2-methyl-5-nitro-1-[2-(phenylsulfonyl)ethyl]-1H-imidazole | 28795-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-5-nitro-1-[2-(phenylsulfonyl)ethyl]-1H-imidazole
• 英文别名: 1-[2-(benzenesulfonyl)ethyl]-2-methyl-5-nitroimidazole
• CAS: 28795-25-7
• 化学式: C₁₂H₁₃N₃O₄S
• 分子量: 295.319
• InChiKey: WZDZCMPMOJPCIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 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：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-5-nitro-1-[2-(phenylsulfonyl)ethyl]-1H-imidazole 在 potassium fluoride on basic alumina 作用下， 以 乙二醇乙醚 为溶剂， 反应 0.25h， 以95%的产率得到1-[2-(Benzenesulfonyl)ethyl]-2-methyl-4-nitroimidazole
  参考文献：
  名称：

  氧化铝上的氟化钾——一种高效的 N-[2-(烷基/芳基磺酰基)乙基]-2-甲基-5-硝基-1H-咪唑异构化试剂

  摘要：

  摘要 KF/Al2O3 已被发现是一种有效的试剂，可用于将 1-[2-(烷基/芳基磺酰基)乙基]-2-甲基-5-硝基-1H-咪唑纯异构化为相应的 4-硝基异构体。 90% 的收率。

  DOI：

  10.1080/00397919108016768
• 作为产物：
  描述：

  甲硝唑 在 吡啶 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-methyl-5-nitro-1-[2-(phenylsulfonyl)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

• Rao, A. K. S. Bhujanga; Prasad, Ramanujam S.; Rao, C. Gundu, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1352 - 1353
  作者：Rao, A. K. S. Bhujanga、Prasad, Ramanujam S.、Rao, C. Gundu、Singh, Bajrang B.

  DOI：——

  日期：——
• RAO, A. K. S. BHUJANGA;GUNDU, RAO C.;SINGH, B. B., SYNTH. COMMUN., 21,(1991) N, C. 443-448
  作者：RAO, A. K. S. BHUJANGA、GUNDU, RAO C.、SINGH, B. B.

  DOI：——

  日期：——
• Synthesis and biological activity of new metronidazole derivatives
  作者：Najim A. Al-Masoudi、Zina A. A. Abbas

  DOI：10.1007/s00706-015-1612-7

  日期：2016.2

  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].
• Potassium Fluoride on Alumina—An Efficient Reagent for Isomerization of N-[2-(Alkyl/Arylsulfonyl)Ethyl]-2-Methyl-5-Nitro-1H-Imidazoles
  作者：A. K. S. Bhujanga Rao、C. Gundu Rao、B. B. Singh

  DOI：10.1080/00397919108016768

  日期：1991.2

  Abstract KF/Al2O3 has been found to be an efficient reagent for a neat isomerization of 1-[2-(Alkyl/Arylsulphonyl)ethyl]-2-methyl-5-nitro-1H-imidazoles to the corresponding 4-nitroisomers in more than 90% yields.

  摘要 KF/Al2O3 已被发现是一种有效的试剂，可用于将 1-[2-(烷基/芳基磺酰基)乙基]-2-甲基-5-硝基-1H-咪唑纯异构化为相应的 4-硝基异构体。 90% 的收率。