奥硝唑异构体 | 14419-11-5

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 奥硝唑异构体
• 中文别名: 奥硝唑杂质H；1-氯-3-(2-甲基-4-硝基-1H-咪唑-1-基)丙烷-2-醇；奥硝唑异构体
• 英文名称: (±)-1-chloro-3-(2-methyl-4-nitro-1H-imidazol-1-yl)propan-2-ol
• 英文别名: 1-(3-chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole；1-[3-chloro-2-hydroxypropyl]-2-methyl-4-nitroimidazole；1-(3-Chlor-2-hydroxypropyl)-2-methyl-4-nitroimidazol；1-chloro-3-(2-methyl-4-nitro-imidazol-1-yl)-propan-2-ol；1-(2-Hydroxy-3-chlor-propyl)-2-methyl-4-nitro-imidazol；1-chloro-3-(2-methyl-4-nitroimidazol-1-yl)propan-2-ol
• CAS: 14419-11-5
• 化学式: C₇H₁₀ClN₃O₃
• 分子量: 219.628
• InChiKey: JCFLTWHMNZZBFW-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C
• 沸点：
  443.2±40.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  4

制备方法与用途

用途

本品为奥硝唑的一种异构体杂质，具备抗感染特性。

反应信息

• 作为反应物：
  描述：

  奥硝唑异构体 在 sodium hydroxide 、 pyridinium polyhydrogenfluoride 作用下， 反应 12.25h， 生成 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：

  2-甲基-4-硝基咪唑 、 环氧氯丙烷 在 aluminum (III) chloride 作用下， 以 乙酸乙酯 为溶剂， 以5.6 g的产率得到奥硝唑异构体
  参考文献：
  名称：

  一种2-甲基-4-硝基咪唑衍生物及其制备方法和药用组合物的用途

  摘要：

  本发明提供了2‑甲基‑4‑硝基咪唑的衍生物，发明还提供了2‑甲基‑4‑硝基咪唑衍生物的制备方法。另外，含2‑甲基‑4‑硝基咪唑的衍生物的药物组合物被应用于治疗由脆弱拟杆菌、狄氏拟杆菌、卵园拟杆菌、多形拟杆菌、普通拟杆菌、梭状芽胞杆菌、真杆菌、消化球菌和消化链球菌、幽门螺杆菌、黑色素拟杆菌、梭杆菌、CO2噬织维菌、牙龈类杆菌等敏感厌氧菌所引起的多种感染性疾病。

  公开号：

  CN107235911A

文献信息

• 2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas : Design, synthesis, biology and 3D-QSAR study
  作者：Dhanaraju Mandalapu、Bhavana Kushwaha、Sonal Gupta、Nidhi Singh、Mahendra Shukla、Jitendra Kumar、Dilip K. Tanpula、Satya N. Sankhwar、Jagdamba P. Maikhuri、Mohammad I. Siddiqi、Jawahar Lal、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.ejmech.2016.09.006

  日期：2016.11

  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.
• Senczuk, Lidia; Taczalska, Danuta, Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1055 - 1057
  作者：Senczuk, Lidia、Taczalska, Danuta

  DOI：——

  日期：——
• 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：——