2,3-[N-(4-methylbenzenesulfonyl)imino]-2-phenylpropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

• 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: 2,3-[N-(4-methylbenzenesulfonyl)imino]-2-phenylpropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
• 英文别名: 2-[[(2S,4aR,6R,7R,8S,8aS)-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxymethyl]-1-(4-methylphenyl)sulfonyl-2-phenylaziridine
• 化学式: C₄₃H₄₃NO₈S
• 分子量: 733.882
• InChiKey: WAJDGDILJPNDRL-VTTREVFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-phenylallyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside 、 chloramine T trihydrate 在 phenyltrimethylammonium tribromide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以70%的产率得到2,3-[N-(4-methylbenzenesulfonyl)imino]-2-phenylpropyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity

  摘要：

  A series of new aziridines beta-D-galactopyranoside derivatives were synthesized from alkenyl beta-D-galactopyranosides employing Sharpless conditions. The structures of the compounds were established by H-1 NMR, C-13 NMR, MS, HRMS and elemental analysis. The stereoselectivity of the reaction and the structural requirements of the alkenyl precursor for improving diastereoisomeric excesses of the direct aziridination reaction were also studied.The new compounds were subjected to a preliminary screening for cytotoxic activity against human lung cancer cells vs. human non-malignant lung cells. Terminal aziridine derivatives showed activity and, most notably, selectivity. One of the most active and selective compounds was also evaluated against breast cancer cells, melanoma cells, and non-malignant cells from the same origin. Its cytotoxic activity was similar to that of the positive controls, displaying a highly selective cytotoxic activity against both types of cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.020

文献信息

• Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity
  作者：José M. Vega-Pérez、Carlos Palo-Nieto、Margarita Vega-Holm、Purificación Góngora-Vargas、José Manuel Calderón-Montaño、Estefanía Burgos-Morón、Miguel López-Lázaro、Fernando Iglesias-Guerra

  DOI：10.1016/j.ejmech.2013.10.020

  日期：2013.12

  A series of new aziridines beta-D-galactopyranoside derivatives were synthesized from alkenyl beta-D-galactopyranosides employing Sharpless conditions. The structures of the compounds were established by H-1 NMR, C-13 NMR, MS, HRMS and elemental analysis. The stereoselectivity of the reaction and the structural requirements of the alkenyl precursor for improving diastereoisomeric excesses of the direct aziridination reaction were also studied.The new compounds were subjected to a preliminary screening for cytotoxic activity against human lung cancer cells vs. human non-malignant lung cells. Terminal aziridine derivatives showed activity and, most notably, selectivity. One of the most active and selective compounds was also evaluated against breast cancer cells, melanoma cells, and non-malignant cells from the same origin. Its cytotoxic activity was similar to that of the positive controls, displaying a highly selective cytotoxic activity against both types of cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.