetoxy-21β-hydroxy-24,25,26,27-tetranor-apotirucalla-14,20(22)-dien-23,21-olide
  参考文献：
  名称：

  15 种柠檬苦素的 1 H 和 13 C NMR 谱的完整归属

  摘要：

  介绍了 15 种柠檬苦素的 1H 和 13C NMR 化学位移的明确和完整的分配，其中 8 种在天然来源中发现，另外 7 种是其他合成衍生物。分配基于 2D 位移相关 [1H,1H-CO​​SY, 1H,13C-gHSQC-1J(C,H), 1H,13C-gHMBC-nJ(C,H) (n = 2 and 3)] 和NOE 实验。版权所有 © 2003 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.1159
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 14,15-deoxyhavanensin triacetate
  参考文献：
  名称：

  Biological investigation and structure–activity relationship studies on azadirone from Azadirachta indica A. Juss

  摘要：

  Azadirone 1, a limonoidal constituent of Azadirachta indica is found to possess potent cytotoxic activity against a panel of human cancer cell lines in our in vitro studies. In vitro screening of a number of semi-synthetic analogues of 1 revealed that the a,p-unsaturated enone moiety or its equivalent conjugated system in A-ring, C-7 acetyloxy/chloroacetyloxy or keto group in B-ring and the furan moiety are responsible for the activity of 1 and its analogues. Compound I and two of the semi-synthetic analogues 10 and 13 were found to possess good in vivo antitumor activity in modified hollow fiber animal models. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.030

文献信息

• Limonoids from Trichilia havanensis
  作者：Carlos Arenas、Lydia Rodriguez-Hahn

  DOI：10.1016/0031-9422(90)87113-9

  日期：1990.1

  Abstract The limonoids of the seeds of Trichilia havanensis were studied in two ripening stages. From the unripened seeds azadirone, havanensin triacetate and three new limonoids were isolated. The mature seeds contained havanesin triacetate and its hydroxy lactone derivative. The structures of the new limonoids were deduced by spectroscopic and chemical means.

  摘要 在两个成熟阶段研究了Trichilia havanensis 种子的柠檬苦素类化合物。从未成熟的种子中分离出氮杂二酮、三醋酸哈瓦那菌素和三种新的柠檬苦素。成熟种子含有havanesin三乙酸酯及其羟基内酯衍生物。新的柠檬苦素的结构是通过光谱和化学方法推导出来的。
• Biological investigation and structure–activity relationship studies on azadirone from Azadirachta indica A. Juss
  作者：Srinivas Nanduri、Siva Sanjeeva Rao Thunuguntla、Vijay Kumar Nyavanandi、Sridevi Kasu、P.Mahesh Kumar、P.Sai Ram、Sriram Rajagopal、R.Ajaya Kumar、Dhanvanthri S Deevi、R Rajagopalan、A Venkateswarlu

  DOI：10.1016/j.bmcl.2003.08.030

  日期：2003.11

  Azadirone 1, a limonoidal constituent of Azadirachta indica is found to possess potent cytotoxic activity against a panel of human cancer cell lines in our in vitro studies. In vitro screening of a number of semi-synthetic analogues of 1 revealed that the a,p-unsaturated enone moiety or its equivalent conjugated system in A-ring, C-7 acetyloxy/chloroacetyloxy or keto group in B-ring and the furan moiety are responsible for the activity of 1 and its analogues. Compound I and two of the semi-synthetic analogues 10 and 13 were found to possess good in vivo antitumor activity in modified hollow fiber animal models. (C) 2003 Elsevier Ltd. All rights reserved.
• Complete assignments of the¹H and¹³C NMR spectra of 15 limonoids
  作者：Benjamín Rodríguez

  DOI：10.1002/mrc.1159

  日期：2003.3

  Unambiguous and complete assignments of 1H and 13C NMR chemical shifts for 15 limonoids, eight of them found in natural sources and seven other synthetic derivatives, are presented. The assignments are based on 2D shift‐correlated [1H,1H‐COSY, 1H,13C‐gHSQC‐1J(C,H), 1H,13C‐gHMBC‐nJ(C,H) (n = 2 and 3)] and NOE experiments. Copyright © 2003 John Wiley & Sons, Ltd.

  介绍了 15 种柠檬苦素的 1H 和 13C NMR 化学位移的明确和完整的分配，其中 8 种在天然来源中发现，另外 7 种是其他合成衍生物。分配基于 2D 位移相关 [1H,1H-CO​​SY, 1H,13C-gHSQC-1J(C,H), 1H,13C-gHMBC-nJ(C,H) (n = 2 and 3)] 和NOE 实验。版权所有 © 2003 John Wiley & Sons, Ltd.