(4S,5R)-3-Acetyl-2,2-dimethyl-4-phenyl-oxazolidine-5-carboxylic acid | 607394-06-9

• 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)-3-Acetyl-2,2-dimethyl-4-phenyl-oxazolidine-5-carboxylic acid
• 英文别名: (4S,5R)-3-acetyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid
• CAS: 607394-06-9
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: XZIBOOYFSOPHHK-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-2',3'-O-isopropylideneguanosine 、 (4S,5R)-3-Acetyl-2,2-dimethyl-4-phenyl-oxazolidine-5-carboxylic acid 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 甲苯 、 氯仿 为溶剂， 反应 3.5h， 以39%的产率得到(4S,5R)-3-Acetyl-2,2-dimethyl-4-phenyl-oxazolidine-5-carboxylic acid (3aR,4R,6R,6aR)-6-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  The design and synthesis of guanosine compounds with in vitro activity against the colon cancer cell line SW480: non-Taxane derived mimics of taxol?

  摘要：

  In the course of our investigation into the use of taxol as a lead compound to design new molecules with anti-cancer activity, we have synthesized four compounds based on protected guanosine coupled to taxol isoserine side-chain analogues. These analogues show in vitro anti-cancer activity against the colon cancer cell line SW480 that their constituent parts do not. (C) 2063 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00543-2
• 作为产物：
  描述：

  (E)-isopropyl cinnamate 在 lithium hydroxide 、 Hydroquinone 1,4-phthalazinediyl diether 、 对甲苯磺酸 作用下， 反应 0.33h， 生成 (4S,5R)-3-Acetyl-2,2-dimethyl-4-phenyl-oxazolidine-5-carboxylic acid
  参考文献：
  名称：

  The design and synthesis of guanosine compounds with in vitro activity against the colon cancer cell line SW480: non-Taxane derived mimics of taxol?

  摘要：

  In the course of our investigation into the use of taxol as a lead compound to design new molecules with anti-cancer activity, we have synthesized four compounds based on protected guanosine coupled to taxol isoserine side-chain analogues. These analogues show in vitro anti-cancer activity against the colon cancer cell line SW480 that their constituent parts do not. (C) 2063 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00543-2

文献信息

• The design and synthesis of guanosine compounds with in vitro activity against the colon cancer cell line SW480: non-Taxane derived mimics of taxol?
  作者：Joshua Howarth、Padraic Kenny、Susan McDonnell、Aine O'Connor

  DOI：10.1016/s0960-894x(03)00543-2

  日期：2003.8

  In the course of our investigation into the use of taxol as a lead compound to design new molecules with anti-cancer activity, we have synthesized four compounds based on protected guanosine coupled to taxol isoserine side-chain analogues. These analogues show in vitro anti-cancer activity against the colon cancer cell line SW480 that their constituent parts do not. (C) 2063 Elsevier Ltd. All rights reserved.