4,6-bis-azidomethyl-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione | 172327-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡唑类
• 英文名称: 4,6-bis-azidomethyl-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione
• 英文别名: 1,7-Bis(azidomethyl)-2,6-dimethylpyrazolo[1,2-a]pyrazole-3,5-dione
• CAS: 172327-16-1
• 化学式: C₁₀H₁₀N₈O₂
• 分子量: 274.242
• InChiKey: CDCKDMWJPUOLMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6-bis-azidomethyl-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione 在 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 4,6-(1,17-(2,16-diaza-3,15-dioxo-9-oxothiaheptadecamethylene))-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione
  参考文献：
  名称：

  Bimane cyclic esters, possible stereologues of trypanothione as antitrypanosomal agents. Bimanes 29

  摘要：

  Tricyclic esters derived from bimanes have been synthesized with ring sizes near or equal to that of trypanothione disulfide (T(S)(2)), a bis-glutathionylspermidine that is involved in regulating the thiol status of Leishmania and other trypanosomatids. Modest activity for many of the compounds against Leishmania donovani with a maximum at the T(S)(2) ring size suggests that the esters act as T(S)(2) surrogates. However, no inhibition of T(S)(2)-reductase is observed for a number of the compounds. A series of tricyclic bimane amides with structures more closely analogous to T(S)2 are inactive in biological tests, New approaches were developed for the synthesis of the amides. The surprising effectiveness of the cyclic ester synthesis is explained. Acid chloride formation catalyzed by sulfides is briefly described.

  DOI：

  10.1016/0223-5234(96)88283-3
• 作为产物：
  描述：

  3,5-双溴甲基-2,6-二甲基吡唑并[1,2-a]吡唑-1,7-二酮 在 sodium azide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以68%的产率得到4,6-bis-azidomethyl-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione
  参考文献：
  名称：

  Bimane cyclic esters, possible stereologues of trypanothione as antitrypanosomal agents. Bimanes 29

  摘要：

  Tricyclic esters derived from bimanes have been synthesized with ring sizes near or equal to that of trypanothione disulfide (T(S)(2)), a bis-glutathionylspermidine that is involved in regulating the thiol status of Leishmania and other trypanosomatids. Modest activity for many of the compounds against Leishmania donovani with a maximum at the T(S)(2) ring size suggests that the esters act as T(S)(2) surrogates. However, no inhibition of T(S)(2)-reductase is observed for a number of the compounds. A series of tricyclic bimane amides with structures more closely analogous to T(S)2 are inactive in biological tests, New approaches were developed for the synthesis of the amides. The surprising effectiveness of the cyclic ester synthesis is explained. Acid chloride formation catalyzed by sulfides is briefly described.

  DOI：

  10.1016/0223-5234(96)88283-3