(1R,2R,14R,17R,18R,21S,24S,25R,26R)-7-chloro-2,13,13,17,18-pentamethyl-24-propan-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5(10),6,8-tetraene-21-carboxylic acid | 905837-98-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1R,2R,14R,17R,18R,21S,24S,25R,26R)-7-chloro-2,13,13,17,18-pentamethyl-24-propan-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5(10),6,8-tetraene-21-carboxylic acid
• CAS: 905837-98-1
• 化学式: C₃₆H₅₀ClNO₂
• 分子量: 564.251
• InChiKey: UIRSEPOFNKXUGW-HIFHRDMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-oxolupan-28-ic acid 、 4-氯苯肼 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (1R,2R,14R,17R,18R,21S,24S,25R,26R)-7-chloro-2,13,13,17,18-pentamethyl-24-propan-2-yl-11-azaheptacyclo[15.11.0.02,14.04,12.05,10.018,26.021,25]octacosa-4(12),5(10),6,8-tetraene-21-carboxylic acid
  参考文献：
  名称：

  Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives

  摘要：

  A new series of betulinic acid derivatives have been synthesized by introducing heterocyclic ring between C-2 and C-3 positions of betulinic acid. Further modi. cations were also carried out by reduction of C-20(29) unsaturated bond and substitution of C-28 carboxyl group by ester and amide linkage to enhance the selectivity. Compound 11 resulted in IC50 of 2.44, 2.5, and 2.7 mu g/ml on MIAPaCa, PA-1, and SW620 cancer cell lines, respectively. Compound 38 resulted in IC50 of 0.67 mu g/ml on MIAPaCa cell line. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.003

文献信息

• Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives
  作者：Vivek Kumar、Nidhi Rani、Pawan Aggarwal、Vinod K. Sanna、Anu T. Singh、Manu Jaggi、Narendra Joshi、Pramod K. Sharma、Raghuveer Irchhaiya、Anand C. Burman

  DOI：10.1016/j.bmcl.2008.08.003

  日期：2008.9

  A new series of betulinic acid derivatives have been synthesized by introducing heterocyclic ring between C-2 and C-3 positions of betulinic acid. Further modi. cations were also carried out by reduction of C-20(29) unsaturated bond and substitution of C-28 carboxyl group by ester and amide linkage to enhance the selectivity. Compound 11 resulted in IC50 of 2.44, 2.5, and 2.7 mu g/ml on MIAPaCa, PA-1, and SW620 cancer cell lines, respectively. Compound 38 resulted in IC50 of 0.67 mu g/ml on MIAPaCa cell line. (C) 2008 Elsevier Ltd. All rights reserved.