[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a-carbonochloridoyl-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]chrysen-8-yl]methyl acetate | 916139-48-5

• 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: [(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a-carbonochloridoyl-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]chrysen-8-yl]methyl acetate
• CAS: 916139-48-5
• 化学式: C₃₄H₅₁ClO₅
• 分子量: 575.229
• InChiKey: USJJVJYEMBNTFA-DAKVPFIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a-carbonochloridoyl-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]chrysen-8-yl]methyl acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 23-hydroxy-N,N-diallyl-betulinic amide
  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 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 [(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a-carbonochloridoyl-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]chrysen-8-yl]methyl acetate
  参考文献：
  名称：

  作为抗肿瘤剂候选物的 23-羟基桦木酸 C-28 酯衍生物的合成和生物活性

  摘要：

  23-羟基桦木酸 (1) 作为合成 C-28 酯衍生物的前体。在体外评估了目标化合物对五种细胞系（A549、BEL-7402、SF-763、B16 和 HL-60）的抗肿瘤活性。在获得的化合物中，6i 具有最强的抗肿瘤活性，在 HL-60 细胞中的 IC50 值为 8.35 µM，在体内显示出与 H22 肝肿瘤中的环磷酰胺和 B16 黑色素瘤中的 5-氟尿嘧啶相似的抗肿瘤活性。

  DOI：

  10.3390/molecules17088832

文献信息

• Terpenoids. III: Synthesis and biological evaluation of 23-hydroxybetulinic acid derivatives as novel inhibitors of glycogen phosphorylase
  作者：Peiqing Zhu、Yi Bi、Jinyi Xu、Zan Li、Jun Liu、Luyong Zhang、Wencai Ye、Xiaoming Wu

  DOI：10.1016/j.bmcl.2009.10.055

  日期：2009.12

  A series of 23-hydroxybetulinic acid derivatives were prepared and tested in vitro as a new class of inhibitors of glycogen phosphorylase (GP). Within this series of compounds, 12b (IC50 = 3.5 μM) is the most potent GPa inhibitor. The preliminary SAR results of the 23-hydroxybetulinic acid derivatives are discussed.

  制备了一系列23-羟基甜菜酸衍生物，并作为一类新的糖原磷酸化酶（GP）抑制剂进行了体外测试。在这一系列化合物中，12b（IC 50  = 3.5μM）是最有效的GPa抑制剂。讨论了23-羟基贝丁酸衍生物的SAR初步结果。
• Synthesis and Biological Activity of 28-Amide Derivatives of 23-Hydroxy Betulinic Acid as Antitumor Agent Candidates
  作者：Yi Bi、Jinyi Xu、Fei Sun、Xiaoming Wu、Wencai Ye、Yijun Sun、Wenwen Huang

  DOI：10.2174/1573406411309070005

  日期：2013.8.1

  Based on the structure of 23-hydroxybetulinic acid (1), a series of 28-amide derivatives were synthesized. Biological evaluation in vitro for their antitumor activities against five cell lines (A549, BEL-7402, SF-763, B16 and HL-60) has indicated that compound 6g possesses the most effective antitumor activity with an IC50 value of 10.47 μM when treated with HL-60 cells. In vivo testing has also shown a comparable activity of 6g to cyclophosphamide against H22 liver tumor in mice and 5-fluorouracil against B16 melanoma, respectively.

  基于23-羟基倍半酸（1）的结构，合成了一系列28-酰胺衍生物。体外生物评估表明，这些衍生物在对抗五种细胞系（A549、BEL-7402、SF-763、B16和HL-60）的抗肿瘤活性中，化合物6g在处理HL-60细胞时展现出最有效的抗肿瘤活性，其IC50值为10.47 μM。体内测试也显示，6g对小鼠H22肝肿瘤的活性与环磷酰胺相当，对B16黑色素瘤的活性与5-氟尿嘧啶相当。
• Synthesis and cytotoxic activity of 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives
  作者：Yi Bi、Jinyi Xu、Xiaoming Wu、Wencai Ye、Shengtao Yuan、Luyong Zhang

  DOI：10.1016/j.bmcl.2006.09.096

  日期：2007.3

  New 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives were prepared and tested for cytotoxic activity on five cancer cell lines in vitro: all tested compounds showed stronger cytotoxic activity than 23-hydroxy betulinic acid and betulinic acid. In addition, compound 5a was tested for anti-tumor activity in vivo: it had much better anti-tumor activity than 23-OH betulinic acid and had similar anti-tumor activity with cyclophosphamide and 5-fluorouracil. (c) 2006 Elsevier Ltd. All rights reserved.