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Synthesis of sydnone substituted Biginelli derivatives as hyaluronidase inhibitors. 2013

Tegginamath Gireesh, and Ravindra R Kamble, and Pramod P Kattimani, and Atukuri Dorababu, and Maraswamy Manikantha, and Joy H Hoskeri
Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad, India.

A novel series of Biginelli 2-3 (a and b) and Biginelli-like compounds 4-7 (a and b) were synthesized from 3-aryl-4-formylsydnone 1 (a and b). Since the crystal structure of hyaluronidase was unavailable, the human hyaluronidase protein structure was used as template and homology modeling was performed, validated by Ramachandran plots and subjected to docking studies along with in vitro anti-inflammatory activity assessment against hyaluronidase. Compounds 2-3 (a and b) exhibited potent enzyme inhibition.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D010078 Oxazines Six-membered heterocycles containing an oxygen and a nitrogen.
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D006821 Hyaluronoglucosaminidase An enzyme that catalyzes the random hydrolysis of 1,4-linkages between N-acetyl-beta-D-glucosamine and D-glucuronate residues in hyaluronate. (From Enzyme Nomenclature, 1992) There has been use as ANTINEOPLASTIC AGENTS to limit NEOPLASM METASTASIS. Hyaluronidase,Duran-Reynals Permeability Factor,GL Enzyme,Hyaglosidase,Hyaluronate Hydrolase,Wydase,Duran Reynals Permeability Factor,Factor, Duran-Reynals Permeability,Hydrolase, Hyaluronate,Permeability Factor, Duran-Reynals
D000893 Anti-Inflammatory Agents Substances that reduce or suppress INFLAMMATION. Anti-Inflammatory Agent,Antiinflammatory Agent,Agents, Anti-Inflammatory,Agents, Antiinflammatory,Anti-Inflammatories,Antiinflammatories,Antiinflammatory Agents,Agent, Anti-Inflammatory,Agent, Antiinflammatory,Agents, Anti Inflammatory,Anti Inflammatories,Anti Inflammatory Agent,Anti Inflammatory Agents
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013558 Sydnones OXADIAZOLES bearing an oxygen at the 5-position. They are mesoionic, with delocalized positive and negative charges.
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs

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