1-(thiomorpholin-4'-yl)-2,4-dinitrobenzene | 325733-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(thiomorpholin-4'-yl)-2,4-dinitrobenzene
• 英文别名: 4-(2,4-Dinitrophenyl)thiomorpholine
• CAS: 325733-46-8
• 化学式: C₁₀H₁₁N₃O₄S
• 分子量: 269.281
• InChiKey: JVZQGFFKDXLXGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(thiomorpholin-4'-yl)-2,4-dinitrobenzene 在 盐酸 作用下， 反应 36.0h， 以27%的产率得到2,4-dihydro-7-nitro-1H-[1,4]thiazino[4,3-a]benzimidazole 5-oxide
  参考文献：
  名称：

  2H-Benzimidazole 1,3-Dioxide Derivatives:  A New Family of Water-Soluble Anti-Trypanosomatid Agents

  摘要：

  Three series of benzimidazole N-oxide derivatives were developed and were examined for their activity against trypanosomatid parasites (Trypanosoma cruzi and Leishmania spp.). 2H-Benzimidazole 1,3-dioxides displayed remarkable in vitro activities against both parasites, with derivatives 28, 29, and 32 being the most potent (IC50 < 5 mu M) against the epimastigote form of T. cruzi and 28, 33, and 35 the most potent against the promastigote form of Leishmania spp. Unspecific cytotoxicity was evaluated using murine macrophages, and derivative 33 was not toxic at a concentration 30 times that of its IC50 against T. cruzi that was completely toxic for Leishmania spp., implying that the series of 2H-benzimidazole 1,3-dioxides is selective toward both trypanosomatid parasites. Derivatives 33 and 35 were submitted to an in vivo assay using an acute model of Chagas' disease and a short-term treatment (30 mg/kg/day orally administrated as aqueous solution, during 10 days). While in the control (untreated) and Benznidazole (50 mg/kg/day) groups survival fraction was 60.0% and 87.5%, respectively, none of the animals treated with derivatives 33 and 35 died. From the preliminary structure-activity relationship studies reduction potential and electrophilicity were found relevant to anti-T. cruzi activity. Active compounds are better electrophiles and more easily reduced than inactive ones.

  DOI：

  10.1021/jm0600343
• 作为产物：
  描述：

  硫代吗啉 、 1-氯-2,4-二硝基苯 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以79%的产率得到1-(thiomorpholin-4'-yl)-2,4-dinitrobenzene
  参考文献：
  名称：

  2H-Benzimidazole 1,3-Dioxide Derivatives:  A New Family of Water-Soluble Anti-Trypanosomatid Agents

  摘要：

  Three series of benzimidazole N-oxide derivatives were developed and were examined for their activity against trypanosomatid parasites (Trypanosoma cruzi and Leishmania spp.). 2H-Benzimidazole 1,3-dioxides displayed remarkable in vitro activities against both parasites, with derivatives 28, 29, and 32 being the most potent (IC50 < 5 mu M) against the epimastigote form of T. cruzi and 28, 33, and 35 the most potent against the promastigote form of Leishmania spp. Unspecific cytotoxicity was evaluated using murine macrophages, and derivative 33 was not toxic at a concentration 30 times that of its IC50 against T. cruzi that was completely toxic for Leishmania spp., implying that the series of 2H-benzimidazole 1,3-dioxides is selective toward both trypanosomatid parasites. Derivatives 33 and 35 were submitted to an in vivo assay using an acute model of Chagas' disease and a short-term treatment (30 mg/kg/day orally administrated as aqueous solution, during 10 days). While in the control (untreated) and Benznidazole (50 mg/kg/day) groups survival fraction was 60.0% and 87.5%, respectively, none of the animals treated with derivatives 33 and 35 died. From the preliminary structure-activity relationship studies reduction potential and electrophilicity were found relevant to anti-T. cruzi activity. Active compounds are better electrophiles and more easily reduced than inactive ones.

  DOI：

  10.1021/jm0600343

文献信息

• Structural studies of some 1-polymethyleneimino-2,4-dinitrobenzenesand related compounds; crystal structure of 1-(cis-2′,6′-dimethylpiperidin-1′-yl)-2,4-dinitrobenzene
  作者：Maureen F. Mackay、Douglas J. Gale、John F. K. Wilshire

  DOI：10.1071/ch00076

  日期：——

  The ultraviolet and 1H n.m.r. spectra of some1-polymethyleneimino-2,4-dinitrobenzenes and related compounds are discussed.The effect of trifluoroacetic acid on these spectra was also investigated;with 1-azetidinyl-2,4-dinitrobenzene, acid-catalysed ring opening wasobserved. The solid-state conformation of1-(cis-2′,6′-dimethylpiperidin-1′-yl)-2,4-dinitrobenzenehas been defined by single-crystal X-ray

  讨论了一些1-聚亚甲基亚氨基-2,4-二硝基苯和相关化合物的紫外和1H nmr光谱。还研究了三氟乙酸对这些光谱的影响；1-氮杂环丁烷基-2,4-二硝基苯，酸催化开环被观测到。1-(cis-2',6'-二甲基哌啶-1'-基)-2,4-二硝基苯的固态构象已通过单晶X射线晶体学确定。三斜晶体属于空间群 P-1，a 8.165(1)、b 7.865(1)、c 11.148(1) Å、α 95.23(1)、β 106.00(1)、γ 92.63(1)˚ 和 Z 2。对于 2222 个观测数据，该结构被细化为 0.048 的最终 R。在晶体中，苯环呈轻微的船形构象，而氨基和邻硝基从环的平均平面明显扭曲。