4,6-(1,13-(2,12-dioxa-3,11-dioxo-7-thia-tridecamethylene))-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 4,6-(1,13-(2,12-dioxa-3,11-dioxo-7-thia-tridecamethylene))-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione
• 英文别名: 16,20-Dimethyl-3,13-dioxa-8-thia-18,21-diazatricyclo[13.5.1.018,21]henicosa-1(20),15-diene-4,12,17,19-tetrone
• 化学式: C₁₈H₂₂N₂O₆S
• 分子量: 394.448
• InChiKey: AVCNFVHMFCGQRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 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 、 以 乙腈 为溶剂， 以40%的产率得到4,6-(1,13-(2,12-dioxa-3,11-dioxo-7-thia-tridecamethylene))-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

文献信息

• Bimane cyclic esters, possible stereologues of trypanothione as antitrypanosomal agents. Bimanes 29
  作者：EM Kosower、AE Radkowsky、AH Fairlamb、SL Croft、RA Neal

  DOI：10.1016/0223-5234(96)88283-3

  日期：1995.1

  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.