2,3-diphenylquinoxaline-7-sulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-diphenylquinoxaline-7-sulfonamide
• 英文别名: 2,3-Diphenylquinoxaline-6-sulfonamide
• 化学式: C₂₀H₁₅N₃O₂S
• 分子量: 361.424
• InChiKey: ZRFIKPZSJCAIRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 樟脑 、 2,3-diphenylquinoxaline-7-sulfonamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以62.9%的产率得到2,3-diphenyl-7-((4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptan-2-yl)methyl) quinoxaline-6-sulfonamide
  参考文献：
  名称：

  New camphor hybrids: lipophilic enhancement improves antimicrobial efficacy against drug-resistant pathogenic microbes and intestinal worms

  摘要：

  Using the Blanc reaction, new derivatives of camphor (1a-g) and camphor sulfonic acid (2a-g) were synthesized. Chemical structures of the new derivatives were supported by IR, H-1-NMR, C-13-NMR, and LC-MS/MS (ESI) spectrometric analyses. The new compounds (1a-g/2a-g) and the parent compounds (a-g) were tested for their antimicrobial efficacy against the following drug-resistant pathogens: methicillin-resistant Staphylococcus aureus (MRSA), multi-drug resistant Klebsiella pneumonia (MDR-Kb), Escherichia coli (FDA control), Acinetobacter baumannii, Pseudomonas aeruginosa, Candida albicans (CLSI: Clinical and Laboratory Standards Institute strain) and Cryptococcus neoformans var. grubii. The linking of camphor to quinoxalin-2,3(1H, 4H)-dione (1a) enhances the antibacterial efficacy approximately 8-folds (MIC: 24 A mu M) against MRSA. Camphor linking with isatin (1g) increased efficacy against Acinetobacter baumannii by 8-fold (MIC: 26 A mu M) and by 4-fold (MIC: 51 A mu M) against MRSA, MDR-Kb, E. coli, P. auruginosa and C. albicans. Among the series, derivatives of benzoin (1e) and salicylic acid (1f) exhibited greater efficacy against drug-resistant Candida albicans, MDR-Kb and Acinetobacter baumannii, whereas 6, 7-biphenylquinoxalin 2-sulfonamide/sulphonyl chloride (1b/1d) selectively inhibited the growth of Gram-negative bacteria. None of these compounds were active against Cryptococcus neoformans var. grubii. Furthermore, these new derivatives were tested for anthelmintic efficacy and the results indicated that new compounds had significant anthelmintic efficacy (p < 0.05) at 2.5 mg/mL, except for the salicylic acid hybrids (1f, 2f). To conclude, camphor hybrids (1a-g) demonstrated enhanced antimicrobial and anthelmintic efficacy compared to the camphor sulfonic acid hybrids (2a-g). This improved antimicrobial efficacy may be due to the increased membrane permeability of the compounds across the cell wall, via the camphor moiety, which augmented the lipophilicity of the new compounds.

  DOI：

  10.1007/s00044-018-2186-9

文献信息

• New camphor hybrids: lipophilic enhancement improves antimicrobial efficacy against drug-resistant pathogenic microbes and intestinal worms
  作者：Ramalingam Peraman、Amit K. Tiwari、M. Geetha Vani、J. Hemanth、Y. Geetha Sree、K. Karthik、Charles R. Ashby、Y. Padmanabha Reddy、Raghuveer V. Pemmidi

  DOI：10.1007/s00044-018-2186-9

  日期：2018.6

  Using the Blanc reaction, new derivatives of camphor (1a-g) and camphor sulfonic acid (2a-g) were synthesized. Chemical structures of the new derivatives were supported by IR, H-1-NMR, C-13-NMR, and LC-MS/MS (ESI) spectrometric analyses. The new compounds (1a-g/2a-g) and the parent compounds (a-g) were tested for their antimicrobial efficacy against the following drug-resistant pathogens: methicillin-resistant Staphylococcus aureus (MRSA), multi-drug resistant Klebsiella pneumonia (MDR-Kb), Escherichia coli (FDA control), Acinetobacter baumannii, Pseudomonas aeruginosa, Candida albicans (CLSI: Clinical and Laboratory Standards Institute strain) and Cryptococcus neoformans var. grubii. The linking of camphor to quinoxalin-2,3(1H, 4H)-dione (1a) enhances the antibacterial efficacy approximately 8-folds (MIC: 24 A mu M) against MRSA. Camphor linking with isatin (1g) increased efficacy against Acinetobacter baumannii by 8-fold (MIC: 26 A mu M) and by 4-fold (MIC: 51 A mu M) against MRSA, MDR-Kb, E. coli, P. auruginosa and C. albicans. Among the series, derivatives of benzoin (1e) and salicylic acid (1f) exhibited greater efficacy against drug-resistant Candida albicans, MDR-Kb and Acinetobacter baumannii, whereas 6, 7-biphenylquinoxalin 2-sulfonamide/sulphonyl chloride (1b/1d) selectively inhibited the growth of Gram-negative bacteria. None of these compounds were active against Cryptococcus neoformans var. grubii. Furthermore, these new derivatives were tested for anthelmintic efficacy and the results indicated that new compounds had significant anthelmintic efficacy (p < 0.05) at 2.5 mg/mL, except for the salicylic acid hybrids (1f, 2f). To conclude, camphor hybrids (1a-g) demonstrated enhanced antimicrobial and anthelmintic efficacy compared to the camphor sulfonic acid hybrids (2a-g). This improved antimicrobial efficacy may be due to the increased membrane permeability of the compounds across the cell wall, via the camphor moiety, which augmented the lipophilicity of the new compounds.