3-nor-2,4-secofriedelan-4-oxo-2-oic acid | 113376-11-7

• 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: 3-nor-2,4-secofriedelan-4-oxo-2-oic acid
• 英文别名: 4-oxo-3,4-seco-A(1)-norfriedelan-3-oic acid；4-oxa-3,4-secofriedelan-3-oic acid；norfriedonic acid；Norfriedonsaeure；((4aS)-2t.4bt.6at.9.9.10bc.12at-Heptamethyl-2c-acetyl-(4arH.19atH)-octadecahydro-chrysenyl-(1t))-essigsaeure；3-Oxo-2.3-seco-A-nor-friedelansaeure-(2)；4-Oxo-2.3-seco-23-nor-friedelansaeure-(2)；2-[(1S,2S,4aS,4bR,6aR,10aR,10bS,12aR)-2-acetyl-2,4b,6a,9,9,10b,12a-heptamethyl-1,3,4,4a,5,6,7,8,10,10a,11,12-dodecahydrochrysen-1-yl]acetic acid
• CAS: 113376-11-7
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: PBRRQRYVRNSVBF-BCNFPARNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-nor-2,4-secofriedelan-4-oxo-2-oic acid 在 lead(IV) tetraacetate 、 溶剂黄146 作用下， 反应 4.0h， 以68%的产率得到2,3:3,4-diseco-3-norfriedelan-4-ol-2-oic lactone
  参考文献：
  名称：

  Synthesis of friedelan triterpenoid analogs with DNA topoisomerase IIα inhibitory activity and their molecular docking studies

  摘要：

  Five highly oxygenated friedelan derivatives (3a, 3b, 4, 5a and 5b) were synthesized. The structures of these compounds were established on the basis of spectral (IR, 1D and 2D NMR, MS etc.) and chemical data. The molecules, including the parent compounds were screened for three-dimensional (3D) molecular docking on the crystal structure of topoisomerase II alpha (1 bgw for topoisomerase II alpha PDB). Compounds 3a and 5a showed a dose dependent inhibition of catalytic activity of human topoisomerase II alpha. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.037
• 作为产物：
  描述：

  A-nor-friedelene-(2) 在 potassium permanganate 、 溶剂黄146 作用下， 生成 3-nor-2,4-secofriedelan-4-oxo-2-oic acid
  参考文献：
  名称：

  Drake; Wolfe, Journal of the American Chemical Society, 1939, vol. 61, p. 3076

  摘要：

  DOI：

文献信息

• Basic Autoxidation of Friedelin
  作者：Tadaaki Nishihama、Takeyoshi Takahashi

  DOI：10.1246/bcsj.60.2117

  日期：1987.6

  Base-catalyzed autoxidation of a triterpene ketone, friedelin, in the presence of potassium t-butoxide gave four products, and their structures and formation mechanism were investigated. The common intermediate to these compounds was suggested to be 4-hydroperoxyfriedelan-3-one, not friedelane-2,3-dione. 3-Oxafriedel-1-ene-2-carboxylic acid was a dehydration product of the main product, 2-hydroxy-

  在叔丁醇钾的存在下碱催化三萜酮弗里德林自氧化得到四种产物，并研究了它们的结构和形成机制。这些化合物的常见中间体被认为是 4-hydroperoxyfriedelan-3-one，而不是 Friedelane-2,3-dione。3-Oxafriedel-1-ene-2-羧酸是主要产物2-羟基-3-oxafriedelane-2-羧酸的脱水产物。
• Hemisynthetic Secofriedelane Triterpenes with Inhibitory Activity against the Growth of Human Tumor Cell Lines in Vitro
  作者：Cristina Moiteiro、César Manta、Fátima Justino、Regina Tavares、Maria João M. Curto、Madalena Pedro、Maria São José Nascimento、Madalena Pinto

  DOI：10.1021/np0498915

  日期：2004.7.1

  Seco acids 7 and 9 and hydroxylated analogues 5 and 6 derived from friedelane triterpenes were synthesized stereoselectively in high yields. Compounds 5-9 were evaluated for their ability to inhibit in vitro the growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer). Only compounds 7 and 9 were found to possess significant growth inhibitory effects, exhibiting GI(50) values that range from 24.6 to 32.8 muM and 10.9 to 17.6 muM, respectively.