2,3-diphenylquinoxaline-6-sulfonyl chloride | 1429780-68-6

• 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-6-sulfonyl chloride
• 英文别名: 2,3-diphenylquinoxalin-7-sulphonylchloride；2,3-diphenylquinoxaline-6-sulfonylchloride
• CAS: 1429780-68-6
• 化学式: C₂₀H₁₃ClN₂O₂S
• 分子量: 380.854
• InChiKey: SHSIIKCYGOPOMF-UHFFFAOYSA-N

物化性质

• 沸点：
  523.5±45.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-diphenylquinoxaline-6-sulfonyl chloride 在 吡啶 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (Z)-N-(2-((4-hydroxybenzylidene)amino)phenyl)-2,3-diphenylquinoxaline-6-sulfonamide
  参考文献：
  名称：

  新型 N-(2-氨基苯基)-2,3- 二苯基喹喔啉-6-磺酰胺衍生物靶向 SARS-CoV-2 尖峰糖蛋白的受体结合域 (RBD) 的设计、合成和计算机模拟研究及其作为抗菌和抗疟药

  摘要：

  背景：由新型冠状病毒（SARS-CoV-2）引起的肺炎被命名为 2019 冠状病毒病（COVID-19）。SARS-CoV-2刺突糖蛋白的受体结合域（RBD）通过与人血管紧张素转换酶-2（hACE-2）结合，导致病毒侵入宿主细胞，从而导致进一步感染。 目的：设计并合成了新型 N-(2-氨基苯基)-2,3-二苯基喹喔啉-6-磺酰胺衍生物，通过分子对接工具抑制 SARS-CoV-2 刺突糖蛋白的 RBD。 方法：合成产物用红外光谱（IR）和1H核磁共振（NMR）表征。 结果：发现所有衍生物在 -9 至 -10.1 kcal/mol 之间具有非常好的结合亲和力，优于正在研究的用于治疗 SARS-CoV-2 感染的药物。化合物 F1 形成了 4 个氢键，而 F4 和 F10 分别与 SARS-CoV-2 刺突糖蛋白的 RBD 形成了两个氢键。所有衍生物均具有抗微生物、抗真菌和抗疟药敏感性。 结论：根据上述结果，我们得出结论，新型

  DOI：

  10.2174/1570180818666210427095203
• 作为产物：
  描述：

  邻苯二胺 在 氯磺酸 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2,3-diphenylquinoxaline-6-sulfonyl chloride
  参考文献：
  名称：

  新型 N-(2-氨基苯基)-2,3- 二苯基喹喔啉-6-磺酰胺衍生物靶向 SARS-CoV-2 尖峰糖蛋白的受体结合域 (RBD) 的设计、合成和计算机模拟研究及其作为抗菌和抗疟药

  摘要：

  背景：由新型冠状病毒（SARS-CoV-2）引起的肺炎被命名为 2019 冠状病毒病（COVID-19）。SARS-CoV-2刺突糖蛋白的受体结合域（RBD）通过与人血管紧张素转换酶-2（hACE-2）结合，导致病毒侵入宿主细胞，从而导致进一步感染。 目的：设计并合成了新型 N-(2-氨基苯基)-2,3-二苯基喹喔啉-6-磺酰胺衍生物，通过分子对接工具抑制 SARS-CoV-2 刺突糖蛋白的 RBD。 方法：合成产物用红外光谱（IR）和1H核磁共振（NMR）表征。 结果：发现所有衍生物在 -9 至 -10.1 kcal/mol 之间具有非常好的结合亲和力，优于正在研究的用于治疗 SARS-CoV-2 感染的药物。化合物 F1 形成了 4 个氢键，而 F4 和 F10 分别与 SARS-CoV-2 刺突糖蛋白的 RBD 形成了两个氢键。所有衍生物均具有抗微生物、抗真菌和抗疟药敏感性。 结论：根据上述结果，我们得出结论，新型

  DOI：

  10.2174/1570180818666210427095203

文献信息

• Sulphonamido-quinoxalines: Search for anticancer agent
  作者：Rahul Ingle、Rajendra Marathe、Dipak Magar、Harun M. Patel、Sanjay J. Surana

  DOI：10.1016/j.ejmech.2013.04.028

  日期：2013.7

  A series of new sulphonamido-quinoxaline derivatives 3(a-p) have been prepared which are structurally similar to the High Throughput Screening (HTS) hit identified by Porter and collaborator. The newly synthesized compounds 3b, 3c, 3f, 3i, 3j, 3l, 3n and 3o were further evaluated in the National Cancer Institute for in vitro cytotoxicity assay among them compound 3l showed highest activity against Leukemia RPMI-8226 cell lines (GI(50): 1.11 mu M) as compared to other tested compounds. It is to be noted that compound 31 shows significant activity (GI(50): 1.11 mu M) compared to the High Throughput Screening (HTS) hit identified by Porter and collaborator (IC50 = 1.3 mu M). Further docking study confirms the c-Met kinase inhibitory mechanism of the synthesized compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 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.
• Apoptotic impact on Brugia malayi by sulphonamido-quinoxaline: search for a novel therapeutic rationale
  作者：Priyanka S. Bhoj、Rahul G. Ingle、Kalyan Goswami、Lingaraj Jena、Shailesh Wadher

  DOI：10.1007/s00436-018-5834-6

  日期：2018.5

  Human lymphatic filariasis although not fatal but poses serious socioeconomic burden due to associated disability. This is reflected by the huge magnitude of the estimated disability-adjusted life years of about 5.09 million. Therefore, following WHO mandate, our earlier studies on antifilarial drug development revealed the significance of apoptosis. Apoptotic impact has been implicated in anticancer rationale of several drugs. In this study, we explored the antifilarial potential of sulphonamido-quinoxaline compounds, shown to be specific inhibitor for c-Met kinase in human cancer cells. Out of studied compounds, Q4, showing favorable drug-likeness and medicinal chemistry properties on bioinformatics platform along with subsequently recorded lowest IC100 value, was considered as a suitable antifilarial candidate. Significant apoptosis due to mitochondrial involvement was recorded in drug-treated parasite unlike untreated control. In spite of homology between human c-Met kinase and Brugia malayi counterpart, comparative docking result of this compound showed more favorable binding parameters with the parasitic target. The wide gap between IC100 and LD50 values further confirmed the therapeutic safety. We propose sulphonamido-quinoxaline derivative as a lead candidate for antifilarial drug development. Further study is warranted to authenticate parasitic c-Met kinase as a novel therapeutic target reminiscent of anticancer rationale implicating inhibition of proliferation.