9,10-dioxa-syn-(bromomethyl,chloro)bimane | 102284-82-2

• 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: 9,10-dioxa-syn-(bromomethyl,chloro)bimane
• 英文别名: 4,6-dibromomethyl-3,7-dimethyl-1,5-diazabicyclo<3.3.0>octa-3,6-diene-2,8-dione；1,7-Bis(bromomethyl)-2,6-dichloropyrazolo[1,2-a]pyrazole-3,5-dione
• CAS: 102284-82-2
• 化学式: C₈H₄Br₂Cl₂N₂O₂
• 分子量: 390.846
• InChiKey: YTENHWJFMJTVLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-dioxa-syn-(bromomethyl,chloro)bimane 在 sodium sulfide 、 phosphate buffer 、 十六烷基三甲基溴化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 4.5h， 生成 1,4-Dichloro-6,6-dioxo-6,7-dihydro-5H-6λ⁶-thia-2a,7b-diaza-cyclopenta[cd]indene-2,3-dione
  参考文献：
  名称：

  Kosower, Edward M.; Pazhenchevsky, Barak; Marciano, Daniele, Journal of the American Chemical Society, 1990, vol. 112, # 20, p. 7315 - 7319

  摘要：

  DOI：
• 作为产物：
  描述：

  syn-(methyl,chloro)bimane 在 溴 作用下， 反应 2.0h， 以67%的产率得到9,10-dioxa-syn-(bromomethyl,chloro)bimane
  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

• Bimanes. 23. The synthesis and properties of vinyl-9,10-dioxabimanes
  作者：Edward M. Kosower、David Zbaida、Michel Baud'huin、Daniele Marciano、Israel Goldberg

  DOI：10.1021/ja00176a034

  日期：1990.9

  Syntheses and useful reactions of syn-vinylbimanes are reported. The precursors are syn-(ethyl,methyl)bimane (4,6-diethyl-3,7-dimethyl-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione) (syn-(CH 3 CH 2 ,CH 3 )B) (2) and syn-(ethyl,chloro)bimane (4,6-diethyl-3,7-dichloro-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione) (syn-(CH 3 CH 2 ,Cl)B) (4)

  合成和有用的合成-乙烯基二甲胺的反应已被报道。前体是syn-(ethyl,methyl)bimane (4,6-diethyl-3,7-dimethyl-1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione) (syn -(CH 3 CH 2 ,CH 3 )B) (2) 和syn-(ethyl,chloro)bimane (4,6-diethyl-3,7-dichloro-1,5-diazabicyclo[3.3.0]octa-3 ,6-diene-2,8-dione) (syn-(CH 3 CH 2 ,Cl)B) (4)
• Bimanes. 17. (Haloalkyl)-1,5-diazabicyclo[3.3.O]octadienediones (halo-9,10-dioxabimanes): reactivity toward the tripeptide thiol, glutathione
  作者：Annette E. Radkowsky、Edward M. Kosower

  DOI：10.1021/ja00275a045

  日期：1986.7
• KOSOWER, EDWARD M.;ZBAIDA, DAVID;BAUDHUIN, MICHEL;MARCIANO, DANIELE;GOLDB+, J. AMER. CHEM. SOC., 112,(1990) N0, C. 7305-7314
  作者：KOSOWER, EDWARD M.、ZBAIDA, DAVID、BAUDHUIN, MICHEL、MARCIANO, DANIELE、GOLDB+

  DOI：——

  日期：——
• 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.
• Kosower, Edward M.; Pazhenchevsky, Barak; Marciano, Daniele, Journal of the American Chemical Society, 1990, vol. 112, # 20, p. 7315 - 7319
  作者：Kosower, Edward M.、Pazhenchevsky, Barak、Marciano, Daniele、Baud'huin, Michel、Bendel, Peter、Hermolin, Joshua、Goldberg, Israel

  DOI：——

  日期：——