1,2-dimethyl-4-phenylsulfonylmethyl-5-nitroimidazole | 116248-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2-dimethyl-4-phenylsulfonylmethyl-5-nitroimidazole
• 英文别名: 4-[(Benzenesulfonyl)methyl]-1,2-dimethyl-5-nitro-1H-imidazole；4-(benzenesulfonylmethyl)-1,2-dimethyl-5-nitroimidazole
• CAS: 116248-42-1
• 化学式: C₁₂H₁₃N₃O₄S
• 分子量: 295.319
• InChiKey: BRIXTKQXSTVPBV-UHFFFAOYSA-N

物化性质

• 熔点：
  195-197 °C
• 沸点：
  574.5±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲硝咪唑 、 氯甲基苯砜 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以28%的产率得到1,2-dimethyl-4-phenylsulfonylmethyl-5-nitroimidazole
  参考文献：
  名称：

  Lowering of 5-nitroimidazole's mutagenicity: Towards optimal antiparasitic pharmacophore

  摘要：

  To improve the antiparasitic pharmacophore, 20 5-nitroimidazoles bearing an arylsulfonylmethyl group were prepared from commercial imidazoles. The antiparasitic activity of these molecules was assessed against Trichomonas vaginalis, the in vitro cytotoxicity was evaluated on human monocytes and the mutagenicity was determined by the Salmonella mutagenicity assay. All IC50 on T. vaginalis were below the one of metronidazole. The determination of the specificity indexes (SIs), defined as the ratios of the cytotoxic activity and the antitrichomonas activity, indicated that 11 derivatives had a SI over the one of metronidazole. Molecules, bearing an additional methyl group on the 2-position, showed a lower mutagenicity than metronidazole. Moreover, three derivatives were characterized by a low mutagenicity and an efficient antitrichomonas activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.015

文献信息

• Makosza, Mieczyslaw; Kwast, Ewa, Bulletin of the Polish Academy of Sciences: Chemistry, 1987, vol. 35, # 7-8, p. 287 - 292
  作者：Makosza, Mieczyslaw、Kwast, Ewa

  DOI：——

  日期：——
• Rapid Synthesis of New 5‐Nitroimidazoles as Potential Antibacterial Drugs <i>via</i> VNS Procedure
  作者：Maxime D. Crozet、Vincent Rémusat、Christophe Curti、Patrice Vanelle

  DOI：10.1080/00397910600943873

  日期：2006.11.1

  Original 4-arylsulfonylmethyl-5-nitroimidazoles were prepared by reacting four chloromethylaryl sulfones with 5-nitroimidazole derivatives via a vicarious nucleophilic substitution (VNS) of hydrogen reaction.
• MAKOSZA, MIECZYSLAW;KWAST, EWA, BULL. POL. ACAD. SCI. CHEM., 35,(1987) N 7-8, 287-292
  作者：MAKOSZA, MIECZYSLAW、KWAST, EWA

  DOI：——

  日期：——
• Lowering of 5-nitroimidazole's mutagenicity: Towards optimal antiparasitic pharmacophore
  作者：Maxime D. Crozet、Céline Botta、Monique Gasquet、Christophe Curti、Vincent Rémusat、Sébastien Hutter、Olivier Chapelle、Nadine Azas、Michel De Méo、Patrice Vanelle

  DOI：10.1016/j.ejmech.2008.05.015

  日期：2009.2

  To improve the antiparasitic pharmacophore, 20 5-nitroimidazoles bearing an arylsulfonylmethyl group were prepared from commercial imidazoles. The antiparasitic activity of these molecules was assessed against Trichomonas vaginalis, the in vitro cytotoxicity was evaluated on human monocytes and the mutagenicity was determined by the Salmonella mutagenicity assay. All IC50 on T. vaginalis were below the one of metronidazole. The determination of the specificity indexes (SIs), defined as the ratios of the cytotoxic activity and the antitrichomonas activity, indicated that 11 derivatives had a SI over the one of metronidazole. Molecules, bearing an additional methyl group on the 2-position, showed a lower mutagenicity than metronidazole. Moreover, three derivatives were characterized by a low mutagenicity and an efficient antitrichomonas activity. (C) 2008 Elsevier Masson SAS. All rights reserved.