methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate | 157240-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate
• 英文别名: methyl (2R,3S)-3-amino-3-(4-fluorophenyl)-2-hydroxypropanoate
• CAS: 157240-38-5
• 化学式: C₁₀H₁₂FNO₃
• 分子量: 213.209
• InChiKey: KIGKIXZTFGVZFM-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate 在 4-二甲氨基吡啶 、 甲酸 、 4-甲基苯磺酸吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 56.0h， 生成 N-de-tert-butoxycarbonyl-N-[2-(1,1-difluoro-2-methyl)propyloxycarbonyl]-7,10-di-(2,2,2-trichloroethyloxycarbonyl)-3-dephenyl-3'-(4-fluorophenyl)docetaxel
  参考文献：
  名称：

  Synthesis, cytotoxicity, metabolic stability and pharmacokinetic evaluation of fluorinated docetaxel analogs

  摘要：

  Three novel fluorinated docetaxel analogs, along with six previous reported, were evaluated for their cytotoxicity against five tumor cell lines. The results indicated that these analogs maintained similar/ more potent activity than docetaxel against these tumor cell lines. They were also evaluated for their metabolic stability and pharmacokinetics, which demonstrated that these analogs showed better profiles of metabolic stability and pharmacokinetics than that of docetaxel. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.027
• 作为产物：
  描述：

  isopropyl (2R,3S)-3-acetylamino-2-hydroxy-3-(4-fluorophenyl)propionate 在 盐酸 、 氯化亚砜 、 水 作用下， 反应 4.0h， 生成 methyl (2R,3S)-3-amino-2-hydroxy-3-(4-fluoro-phenyl)propionate
  参考文献：
  名称：

  Synthesis, cytotoxicity, metabolic stability and pharmacokinetic evaluation of fluorinated docetaxel analogs

  摘要：

  Three novel fluorinated docetaxel analogs, along with six previous reported, were evaluated for their cytotoxicity against five tumor cell lines. The results indicated that these analogs maintained similar/ more potent activity than docetaxel against these tumor cell lines. They were also evaluated for their metabolic stability and pharmacokinetics, which demonstrated that these analogs showed better profiles of metabolic stability and pharmacokinetics than that of docetaxel. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.027

文献信息

• Process for the preparation of .beta.-phenylisoserine and .beta.-lactam
  申请人：Rhone-Poulence Rorer S.A.

  公开号：US05939561A1

  公开（公告）日：1999-08-17

  The present invention relates to new process for the preparation of .beta.-phenylisoserine and its analogues of general formula: ##STR1## which are particularly useful for preparing taxane derivatives which have remarkable antitumour and antileukaemic activities.

  本发明涉及一种新的制备β-苯基异丝氨酸及其类似物的方法，其一般化学式如下：##STR1## 这些化合物特别适用于制备具有显著抗肿瘤和抗白血病活性的紫杉醇衍生物。
• Process for the preparation of .beta.-phenylisoserine and its analogues
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05608102A1

  公开（公告）日：1997-03-04

  This invention relates to a method for preparing .beta.-phenylisoserine and analogues thereof having general formula (I) ##STR1## from an aromatic aldehyde and an .alpha.-methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of general formula (I) (R.dbd.H) may be used to prepare taxane derivatives having remarkable antitumoral and antileukaemic activity.

  这项发明涉及一种制备β-苯基异丝氨酸及其类似物的方法，其通式为(I)。从芳香醛和α-甲基芳基胺-S，以及本文所述的通式(II)的内酰胺中制备。通式(I)中的酸(R=H)可用于制备具有显著抗肿瘤和抗白血病活性的紫杉醇衍生物。
• A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs
  作者：Jean Dominique Bourzat、Alain Commerçon

  DOI：10.1016/s0040-4039(00)61724-0

  日期：1993.9

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).
• Synthesis, cytotoxicity, metabolic stability and pharmacokinetic evaluation of fluorinated docetaxel analogs
  作者：Hong-Fu Lu、Cheng Xie、Jun Chang、Guo-Qiang Lin、Xun Sun

  DOI：10.1016/j.ejmech.2011.02.027

  日期：2011.5

  Three novel fluorinated docetaxel analogs, along with six previous reported, were evaluated for their cytotoxicity against five tumor cell lines. The results indicated that these analogs maintained similar/ more potent activity than docetaxel against these tumor cell lines. They were also evaluated for their metabolic stability and pharmacokinetics, which demonstrated that these analogs showed better profiles of metabolic stability and pharmacokinetics than that of docetaxel. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.