2-methyl-5-nitro-1-[2-(phenylthio)ethyl]-1H-imidazole | 54252-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-5-nitro-1-[2-(phenylthio)ethyl]-1H-imidazole
• 英文别名: 1-(2-Phenylthioethyl)-5-nitro-2-methylimidazol；2-methyl-5-nitro-1-(2-phenylsulfanyl-ethyl)-1H-imidazole；2-methyl-5-nitro-1-(2-phenylsulfanylethyl)imidazole
• CAS: 54252-00-5
• 化学式: C₁₂H₁₃N₃O₂S
• 分子量: 263.32
• InChiKey: IZAHTJKIRJEVEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-5-nitro-1-[2-(phenylthio)ethyl]-1H-imidazole 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 1-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]-4,5-diphenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis and biological activity of new metronidazole derivatives

  摘要：

  The development of new antimicrobial and antiparasitic agents offers the possibility of generating structures of increased potency. To this end, three sulphonate ester derivatives of metronidazole were synthesized. Treatment of the tosylate analogue with NaSPh and NaN3 gave the thiophenolate and azide derivatives, respectively. Oxidation of phenylthio derivative with mCPBA afforded the sulfonyl analogue. Similarly, cycloaddition of azido-metronidazole with various symmetric acetylene compounds furnished the 1,2,3-triazole analogues. Treatment of dimethyl dicarboxylate metronidazole derivative with guanidine hydrochloride in the presence of base resulted in the formation of the ring-expanded (fat) derivative, triazolo-diazepam derivative of metronidazole. Treatment of chlorometronidazole with silylated quinolones gave the quinolone analogues of metronidazole. The antigardiasis and antifungal activities of the synthesized compounds were investigated. In addition, all synthesized compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors.[GRAPHICS].

  DOI：

  10.1007/s00706-015-1612-7
• 作为产物：
  描述：

  甲硝唑 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-methyl-5-nitro-1-[2-(phenylthio)ethyl]-1H-imidazole
  参考文献：
  名称：

  Synthesis and biological activity of new metronidazole derivatives

  摘要：

  The development of new antimicrobial and antiparasitic agents offers the possibility of generating structures of increased potency. To this end, three sulphonate ester derivatives of metronidazole were synthesized. Treatment of the tosylate analogue with NaSPh and NaN3 gave the thiophenolate and azide derivatives, respectively. Oxidation of phenylthio derivative with mCPBA afforded the sulfonyl analogue. Similarly, cycloaddition of azido-metronidazole with various symmetric acetylene compounds furnished the 1,2,3-triazole analogues. Treatment of dimethyl dicarboxylate metronidazole derivative with guanidine hydrochloride in the presence of base resulted in the formation of the ring-expanded (fat) derivative, triazolo-diazepam derivative of metronidazole. Treatment of chlorometronidazole with silylated quinolones gave the quinolone analogues of metronidazole. The antigardiasis and antifungal activities of the synthesized compounds were investigated. In addition, all synthesized compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors.[GRAPHICS].

  DOI：

  10.1007/s00706-015-1612-7

文献信息

• US3828065A
  申请人：——

  公开号：US3828065A

  公开（公告）日：1974-08-06