[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(methylamino)-3-oxopropanoate | 1228638-61-6

• 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: [(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(methylamino)-3-oxopropanoate
• CAS: 1228638-61-6
• 化学式: C₃₆H₅₉NO₇
• 分子量: 617.867
• InChiKey: LWPGNARDQPZJQR-ZSIJTDDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  papyriferic acid 、 甲胺 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以46.4%的产率得到[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-(methylamino)-3-oxopropanoate
  参考文献：
  名称：

  Papyriferic acid derivatives as reversal agents of multidrug resistance in cancer cells

  摘要：

  Forty-one derivatives of papyriferic acid were prepared based on our previous finding that methyl papyriferate (3) showed potent reversing effect on cytotoxicity of colchicine against multidrug resistance (MDR) human cancer cells (KB-C2), and evaluated for their cytotoxicity and effect on reversing P-gp-mediated MDR against KB-C2 cells. 3-O-(Morpholino-b-oxopropanoyl)-12 beta-acetoxy-3 alpha,25-dihydroxy-(20S,24R)-epoxydammarane (37) significantly increased the sensitivity of colchicine against KB-C2 cells by 185-fold at 5 mu g/mL (7.4 mu M), and the cytotoxicity of colchicine was recovered to nearly that of sensitive (KB) cells. The other several new amide derivatives also exhibited potent reversal activity comparable to or more potent than methyl papyriferate and verapamil. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.046

文献信息

• Papyriferic acid derivatives as reversal agents of multidrug resistance in cancer cells
  作者：Juan Xiong、Masatoshi Taniguchi、Yoshiki Kashiwada、Michiko Sekiya、Takashi Yamagishi、Yoshihisa Takaishi

  DOI：10.1016/j.bmc.2010.02.046

  日期：2010.4

  Forty-one derivatives of papyriferic acid were prepared based on our previous finding that methyl papyriferate (3) showed potent reversing effect on cytotoxicity of colchicine against multidrug resistance (MDR) human cancer cells (KB-C2), and evaluated for their cytotoxicity and effect on reversing P-gp-mediated MDR against KB-C2 cells. 3-O-(Morpholino-b-oxopropanoyl)-12 beta-acetoxy-3 alpha,25-dihydroxy-(20S,24R)-epoxydammarane (37) significantly increased the sensitivity of colchicine against KB-C2 cells by 185-fold at 5 mu g/mL (7.4 mu M), and the cytotoxicity of colchicine was recovered to nearly that of sensitive (KB) cells. The other several new amide derivatives also exhibited potent reversal activity comparable to or more potent than methyl papyriferate and verapamil. (C) 2010 Elsevier Ltd. All rights reserved.