methyl 4-phenyl-D-phenylglycinate

• 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 4-phenyl-D-phenylglycinate
• 英文别名: methyl (2R)-2-amino-2-(4-phenylphenyl)acetate
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: DXSRQHCLOHVMKH-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-phenyl-D-phenylglycinate 在 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 (2S,3R,4S)-N-tert-butoxycarbonyl-2-{{{(1R)-2-hydroxy-1-[[1,1’-biphenyl]-4-l]ethyl}amino}ethyl}-3,4-O-isopropylidenepyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis of Pyrrolidine 3,4-Diol Derivatives with Anticancer Activity on Pancreatic Tumor Cells

  摘要：

  Novel pyrrolidine 3,4-diol derivatives of the type (2R and 2S,3R,45){[(( 1R)-1-methoxycarbonyl and hydroxylmethyl)-1-arylmethyl)amino] ethyl}-pyrrolidine-3,4-diol have been prepared and evaluated as a-mannosidase inhibitors and assayed for their anticancer activity in vitro. They all exhibit specific but moderate activity as inhibitors towards a-mannosidase from Jack beans. Compounds 7 and 8b bearing hydroxymethyl and trifluoromethylbiphenyl groups show the best antiproliferative effect in two pancreatic cancer cell lines.

  DOI：

  10.3987/com-13-s(s)111
• 作为产物：
  描述：

  4-氨基乙基联苯 在 盐酸 、 仲丁基锂 、 三乙胺 、 鹰爪豆碱 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 6.33h， 生成 methyl 4-phenyl-D-phenylglycinate
  参考文献：
  名称：

  通过苄基锂化反应快速获得N- Boc苯基甘氨酸衍生物

  摘要：

  我们报告了一种新型有效的方法，用于N- Boc保护的苯基甘氨酸的对映选择性合成。产率和对映体比率根据溶剂，底物的性质和形成手性络合物的方法而有很大差异。结果表明，主要反应途径是对映选择性去质子化/取代过程。对映选择性似乎受s -BuLi-（-）-天冬氨酸络合物的手性鉴别能力的限制。所述的合成方法是获得有用的对映体富集的N- Boc苯基甘氨酸衍生物的最短途径之一。

  DOI：

  10.1016/s0040-4020(01)00159-4

文献信息

• Derivatives of Dihydroxypyrrolidine as Anti-Cancer Compounds
  申请人：EPFL Ecole Polytechnique Fédérale de Lausanne

  公开号：EP2067771A1

  公开（公告）日：2009-06-10

  The present invention relates to derivatives of dihydroxypyrrolidine useful in the treatment of cancer. The invention further relates to a process for making the compounds. The compounds are inhibitors of α mannosidase, and possibly, also inhibit nicotinamide phosphoribosyl transferase.

  本发明涉及一种二羟基吡咯烷衍生物，可用于癌症治疗。该发明还涉及一种制备该化合物的方法。该化合物是α甘露糖苷酶的抑制剂，可能也抑制烟酰胺磷酸核糖转移酶。
• Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies
  作者：Claudia Bello、Michele Cea、Giovanna Dal Bello、Anna Garuti、Ilaria Rocco、Gabriella Cirmena、Eva Moran、Aimable Nahimana、Michel A. Duchosal、Floriana Fruscione、Paolo Pronzato、Francesco Grossi、Franco Patrone、Alberto Ballestrero、Marc Dupuis、Bernard Sordat、Alessio Nencioni、Pierre Vogel

  DOI：10.1016/j.bmc.2010.03.009

  日期：2010.5

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-([(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.
• Rapid access to N -Boc phenylglycine derivatives via benzylic lithiation reactions
  作者：Claude Barberis、Normand Voyer、Johanne Roby、Sylvain Chénard、Martin Tremblay、Philippe Labrie

  DOI：10.1016/s0040-4020(01)00159-4

  日期：2001.4

  novel and efficient method for the enantioselective synthesis of N-Boc protected phenylglycines. Yields and enantiomeric ratios vary widely depending on the nature of the solvent, the substrate and on the method of forming the chiral complex. Results show that the major reaction pathway is an enantioselective deprotonation/substitution process. The enantioselectivity appears to be limited by the chiral

  我们报告了一种新型有效的方法，用于N- Boc保护的苯基甘氨酸的对映选择性合成。产率和对映体比率根据溶剂，底物的性质和形成手性络合物的方法而有很大差异。结果表明，主要反应途径是对映选择性去质子化/取代过程。对映选择性似乎受s -BuLi-（-）-天冬氨酸络合物的手性鉴别能力的限制。所述的合成方法是获得有用的对映体富集的N- Boc苯基甘氨酸衍生物的最短途径之一。
• Synthesis of Pyrrolidine 3,4-Diol Derivatives with Anticancer Activity on Pancreatic Tumor Cells
  作者：Inmaculada Robina、Frederic Steimer、Ana T. Carmona、Antonio J. Moreno-Vargas、Irene Caffa、Fabrizio Montecucco、Alessio Nencioni、Pierre Vogel

  DOI：10.3987/com-13-s(s)111

  日期：——

  Novel pyrrolidine 3,4-diol derivatives of the type (2R and 2S,3R,45)[(( 1R)-1-methoxycarbonyl and hydroxylmethyl)-1-arylmethyl)amino] ethyl}-pyrrolidine-3,4-diol have been prepared and evaluated as a-mannosidase inhibitors and assayed for their anticancer activity in vitro. They all exhibit specific but moderate activity as inhibitors towards a-mannosidase from Jack beans. Compounds 7 and 8b bearing hydroxymethyl and trifluoromethylbiphenyl groups show the best antiproliferative effect in two pancreatic cancer cell lines.