α-hydroperoxydeoxyartemisitene | 405304-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: α-hydroperoxydeoxyartemisitene
• 英文别名: (1S,4S,5R,8S,10S,12R,13R)-10-hydroperoxy-1,5-dimethyl-9-methylidene-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecane
• CAS: 405304-84-9
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: ICQWJCPEHPZJOX-UQCWRGLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-hydroperoxydeoxyartemisitene 在 polymer-bound triphenylphosphine 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以92%的产率得到dihydrodeoxyartemisitene
  参考文献：
  名称：

  Deoxyartemisinin Derivatives from Photooxygenation of Anhydrodeoxydihydroartemisinin and Their Cytotoxic Evaluation

  摘要：

  Photooxygenation of anhydrodeoxydihydroartemisinin (4) followed by chromatographic separation of the reaction mixture yielded the new compounds alpha- (5) and beta-hydroperoxydeoxyartemisitene (8) and the formate ester 7, together with two previously reported compounds, 6 and 9. Reduction of 5 using polymer-bound triphenylphosphine afforded the new compound dihydrodeoxyartemisitene (10). Treatment of 10 with a catalytic amount of BF3-OEt2 yielded the C-2-symmetrical dimer bis(dihydrodeoxyartemisitene) ether (11) and two new compounds, dihydrodeoxyartemisitene methyl ether (12) and the dimer 13, as minor products. Dehydroacetoxylation of 5 using acetic anhydride in pyridine afforded deoxyartemisitene (14). The identities of the new compounds (5, 7, 8, 10-14) were deduced from their spectral data and by chemical derivatization. The stereochemistry of dimer 11 was defined on the basis of X-ray crystallographic analysis. All compounds were evaluated in vitro in the National Cancer Institute drug-screening program consisting of 60 human cancer, cell lines derived from nine different tissues. Of the compounds tested, deoxyartemisitene (14) demonstrated significant cytotoxicity against a number of human cancer cell lines.

  DOI：

  10.1021/np0104065
• 作为产物：
  描述：

  anhydrodeoxydihydroartemisinin 在 5,10,15,20-tetrakisphenylporphyrin 、 氧气 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 以55%的产率得到α-hydroperoxydeoxyartemisitene
  参考文献：
  名称：

  Deoxyartemisinin Derivatives from Photooxygenation of Anhydrodeoxydihydroartemisinin and Their Cytotoxic Evaluation

  摘要：

  Photooxygenation of anhydrodeoxydihydroartemisinin (4) followed by chromatographic separation of the reaction mixture yielded the new compounds alpha- (5) and beta-hydroperoxydeoxyartemisitene (8) and the formate ester 7, together with two previously reported compounds, 6 and 9. Reduction of 5 using polymer-bound triphenylphosphine afforded the new compound dihydrodeoxyartemisitene (10). Treatment of 10 with a catalytic amount of BF3-OEt2 yielded the C-2-symmetrical dimer bis(dihydrodeoxyartemisitene) ether (11) and two new compounds, dihydrodeoxyartemisitene methyl ether (12) and the dimer 13, as minor products. Dehydroacetoxylation of 5 using acetic anhydride in pyridine afforded deoxyartemisitene (14). The identities of the new compounds (5, 7, 8, 10-14) were deduced from their spectral data and by chemical derivatization. The stereochemistry of dimer 11 was defined on the basis of X-ray crystallographic analysis. All compounds were evaluated in vitro in the National Cancer Institute drug-screening program consisting of 60 human cancer, cell lines derived from nine different tissues. Of the compounds tested, deoxyartemisitene (14) demonstrated significant cytotoxicity against a number of human cancer cell lines.

  DOI：

  10.1021/np0104065

文献信息

• Deoxyartemisinin Derivatives from Photooxygenation of Anhydrodeoxydihydroartemisinin and Their Cytotoxic Evaluation
  作者：Ahmed M. Galal、Samir A. Ross、Mahmoud A. ElSohly、Hala N. ElSohly、Farouk S. El-Feraly、Mohamed S. Ahmed、Andrew T. McPhail

  DOI：10.1021/np0104065

  日期：2002.2.1

  Photooxygenation of anhydrodeoxydihydroartemisinin (4) followed by chromatographic separation of the reaction mixture yielded the new compounds alpha- (5) and beta-hydroperoxydeoxyartemisitene (8) and the formate ester 7, together with two previously reported compounds, 6 and 9. Reduction of 5 using polymer-bound triphenylphosphine afforded the new compound dihydrodeoxyartemisitene (10). Treatment of 10 with a catalytic amount of BF3-OEt2 yielded the C-2-symmetrical dimer bis(dihydrodeoxyartemisitene) ether (11) and two new compounds, dihydrodeoxyartemisitene methyl ether (12) and the dimer 13, as minor products. Dehydroacetoxylation of 5 using acetic anhydride in pyridine afforded deoxyartemisitene (14). The identities of the new compounds (5, 7, 8, 10-14) were deduced from their spectral data and by chemical derivatization. The stereochemistry of dimer 11 was defined on the basis of X-ray crystallographic analysis. All compounds were evaluated in vitro in the National Cancer Institute drug-screening program consisting of 60 human cancer, cell lines derived from nine different tissues. Of the compounds tested, deoxyartemisitene (14) demonstrated significant cytotoxicity against a number of human cancer cell lines.