N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)benzamide | 86029-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)benzamide
• CAS: 86029-44-9
• 化学式: C₉H₈N₄O₃S₂
• 分子量: 284.32
• InChiKey: PMNNJWNEWDGYIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  benzoylamino-[1,3,4]thiadiazole-2-sulfonyl chloride 在 氨 作用下， 生成 N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)benzamide
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Treatment of chronic inflammatory joint disease with arylsulfonamides
  申请人：A. H. Robins Company, Incorporated

  公开号：US04990523A1

  公开（公告）日：1991-02-05

  A method of treating chronic inflammatory joint disease with arylsulfonamides of the formula: Z--SO.sub.2 NR.sup.1 R.sup.2 wherein R.sup.1 and R.sup.2 are selected from hydrogen, lower alkyl, lower alkenyl, cycloalkyl, phenyl, loweralkylphenyl, 2 or 3 pyrrolidinyl, 2 or 3-(N-loweralkylpyrrolidinyl, or R.sup.1 and R.sup.2 taken together may form pyrrolidinyl or piperidinyl heterocyclic amino radicals and Z is an aryl group selected from substituted or unsubstituted tetrazole, 1,3,4-thiadiazole, 1,2,4-triazole, benzothiazole, benzimidazole, imidazole, pyridyl, 4,6-dimethyl pyrimidine, benzene or naphthalene is disclosed.

  公开了一种使用以下结构的芳基磺酰胺来治疗慢性炎性关节疾病的方法：Z--SO.sub.2 NR.sup.1 R.sup.2其中R.sup.1和R.sup.2从氢、低烷基、低烯基、环烷基、苯基、低烷基苯基、2或3吡咯基、2或3-(N-低烷基吡咯基中选择，或者R.sup.1和R.sup.2一起可以形成吡咯基或哌啶基杂环氨基基团，Z是从取代或未取代的四唑基、1,3,4-噻二唑基、1,2,4-三唑基、苯并噻唑基、苯并咪唑基、咪唑基、吡啶基、4,6-二甲基嘧啶基、苯或萘中选择的芳基。
• [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。
• SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME
  申请人：Board of Regents, The University of Texas System

  公开号：US20130184317A1

  公开（公告）日：2013-07-18

  Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.

  本文描述了结合Pleckstrin同源结构域的化合物、包括此类化合物的制药组合物以及使用它们的方法。
• Acetazolamide-based fungal chitinase inhibitors
  作者：Alexander W. Schüttelkopf、Ludovic Gros、David E. Blair、Julie A. Frearson、Daan M.F. van Aalten、Ian H. Gilbert

  DOI：10.1016/j.bmc.2010.09.062

  日期：2010.12

  Chitin is an essential structural component of the fungal cell wall. Chitinases are thought to be important for fungal cell wall remodelling, and inhibition of these enzymes has been proposed as a potential strategy for development of novel anti-fungals. The fungal pathogen Aspergillus fumigatus possesses two distinct multi-gene chitinase families. Here we explore acetazolamide as a chemical scaffold for the inhibition of an A. fumigatus 'plant-type' chitinase. A co-crystal structure of AfChiA1 with acetazolamide was used to guide synthesis and screening of acetazolamide analogues that yielded SAR in agreement with these structural data. Although acetazolamide and its analogues are weak inhibitors of the enzyme, they have a high ligand efficiency and as such are interesting leads for future inhibitor development.
• 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.