3,19-(3'-nitrobenzylidene)andrographolide | 908130-79-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,19-(3'-nitrobenzylidene)andrographolide
• 英文别名: (3E,4S)-3-[2-[(4aR,6aS,7R,10aS,10bR)-Decahydro-6a,10b-dimethyl-8-methylene-3-(3-nitrophenyl)-1H-naphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone；(3E,4S)-3-[2-[(4aR,6aS,7R,10aS,10bR)-6a,10b-dimethyl-8-methylidene-3-(3-nitrophenyl)-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-4-hydroxyoxolan-2-one
• CAS: 908130-79-0
• 化学式: C₂₇H₃₃NO₇
• 分子量: 483.562
• InChiKey: HVBCJBLBYPKWDH-OPDNHIMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 穿心莲内酯 在 Amberlyst-15 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以64%的产率得到3,19-(3'-nitrobenzylidene)andrographolide
  参考文献：
  名称：

  Anti-HIV activity of semisynthetic derivatives of andrographolide and computational study of HIV-1 gp120 protein binding

  摘要：

  Andrographolide, a diterpene lactone of the Andrographis paniculata, displays anti-HIV activity in vitro. A series of andrographolide derivatives have been synthesized and evaluated for their anti-HIV activity in a cell-free virus infectivity assay using TZM-bl cells. As compared to andrographolide, 3-nitrobenzylidene derivative 6 showed higher in vitro anti-HIV activity, whereas 2',6'-dichloro-nicotinoyl ester derivative 9 showed higher Therapeutic Index. The andrographolide and its derivatives, 6 and 9, inhibited gp120-mediated cell fusion of HL2/3 cells (expressing gp120 on its surface) with TZM-bl cells (expressing CD4 and co-receptors CCR5 & CXCR4). Further, computational studies revealed that these molecules bind to the important residues of V3 loop of gp120. These results suggest that andrographolide derivatives may be promising candidates for prevention of HIV infection. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.030

文献信息

• Anti-HIV activity of semisynthetic derivatives of andrographolide and computational study of HIV-1 gp120 protein binding
  作者：Mayur M. Uttekar、Tiyasa Das、Rohan S. Pawar、Beena Bhandari、Vidya Menon、Nutan、Satish K. Gupta、Sujata V. Bhat

  DOI：10.1016/j.ejmech.2012.07.030

  日期：2012.10

  Andrographolide, a diterpene lactone of the Andrographis paniculata, displays anti-HIV activity in vitro. A series of andrographolide derivatives have been synthesized and evaluated for their anti-HIV activity in a cell-free virus infectivity assay using TZM-bl cells. As compared to andrographolide, 3-nitrobenzylidene derivative 6 showed higher in vitro anti-HIV activity, whereas 2',6'-dichloro-nicotinoyl ester derivative 9 showed higher Therapeutic Index. The andrographolide and its derivatives, 6 and 9, inhibited gp120-mediated cell fusion of HL2/3 cells (expressing gp120 on its surface) with TZM-bl cells (expressing CD4 and co-receptors CCR5 & CXCR4). Further, computational studies revealed that these molecules bind to the important residues of V3 loop of gp120. These results suggest that andrographolide derivatives may be promising candidates for prevention of HIV infection. (C) 2012 Elsevier Masson SAS. All rights reserved.