N-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)acetamide | 98143-01-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)acetamide
• 英文别名: Methyl 5-acetamido-1,3,4-thiadiazol-2-yl sulfone；N-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)acetamide
• CAS: 98143-01-2
• 化学式: C₅H₇N₃O₃S₂
• mdl: MFCD18078471
• 分子量: 221.261
• InChiKey: CNOKSWHGWDXNSY-UHFFFAOYSA-N

物化性质

• 熔点：
  247-248 °C(Solv: water (7732-18-5))
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(5-甲硫基-1,3,4-噻二唑-2-基)乙酰胺 在 水 、 氯 、 三氯化铁 作用下， 生成 N-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)acetamide
  参考文献：
  名称：

  Pala, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 650,661

  摘要：

  DOI：

文献信息

• [EN] CARBONIC ANHYDRASE INHIBITORS AND ANTIBIOTICS AGAINST MULTIDRUG RESISTANT BACTERIA<br/>[FR] INHIBITEURS D'ANHYDRASE CARBONIQUE ET ANTIBIOTIQUES CONTRE DES BACTÉRIES MULTIRÉSISTANTES
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2020131980A1

  公开（公告）日：2020-06-25

  The invention described herein generally relates to novel therapeutic compounds, and in particular to carbonic anhydrase inhibitors as a narrow spectrum antibiotics against drug resistant bacteria and methods for treating those infection diseases in mammals using the described carbonic anhydrase inhibitors or a pharmaceutical formulation thereof.

  本发明通常涉及新型治疗化合物，特别是作为一种针对耐药细菌的窄谱抗生素的碳酸酐酶抑制剂，以及使用所述碳酸酐酶抑制剂或其制药配方治疗哺乳动物感染疾病的方法。
• Optimization of Acetazolamide-Based Scaffold as Potent Inhibitors of Vancomycin-Resistant <i>Enterococcus</i>
  作者：Jatinder Kaur、Xufeng Cao、Nader S. Abutaleb、Ahmed Elkashif、Amanda L. Graboski、Aaron D. Krabill、Ahmed Hassan AbdelKhalek、Weiwei An、Atul Bhardwaj、Mohamed N. Seleem、Daniel P. Flaherty

  DOI：10.1021/acs.jmedchem.0c00734

  日期：2020.9.10

  Vancomycin-resistant enterococci (VRE) are the second leading cause of hospital-acquired infections (HAIs) attributed to a drug-resistant bacterium in the United States, and resistance to the frontline treatments is well documented. To combat VRE, we have repurposed the FDA-approved carbonic anhydrase drug acetazolamide to design potent antienterococcal agents. Through structure-activity relationship optimization we have arrived at two leads possessing improved potency against clinical VRE strains from MIC = 2 mu g/mL (acetazolamide) to MIC = 0.007 mu g/mL (22) and 1 mu g/mL (26). Physicochemical properties were modified to design leads that have either high oral bioavailability to treat systemic infections or low intestinal permeability to treat VRE infections in the gastrointestinal tract. Our data suggest the intracellular targets for the molecules are putative alpha-carbonic and gamma-carbonic anhydrases, and homology modeling and molecular dynamics simulations were performed. Together, this study presents potential anti-VRE therapeutic options to provide alternatives for problematic VRE infections.
• Pala, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 650,661
  作者：Pala

  DOI：——

  日期：——