3,19-isopropylideneandrographolide-8,17-α-epoxide | 774581-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,19-isopropylideneandrographolide-8,17-α-epoxide
• 英文别名: 8,17-epoxy-3,19-O-isopropylidene-andrographolide
• CAS: 774581-29-2
• 化学式: C₂₃H₃₄O₆
• 分子量: 406.519
• InChiKey: CMDWEXHDIPBFKK-SOWDXHDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  77.52
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,19-isopropylideneandrographolide-8,17-α-epoxide 在 氯甲酸乙酯 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (S,E)-4-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl 3-(benzo[d][1,3]dioxol-5-yl)acrylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090
• 作为产物：
  描述：

  穿心莲内酯 在 4-甲基苯磺酸吡啶 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 二甲基亚砜 、 苯 为溶剂， 反应 14.0h， 生成 3,19-isopropylideneandrographolide-8,17-α-epoxide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090

文献信息

• Stereoselective Synthesis and Biological Evaluation of <i>ent</i> -Asperolide C and its Analogues
  作者：Zhengyuan Xin、Yunlong Lu Zhiqiang Song、Yuchen He、Jiabin Li、Kejiang Lin、Xiaowen Xue

  DOI：10.1002/ejoc.201701292

  日期：2018.1.31

  The first synthesis of ent‐asperolide C and its analogues is described, along with an evaluation of their cytotoxicity. ent‐Asperolide C was synthesized in 10 steps from the naturally occurring diterpenoid andrographolide, with asymmetric epoxidation of the exocyclic double bond, and tandem oxidative cleavage of the C‐14=C‐15 double bond and subsequent epoxide ring opening as the key steps.

  介绍了对头孢菌素C及其类似物的首次合成，以及对它们的细胞毒性的评估。ENT -Asperolide下在选自天然存在的二萜类化合物的穿心莲内酯的10个步骤合成，用环外双键的不对称环氧化，而C-14 = C-15双键的串联氧化裂解和随后的环氧化物开环的关键步骤。
• Synthesis and biological evaluation of andrographolide analogues as anti-cancer agents
  作者：Ranjan Preet、Biswajit Chakraborty、Sumit Siddharth、Purusottam Mohapatra、Dipon Das、Shakti Ranjan Satapathy、Supriya Das、Nakul C. Maiti、Prakas R. Maulik、Chanakya Nath Kundu、Chinmay Chowdhury

  DOI：10.1016/j.ejmech.2014.07.088

  日期：2014.10

  A new family of andrographolide analogues were synthesized and screened in vitro against kidney (HEK-293) and breast (MCF-7) cancer cells. The anti-cancer effects of the active analogues (2b, 2c and 4c) were determined by multiple cell based assays such as MTT, immunostaining, FACS, western blotting and transcriptional inhibition of NF-kappa B activity. Importantly, these compounds were found to possess higher anti-cancer potency than andrographolide and low toxicity to normal (VERO and MCF-10A) cells. Increased level of Bax/Bcl-xL ratio, caspase 3, and sub C1 population, higher expression level of tumor suppressor protein p53 and lower expression level of NF-kappa B suggested potent apoptotic property of the active analogues. Data revealed that the andrographolide derivative-mediated cell death in cancer cells was p53 dependent (C) 2014 Elsevier Masson SAS. All rights reserved.