3-oxime 20,29-dihydrobetulonic acid

• 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: 3-oxime 20,29-dihydrobetulonic acid
• 英文别名: 3-hydroxyloxime-20,29-dihydrobetulonic acid；(1S,3aS,5aR,5bR,7aR,9E,11aR,11bR,13aR,13bR)-9-hydroxyimino-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• 化学式: C₃₀H₄₉NO₃
• 分子量: 471.724
• InChiKey: YAERKPJXSZHFQI-NQXGGYSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-oxime 20,29-dihydrobetulonic acid 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 生成 3-amino-20,29-dihydrobetulinic acid
  参考文献：
  名称：

  Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents

  摘要：

  New 3-O-acyl, 3-benzylidene, 3-hydrazone, 3-hydrazine, 17-carboxyacryloyl ester derivatives of betulinic acid (2-6, 8-11, 13, 17, 18, 21, and 22) were synthesized and evaluated in vitro for anti-angiogenic activity on endothelial cell cytotoxicity, specificity, and tube-formation ability. All derivatives reported here showed IC50 < 4 mug/mL. Compounds 3, 9, 10, 17, 21, and 22 have shown better cytotoxicity (IC50 < 1.2 mug/mL) than betulinic acid (1) and improved endothelial cell specificity (ECS > 10) in some cases. Compounds 10, 17, and 18 have shown 20%, 32%, and 48% reduction in TLS, respectively, and were found better than betulinic acid (1). We have shown that 20,29-dihydrobetulinic acid derivatives have better anti-angiogenic activity as compared to betulinic acid or its other derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.010
• 作为产物：
  描述：

  白桦脂酸 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 硫酸 、 盐酸羟胺 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-oxime 20,29-dihydrobetulonic acid
  参考文献：
  名称：

  Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents

  摘要：

  New 3-O-acyl, 3-benzylidene, 3-hydrazone, 3-hydrazine, 17-carboxyacryloyl ester derivatives of betulinic acid (2-6, 8-11, 13, 17, 18, 21, and 22) were synthesized and evaluated in vitro for anti-angiogenic activity on endothelial cell cytotoxicity, specificity, and tube-formation ability. All derivatives reported here showed IC50 < 4 mug/mL. Compounds 3, 9, 10, 17, 21, and 22 have shown better cytotoxicity (IC50 < 1.2 mug/mL) than betulinic acid (1) and improved endothelial cell specificity (ECS > 10) in some cases. Compounds 10, 17, and 18 have shown 20%, 32%, and 48% reduction in TLS, respectively, and were found better than betulinic acid (1). We have shown that 20,29-dihydrobetulinic acid derivatives have better anti-angiogenic activity as compared to betulinic acid or its other derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.010

文献信息

• Synthesis and cytotoxic activity of 3-O-acyl/3-hydrazine /2-bromo/20,29-dibromo betulinic acid derivatives
  作者：Rama Mukherjee、Manu Jaggi、Mohammad J.A Siddiqui、Sanjay K Srivastava、Praveen Rajendran、Anand Vardhan、Anand C Burman

  DOI：10.1016/j.bmcl.2004.05.034

  日期：2004.8

  A series of 3-O-acyl, 3-hydrazine, 2-bromo, and 20,29-dibromo betulinic acid derivatives (1-27) have been synthesized and screened for in vitro cytotoxic activity on human cancer cell lines MOLT-4, JurkatE6.1, CEM.CM3, BRISTOL8, U937, DU145, PA-1 A549, and L132. A number of compounds have shown ED50 < 1 mug/mL against the cancer cell lines tested and have shown better cytotoxicity than betulinic acid. Compounds 13, 19, 20, 23, and 27 were the best derivatives and were selected as lead molecules for further development. The structure-activity relationship has been described. (C) 2004 Elsevier Ltd. All rights reserved.