methyl (S)-2-amino-2-(biphenyl-4-yl)acetate

• 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 (S)-2-amino-2-(biphenyl-4-yl)acetate
• 英文别名: methyl (2S)-2-amino-2-(4-phenylphenyl)acetate
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: DXSRQHCLOHVMKH-AWEZNQCLSA-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 (S)-2-amino-2-(biphenyl-4-yl)acetate 在 盐酸 、 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 (2S,3R,4S)-2-{{{(1S)-2-hydroxy-1-[[1,1’-biphenyl]-4-yl]ethyl}amino}ethyl}pyrolidine-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

文献信息

• Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[<i>d</i>]sultams
  作者：Francesca Foschi、Aaron Tagliabue、Voichita Mihali、Tullio Pilati、Ilir Pecnikaj、Michele Penso

  DOI：10.1021/ol401557v

  日期：2013.7.19

  The "memory of chirality" stereodivergent synthesis of polyfluorobenzo[d]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions.
• 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.