(±)-2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 4-phenylpiperazine-1-carbodithioate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (±)-2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 4-phenylpiperazine-1-carbodithioate
• 英文别名: [2-Hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl] 4-phenylpiperazine-1-carbodithioate
• 化学式: C₁₈H₂₃N₅O₃S₂
• 分子量: 421.544
• InChiKey: GPSMDFWLIMFNAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  奥硝唑 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.5h， 生成 (±)-2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 4-phenylpiperazine-1-carbodithioate
  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

• 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents
  作者：Nur Sibel Günay、Gültaze Çapan、Nuray Ulusoy、Nedime Ergenç、Gülten Ötük、Dilek Kaya

  DOI：10.1016/s0014-827x(99)00109-3

  日期：1999.11

  Some novel 1-[2-[[5-(2-furanyl)-4-substituted 4H-1,2,4-triazol-3-yl]thio]ethyl]-2-methyl-5-nitro-1H-imidazoles (3), 1-[3-[[5-(2-furanyl/2-thienyl)-4-substituted 4H-1,2,4-triazol-3-yl]-thio]-2-hydroxypropyl]-2-methyl-5-nitro-1H-imidazoles (5) and 1-[3-[(N,N-disubstituted thiocarbamoyl)-thio]-2-hydroxypropyl]-2-methyl-5-nitro-1H-imidazoles (7) were synthesized and evaluated for in vitro antibacterial and antifungal activity. Some of 5 were found to be effective against bacteria and fungi (minimum inhibitory concentration (MIC) 7.3-125 mu g/ml), whereas 7 were found to be effective against fungi (MIC 3-25 mu g/ml). (C) 1999 Elsevier Science S.A. AII rights reserved.
• 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.