methyl (2S)-2-[[(2S)-1-[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoate | 1309982-05-5

• 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: methyl (2S)-2-[[(2S)-1-[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoate
• CAS: 1309982-05-5
• 化学式: C₄₁H₆₆N₂O₆S
• 分子量: 715.051
• InChiKey: QAFUFFNNYSSBEU-OEKZHVAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2S)-1-[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以80%的产率得到(2S)-2-[[(2S)-1-[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoic acid
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives

  摘要：

  Based on structural modifications of the natural 23-hydroxybetulinic acid, a series of novel its derivatives had been synthesized. The new compounds were screened for in vitro antiproliferative activity against cancer cell lines HeLa, MCF-7, HepG2. B16 and A375 using doxorubicin as a reference. The vast majority of derivatives had exhibited potent tumor growth inhibitory activity than original compound. The derivatives 4, 5, 7, 20, 23, 26, 43 and 44 with IC50 values lower than 10 mu M on all tested cell lines were regarded as the most promising compounds. The structure activity relationships of 23-hydroxybetulinic acid derivatives were also discussed in the present investigations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.038
• 作为产物：
  描述：

  23-hydroxybetulinic acid 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 methyl (2S)-2-[[(2S)-1-[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives

  摘要：

  Based on structural modifications of the natural 23-hydroxybetulinic acid, a series of novel its derivatives had been synthesized. The new compounds were screened for in vitro antiproliferative activity against cancer cell lines HeLa, MCF-7, HepG2. B16 and A375 using doxorubicin as a reference. The vast majority of derivatives had exhibited potent tumor growth inhibitory activity than original compound. The derivatives 4, 5, 7, 20, 23, 26, 43 and 44 with IC50 values lower than 10 mu M on all tested cell lines were regarded as the most promising compounds. The structure activity relationships of 23-hydroxybetulinic acid derivatives were also discussed in the present investigations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.038

文献信息

• Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives
  作者：Ping Lan、Jiao Wang、Dong-Mei Zhang、Chang Shu、Hui-Hui Cao、Ping-Hua Sun、Xiao-Ming Wu、Wen-Cai Ye、Wei-Min Chen

  DOI：10.1016/j.ejmech.2011.03.038

  日期：2011.6

  Based on structural modifications of the natural 23-hydroxybetulinic acid, a series of novel its derivatives had been synthesized. The new compounds were screened for in vitro antiproliferative activity against cancer cell lines HeLa, MCF-7, HepG2. B16 and A375 using doxorubicin as a reference. The vast majority of derivatives had exhibited potent tumor growth inhibitory activity than original compound. The derivatives 4, 5, 7, 20, 23, 26, 43 and 44 with IC50 values lower than 10 mu M on all tested cell lines were regarded as the most promising compounds. The structure activity relationships of 23-hydroxybetulinic acid derivatives were also discussed in the present investigations. (C) 2011 Elsevier Masson SAS. All rights reserved.