3-aza-A-homocholest-3,6-dione | 1338566-50-9

• 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: 3-aza-A-homocholest-3,6-dione
• 英文别名: (1S,2R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-5-azatetracyclo[9.7.0.02,8.012,16]octadecane-6,9-dione
• CAS: 1338566-50-9
• 化学式: C₂₇H₄₅NO₂
• 分子量: 415.66
• InChiKey: HLGWMHLVHREFEL-SRTNJPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-aza-A-homocholest-3,6-dione 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 1.17h， 以81%的产率得到6-hydroximino-3-aza-A-homocholest-3-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactams

  摘要：

  Using cholesterol as starting material, a series of 6-substituted-3-aza-A-homo-3-oxycholestanes and 6-substituted-4-aza-A-homo-3-oxycholestanes were synthesized by the oxidation, reduction, oximation, Beckman rearrangement and condensation reaction. These synthesized compounds displayed a distinct cytotoxicity against MGC 7901, HeLa and SMMC 7404 cancer cells. Our results revealed that the structures of functional groups at position-6 on the steroidal ring are crucial for the IC50 value of antiproliferative activities of these compounds and the cytotoxic activity against MGC 7901 and SMMC 7404 cells was not significantly different between 4-N-lactams and 3-N-lactams when its 6-substituted group was a carbonyl or a hydroximino, but all 3-N-lactams showed a higher cytotoxicity against HeLa cells than 4-N-lactams. In particular, compounds 6, 8, 9 (IC50 6: 6.5 mu mol/L; 8: 7.7 mu mol/L; 9: 5.6 mu mol/L) were even more cytotoxic than cisplatin to HeLa cells (positive contrast, 10.1 mu mol/L). The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.06.013
• 作为产物：
  描述：

  (3E)-hydroxyiminocholest-6-one 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以45%的产率得到4-aza-A-homocholest-3,6-dione
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some steroidal lactams

  摘要：

  Using cholesterol as starting material, a series of 6-substituted-3-aza-A-homo-3-oxycholestanes and 6-substituted-4-aza-A-homo-3-oxycholestanes were synthesized by the oxidation, reduction, oximation, Beckman rearrangement and condensation reaction. These synthesized compounds displayed a distinct cytotoxicity against MGC 7901, HeLa and SMMC 7404 cancer cells. Our results revealed that the structures of functional groups at position-6 on the steroidal ring are crucial for the IC50 value of antiproliferative activities of these compounds and the cytotoxic activity against MGC 7901 and SMMC 7404 cells was not significantly different between 4-N-lactams and 3-N-lactams when its 6-substituted group was a carbonyl or a hydroximino, but all 3-N-lactams showed a higher cytotoxicity against HeLa cells than 4-N-lactams. In particular, compounds 6, 8, 9 (IC50 6: 6.5 mu mol/L; 8: 7.7 mu mol/L; 9: 5.6 mu mol/L) were even more cytotoxic than cisplatin to HeLa cells (positive contrast, 10.1 mu mol/L). The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.06.013

文献信息

• Synthesis and antiproliferative activity of some steroidal lactams
  作者：Yanmin Huang、Jianguo Cui、Sijing Chen、Chunfang Gan、Aimin Zhou

  DOI：10.1016/j.steroids.2011.06.013

  日期：2011.11

  Using cholesterol as starting material, a series of 6-substituted-3-aza-A-homo-3-oxycholestanes and 6-substituted-4-aza-A-homo-3-oxycholestanes were synthesized by the oxidation, reduction, oximation, Beckman rearrangement and condensation reaction. These synthesized compounds displayed a distinct cytotoxicity against MGC 7901, HeLa and SMMC 7404 cancer cells. Our results revealed that the structures of functional groups at position-6 on the steroidal ring are crucial for the IC50 value of antiproliferative activities of these compounds and the cytotoxic activity against MGC 7901 and SMMC 7404 cells was not significantly different between 4-N-lactams and 3-N-lactams when its 6-substituted group was a carbonyl or a hydroximino, but all 3-N-lactams showed a higher cytotoxicity against HeLa cells than 4-N-lactams. In particular, compounds 6, 8, 9 (IC50 6: 6.5 mu mol/L; 8: 7.7 mu mol/L; 9: 5.6 mu mol/L) were even more cytotoxic than cisplatin to HeLa cells (positive contrast, 10.1 mu mol/L). The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.