(4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid | 191276-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid
• 英文别名: N-benzoyl (4S,5R)-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid；(4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolinecarboxylic acid；(4S,5R)-3-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid
• CAS: 191276-32-1
• 化学式: C₂₅H₂₃NO₆
• 分子量: 433.461
• InChiKey: QTVLOARBZSPHIU-JCVDRHSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.5h， 生成 10-deacetoxy-13,14ene-13-deoxy-13-(N-benzoyl-3-phenylisoserinyl)-carbonylamino baccatin III
  参考文献：
  名称：

  Menichincheri, Maria; Ceccarelli, Walter; Fusar-Bassini, Domenico, Medicinal Chemistry Research, 1996, vol. 6, # 4, p. 264 - 292

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-(4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylate 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以100%的产率得到(4S,5R)-N-benzoyl-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid
  参考文献：
  名称：

  Menichincheri, Maria; Ceccarelli, Walter; Fusar-Bassini, Domenico, Medicinal Chemistry Research, 1996, vol. 6, # 4, p. 264 - 292

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of C-seco paclitaxel analogues
  作者：Giovanni Appendino、Bruno Danieli、Jasmin Jakupovic、Emanuela Belloro、Giovanni Scambia、Ezio Bombardelli

  DOI：10.1016/s0040-4039(97)00877-0

  日期：1997.6

  Starting from 7,9-diTes-10-dehydro C-secobaccatin III (4a), C-seco analogues of paclitaxel retaining biological activity were synthesised. (C) 1997 Elsevier Science Ltd.
• Synthesis of paclitaxel (docetaxel) / 2-deacetoxytaxinine J dimers
  作者：Giovanni Appendino、Emanuela Belloro、Sven Jakupovic、Bruno Danieli、Jasmin Jakupovic、Ezio Bombardelli

  DOI：10.1016/s0040-4020(99)00290-2

  日期：1999.5

  Starting from taxanes available in multigram amounts from widespread ornamental yews (10-deacetylbaccatin III (4) and 2'-deacetoxyaustrospicatine (5)), two dimeric taxoids (3a, 3b) with potential dual target specificity (beta-tubulin and P-gp) were synthesised. Both compounds lacked significant cytotoxicity, though 3b retained a strong activity in the tubulin depolimerisation assay. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and Evaluation of 14-Nor-A-secotaxoids
  作者：Giovanni Appendino、Emanuela Belloro、Erika Del Grosso、Alberto Minassi、Ezio Bombardelli

  DOI：10.1002/1099-0690(20021)2002:2<277::aid-ejoc277>3.0.co;2-f

  日期：2002.1

  A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14beta-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged analogues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-nor-A-secotaxoids warrant further investigation as simplified taxol mimics.
• 12,13-Isobaccatin III. Taxane Enol Esters (12,13-Isotaxanes)
  作者：Robert C. Kelly、Nancy A. Wicnienski、Ilse Gebhard、Samuel J. Qualls、Fusen Han、Paul J. Dobrowolski、Eldon G. Nidy、Roy A. Johnson

  DOI：10.1021/ja953702a

  日期：1996.1.1
• US5556878A
  申请人：——

  公开号：US5556878A

  公开（公告）日：1996-09-17