N-tert-butoxycarbonyl-1,4-dideoxy-2,3-O-isopropylidene-5-O-(p-phenylbenzyl)-1,4-imino-D-ribitol | 1189331-56-3

• 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: N-tert-butoxycarbonyl-1,4-dideoxy-2,3-O-isopropylidene-5-O-(p-phenylbenzyl)-1,4-imino-D-ribitol
• CAS: 1189331-56-3
• 化学式: C₂₆H₃₃NO₅
• 分子量: 439.552
• InChiKey: VGGYYKRDEIZBMD-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-1,4-dideoxy-2,3-O-isopropylidene-5-O-(p-phenylbenzyl)-1,4-imino-D-ribitol 在 三氟乙酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 以56%的产率得到1,4-dideoxy-5-O-(p-phenylbenzyl)-1,4-imino-D-ribitol
  参考文献：
  名称：

  Anti-cancer activity of 5-O-alkyl 1,4-imino-1,4-dideoxyribitols

  摘要：

  New derivatives of 1,4-dideoxy-1,4-imino-D-ribitol have been prepared and evaluated for their cytotoxicity on solid and haematological malignancies. 1,4-Dideoxy-5-O-[(9Z)-octadec-9-en-1-yl]-1,4-imino-Dribitol (13, IC50 similar to 2 mu M) and its C-18-analogues (IC50 < 10 mu M) are cytotoxic toward SKBR3 (breast cancer) cells. 13 also inhibits (IC50 similar to 8 mu M) growth of JURKAT cells. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.07.053
• 作为产物：
  描述：

  N-tert-butyloxycarbonyl-1,4-dideoxy-2,3-O-isopropyliden-1,4-imino-D-allitol 在 sodium tetrahydroborate 、 sodium periodate 、 水 、 四丁基碘化铵 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 生成 N-tert-butoxycarbonyl-1,4-dideoxy-2,3-O-isopropylidene-5-O-(p-phenylbenzyl)-1,4-imino-D-ribitol
  参考文献：
  名称：

  Anti-cancer activity of 5-O-alkyl 1,4-imino-1,4-dideoxyribitols

  摘要：

  New derivatives of 1,4-dideoxy-1,4-imino-D-ribitol have been prepared and evaluated for their cytotoxicity on solid and haematological malignancies. 1,4-Dideoxy-5-O-[(9Z)-octadec-9-en-1-yl]-1,4-imino-Dribitol (13, IC50 similar to 2 mu M) and its C-18-analogues (IC50 < 10 mu M) are cytotoxic toward SKBR3 (breast cancer) cells. 13 also inhibits (IC50 similar to 8 mu M) growth of JURKAT cells. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.07.053