D-glutamic acid 1,5-didiosgenyl ester | 1414998-82-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: D-glutamic acid 1,5-didiosgenyl ester
• 英文别名: D-Glutamic Acid 1,5-Didiosgenyl Ester；bis[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl] (2R)-2-aminopentanedioate
• CAS: 1414998-82-5
• 化学式: C₅₉H₈₉NO₈
• 分子量: 940.358
• InChiKey: VQIFSTWKHSYFNI-UTVAYBPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  68
• 可旋转键数：
  8
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  D-glutamic acid 1,5-didiosgenyl ester 、 邻乙酰水杨酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以93%的产率得到N-(2-hydroxybenzoyl)-D-glutamic acid 1,5-didiosgenyl ester
  参考文献：
  名称：

  Synthesis, characterization and biological studies of diosgenyl analogues

  摘要：

  A series of optical amino acid diosgenyl esters and diosgenyl salicylate conjugates were designed and synthesized to develop new anticancer and anti-inflammatory agents. The analogue 9c that contains an 6-aminohexanoic acid residue at C-3 of diosgenin exhibits higher potency against all three tumor cell lines with IC50 values ranging from 4.7 mu M in C26 cells to 14.6 mu M in Hep G2 cells. In addition, seven of newly synthesized compounds significantly inhibit xylene-induced ear edema and exhibit comparable or better anti-inflammatory activities than those of diosgenin and aspirin. Furthermore, preliminary structure-activity relationship studies demonstrate that diosgenyl salicylate conjugates have stronger anti-inflammatory activities than amino acid diosgenyl esters. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.086
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-D-glutamic acid 1,5-didiosgenyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以86%的产率得到D-glutamic acid 1,5-didiosgenyl ester
  参考文献：
  名称：

  Synthesis, characterization and biological studies of diosgenyl analogues

  摘要：

  A series of optical amino acid diosgenyl esters and diosgenyl salicylate conjugates were designed and synthesized to develop new anticancer and anti-inflammatory agents. The analogue 9c that contains an 6-aminohexanoic acid residue at C-3 of diosgenin exhibits higher potency against all three tumor cell lines with IC50 values ranging from 4.7 mu M in C26 cells to 14.6 mu M in Hep G2 cells. In addition, seven of newly synthesized compounds significantly inhibit xylene-induced ear edema and exhibit comparable or better anti-inflammatory activities than those of diosgenin and aspirin. Furthermore, preliminary structure-activity relationship studies demonstrate that diosgenyl salicylate conjugates have stronger anti-inflammatory activities than amino acid diosgenyl esters. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.086

文献信息

• Synthesis, characterization and biological studies of diosgenyl analogues
  作者：Baozhan Huang、Dan Du、Rui Zhang、Xiaohua Wu、Zhihua Xing、Yang He、Wen Huang

  DOI：10.1016/j.bmcl.2012.10.086

  日期：2012.12

  A series of optical amino acid diosgenyl esters and diosgenyl salicylate conjugates were designed and synthesized to develop new anticancer and anti-inflammatory agents. The analogue 9c that contains an 6-aminohexanoic acid residue at C-3 of diosgenin exhibits higher potency against all three tumor cell lines with IC50 values ranging from 4.7 mu M in C26 cells to 14.6 mu M in Hep G2 cells. In addition, seven of newly synthesized compounds significantly inhibit xylene-induced ear edema and exhibit comparable or better anti-inflammatory activities than those of diosgenin and aspirin. Furthermore, preliminary structure-activity relationship studies demonstrate that diosgenyl salicylate conjugates have stronger anti-inflammatory activities than amino acid diosgenyl esters. (C) 2012 Elsevier Ltd. All rights reserved.