奥硝唑杂质5 | 16773-51-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 奥硝唑杂质5
• 英文名称: 1-(2,3-epoxypropyl)-2-methyl-4-nitroimidazole
• 英文别名: 2-methyl-4-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole；1-(2,3-Epoxypropyl)-2-methyl-4-nitroimidazol；1-(1,2-Epoxy-propyl)-2-methyl-4-nitro-imidazol；2-methyl-4-nitro-1-oxiranylmethyl-1H-imidazole；1H-Imidazole, 2-methyl-4-nitro-1-(oxiranylmethyl)-；2-methyl-4-nitro-1-(oxiran-2-ylmethyl)imidazole
• CAS: 16773-51-6
• 化学式: C₇H₉N₃O₃
• 分子量: 183.167
• InChiKey: TUHYOMJIXVHZLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  4

制备方法与用途

该产品是奥硝唑的杂质之一，具备一定的抗菌特性。

反应信息

• 作为反应物：
  描述：

  奥硝唑杂质5 在 pyridinium polyhydrogenfluoride 作用下， 反应 3.0h， 以47%的产率得到1-(3-氟-2-羟基丙基)-2-甲基-4-硝基咪唑
  参考文献：
  名称：

  Lipase-catalyzed resolution of both enantiomers of Ornidazole and some analogues

  摘要：

  The resolution of the enantiomers of the chemotherapeutic Ornidazole (Tiberal((R))) 1a was achieved by acetylation of the racemic compound with vinylacetate in the presence of lipase Amano PS (from Pseudomonas cepacia). The halogen analogues 4a-6a and the corresponding 4-nitro-derivatives 1b and 4b-6b were also synthesized and the enantiomers were separated by kinetic enzymatic resolution. The absolute configuration of two compounds was determined by X-ray crystallography. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00260-7
• 作为产物：
  描述：

  奥硝唑异构体 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.75h， 以86%的产率得到奥硝唑杂质5
  参考文献：
  名称：

  2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas : Design, synthesis, biology and 3D-QSAR study

  摘要：

  Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T. vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole derivatives was synthesized via nucleophilic ring opening reaction of epoxide and the efficacies against drug-susceptible and -resistant Trichomonas vaginalis were evaluated. All the molecules except two were found to be active against both susceptible and resistant strains with MICs ranging 8.55-336.70 mu M and 28.80-1445.08 mu M, respectively. Most of the compounds were remarkably more effective than the standard Metronidazole. This study analyzes the in vitro and in vivo activities of the new 5-nitroimidazoles, which were found to be safe against human cervical HeLa cells with good selectivity index. The exploration of SAR by the synthesis of four different prototypes and 3D-QSAR study has shown the importance of prototype 1 over other prototypes. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.006

文献信息

• Ahmed; Stratford; Jenkins, Arzneimittel-Forschung/Drug Research, 1985, vol. 35, # 12, p. 1763 - 1768
  作者：Ahmed、Stratford、Jenkins

  DOI：——

  日期：——
• Improvements relating to compounds useful in radiotherapy or chemotherapy
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0095906B1

  公开（公告）日：1986-10-22
• SUWINSKI J.; SALWINSKA E.; WATRAS J.; WIDEL M., ACTA POL. PHARM., 1978, 35, NO 5, 529-535
  作者：SUWINSKI J.、 SALWINSKA E.、 WATRAS J.、 WIDEL M.

  DOI：——

  日期：——
• SUWINSKI J.; RAJCA A.; WATRAS J.; WIDEL M., ACTA POL. PHARM., 1980, 37, NO 1, 59-67
  作者：SUWINSKI J.、 RAJCA A.、 WATRAS J.、 WIDEL M.

  DOI：——

  日期：——
• TULECKI, J.;ZAPRUTKO, L., ACTA POL. PHARM., 1984, 41, N 3, 281-292
  作者：TULECKI, J.、ZAPRUTKO, L.

  DOI：——

  日期：——

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