methyl (4R,4aR,6aR,7R,9R,11aS,11bR)-7-hydroxy-11b-methyl-8-methylene-2-(2-tosylhydrazineylidene)tetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate | 926026-17-7

• 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 (4R,4aR,6aR,7R,9R,11aS,11bR)-7-hydroxy-11b-methyl-8-methylene-2-(2-tosylhydrazineylidene)tetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate
• CAS: 926026-17-7
• 化学式: C₂₇H₃₆N₂O₅S
• 分子量: 500.659
• InChiKey: RRSOQDSHBRDCHG-LFHJYYBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  105.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (4R,4aR,6aR,7R,9R,11aS,11bR)-7-hydroxy-11b-methyl-8-methylene-2-(2-tosylhydrazineylidene)tetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate 在 sodium cyanoborohydride 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 环丁砜 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 methyl (1R,4R,5R,9R,10S,13R)-9-methyl-14-methylidene-15-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
  参考文献：
  名称：

  Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

  摘要：

  Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 mu M, respectively. These two 1-analogues are promising lead compounds for further investigation.

  DOI：

  10.1021/np060504w
• 作为产物：
  描述：

  2,15-diketoatractyligenin methyl ester 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 12.17h， 生成 methyl (4R,4aR,6aR,7R,9R,11aS,11bR)-7-hydroxy-11b-methyl-8-methylene-2-(2-tosylhydrazineylidene)tetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate
  参考文献：
  名称：

  Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

  摘要：

  Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 mu M, respectively. These two 1-analogues are promising lead compounds for further investigation.

  DOI：

  10.1021/np060504w