(20R)-3β-O-(boc-L-alanyl)dammarane-12β,20,25-triol | 1421035-47-3

• 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: (20R)-3β-O-(boc-L-alanyl)dammarane-12β,20,25-triol
• 英文别名: [(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-12-hydroxy-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] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1421035-47-3
• 化学式: C₃₈H₆₇NO₇
• 分子量: 649.952
• InChiKey: XPWOTEZVBDTBTC-WTZOPYSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (20R)-3β-O-(boc-L-alanyl)dammarane-12β,20,25-triol 在 silica gel 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以73%的产率得到(20R)-3β-O-(L-alanyl)dammarane-12β,20,25-triol
  参考文献：
  名称：

  Semi-synthesis and anti-tumor evaluation of novel 25-hydroxyprotopanaxadiol derivatives as apoptosis inducing agents

  摘要：

  在25-OH-PPD衍生物中，化合物3xt和9xt表现出最强的抗肿瘤活性，并显着诱导DU145细胞凋亡。

  DOI：

  10.1039/c5md00382b
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 25(R)-羟基原人参二醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以11%的产率得到(20R)-12β-O-(boc-L-alanyl)dammarane-3β,20,25-triol
  参考文献：
  名称：

  Synthesis and anti-tumor evaluation of novel 25-hydroxyprotopanaxadiol analogs incorporating natural amino acids

  摘要：

  In the current study, derivatives of 25-hydroxyprotopanaxadiol (25-OH-PPD) were prepared and their in vitro anti-tumor activities were tested on six different human tumor cell lines by standard MET assay. The results showed that combining an ester group combined with the presence of an amino acid moiety led to a 10-fold improved anti-tumor activity. Compound 1c exhibited the best anti-tumor activity in the in vitro assays. Compounds 2c, 3c, 4c, 5c, 6c and 8b showed better anti-tumor activities compared to the parent compound 25-OH-PPD. The current results may provide useful data for researching and developing new anti-cancer agents. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.012

文献信息

• Synthesis and anti-tumor evaluation of novel 25-hydroxyprotopanaxadiol analogs incorporating natural amino acids
  作者：Peng Wang、Xiu-Li Bi、Jing Xu、Hao-Nan Yuan、Hu-Ri Piao、Yu-Qing Zhao

  DOI：10.1016/j.steroids.2012.09.012

  日期：2013.2

  In the current study, derivatives of 25-hydroxyprotopanaxadiol (25-OH-PPD) were prepared and their in vitro anti-tumor activities were tested on six different human tumor cell lines by standard MET assay. The results showed that combining an ester group combined with the presence of an amino acid moiety led to a 10-fold improved anti-tumor activity. Compound 1c exhibited the best anti-tumor activity in the in vitro assays. Compounds 2c, 3c, 4c, 5c, 6c and 8b showed better anti-tumor activities compared to the parent compound 25-OH-PPD. The current results may provide useful data for researching and developing new anti-cancer agents. (C) 2012 Elsevier Inc. All rights reserved.
• Semi-synthesis and anti-tumor evaluation of novel 25-hydroxyprotopanaxadiol derivatives as apoptosis inducing agents
  作者：Fanzhi Qu、Chen Zhao、Yafei Liu、Jiaqing Cao、Wei Li、Yuqing Zhao

  DOI：10.1039/c5md00382b

  日期：——

  Among novel 25-OH-PPD derivatives, compounds 3xt and 9xt exhibited the most potent anti-tumor activities and significantly induced DU145 cell apoptosis.

  在25-OH-PPD衍生物中，化合物3xt和9xt表现出最强的抗肿瘤活性，并显着诱导DU145细胞凋亡。