(1R,4R/S,5R,8R)-4,8-dimethyl-8-ethoxyoxalyloxy-4-phenyl-sulfenylmethyl-2,3-dioxabicyclo[3.3.1]nonane | 221293-38-5

• 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: (1R,4R/S,5R,8R)-4,8-dimethyl-8-ethoxyoxalyloxy-4-phenyl-sulfenylmethyl-2,3-dioxabicyclo[3.3.1]nonane
• CAS: 221293-38-5
• 化学式: C₂₀H₂₆O₆S
• 分子量: 394.489
• InChiKey: MENSLZOHLZRJMM-BLWCJUTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,4R/S,5R,8R)-4,8-dimethyl-8-ethoxyoxalyloxy-4-phenyl-sulfenylmethyl-2,3-dioxabicyclo[3.3.1]nonane 在 间氯过氧苯甲酸 作用下， 生成 (1R,4S,5R,8R)-4,8-dimethyl-8-ethoxyoxalyloxy-4-phenylsulfonylmethyl-2,3-dioxabicyclo[3.3.1]nonane 、 (1R,4R,5R,8R)-4,8-dimethyl-8-ethoxyoxalyloxy-4-phenylsulfonylmethyl-2,3-dioxabicyclo[3.3.1]nonane
  参考文献：
  名称：

  砜内过氧化物的合成及其体外抗疟活性。

  摘要：

  通过短而有效的方法，由R制备了一系列在8位（4）带有多个取代基的4,8-二甲基-4-苯基磺酰基甲基-2,3-二氧杂双环[3.3.1] + ++壬烷-（+）-柠檬烯。关键反应包括硫醇氧共氧化，以及与内过氧官能团相容的位阻叔醇的烷基化和酰化。已发现在结构上与yingzhaosu A（2）有关的某些化合物4具有与青蒿素（1）相当的体外抗疟活性，并优于arteflene（3）。

  DOI：

  10.1016/s0960-894x(98)00141-3
• 作为产物：
  描述：

  (1R,4R/S,5R,8R)-4,8-dimethyl-4-phenylsulfenylmethyl-8-trimethylsilyloxy-2,3-dioxabicyclo[3.3.1]nonane 在 2,6-二甲基吡啶 作用下， 生成 (1R,4R/S,5R,8R)-4,8-dimethyl-8-ethoxyoxalyloxy-4-phenyl-sulfenylmethyl-2,3-dioxabicyclo[3.3.1]nonane
  参考文献：
  名称：

  砜内过氧化物的合成及其体外抗疟活性。

  摘要：

  通过短而有效的方法，由R制备了一系列在8位（4）带有多个取代基的4,8-二甲基-4-苯基磺酰基甲基-2,3-二氧杂双环[3.3.1] + ++壬烷-（+）-柠檬烯。关键反应包括硫醇氧共氧化，以及与内过氧官能团相容的位阻叔醇的烷基化和酰化。已发现在结构上与yingzhaosu A（2）有关的某些化合物4具有与青蒿素（1）相当的体外抗疟活性，并优于arteflene（3）。

  DOI：

  10.1016/s0960-894x(98)00141-3

文献信息

• A Short Synthesis and Biological Evaluation of Potent and Nontoxic Antimalarial Bridged Bicyclic β-Sulfonyl-Endoperoxides
  作者：Mario D. Bachi、Edward E. Korshin、Roland Hoos、Alex M. Szpilman、Poonsakdi Ploypradith、Suji Xie、Theresa A. Shapiro、Gary H. Posner

  DOI：10.1021/jm020584a

  日期：2003.6.1

  The syntheses and in vitro antimalarial. screening of 50 bridged, bicyclic endoperoxides of types 9-13 are reported. In contrast to antimalarial trioxanes of the artemisinin family, but like yingzhaosu A and arteflene, the peroxide function of compounds 9-13 is contained in a 2,3dioxabicyclo[3.3.1]nonane system 6. Peroxides 9 and 10 (RI = OH) are readily available through a multicomponent, sequential, free-radical reaction involving thiol-monoterpenes co-oxygenation (a TOCO reaction). beta-Sulfenyl peroxides 9 and 10 (R-1 = OH) are converted into beta-sulfinyl and beta-sulfonyl peroxides of types 11-13 by controlled S-oxidation and manipulation of the tert-hydroxyl. group through acylation, alkylation, or dehydration followed by selective hydrogenation. Ten enantiopure beta-sulfbnyl peroxides of types 12 and 13 exhibit in vitro antimalarial activity comparable to that of artemisinin (IC50 = 6-24 nM against Plasmodium falciparum NF54). In vivo testing of a few selected peroxides against Plasmodium berghei N indicates that the antimalarial efficacies of beta-sulfonyl peroxides 39a, 46a, 46b, and 50a are comparable to those of some of the best antimalarial drugs and are higher than artemisinin against chloroquine-resistant Plasmodium yoelii ssp. NS. In view of the nontoxicity of beta-sulfonyl peroxides 39a, 46a, and 46b in mice, at high dosing, these compounds are regarded as promising antimalarial drug candidates.