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One pot synthesis and SAR of some novel 3-substituted 5,6-diphenyl-1,2,4-triazines as antifungal agents. 2010

Jaiprakash N Sangshetti, and Devanand B Shinde
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431 004 (MS), India.

An improved protocol for the synthesis of a novel series of 1,2,4-triazines possessing 1,2,3-triazole and piperidine ring using 1-(1-substituted piperidin-4-yl)-1H-1,2,3-triazole-4-carbohydrazide, benzil, ammonium acetate and ZrOCl(2).8H(2)O as a catalyst in ethanol-water has been presented. The yields obtained are in the range of 87-94%. All the synthesized compounds (4a-4l) are novel and were evaluated for their in vitro antifungal activity. SAR for the series has been developed by comparing their MIC values with miconazole and fluconazole. Based on activity data SAR for the series has been developed. Compound 4c from the series was equipotent to miconazole against Candida albicans (MIC-25), Aspergillus niger (MIC-12.5) and Cryptococcus neoformans (MIC-25). Compound 4d was equipotent with miconazole against all tested organisms except Cryptococcus neoformans. Also compound 4i was equipotent with miconazole against C. albicans, A. niger and Fusarium oxysporum.

UI MeSH Term Description Entries
D008825 Miconazole An imidazole antifungal agent that is used topically and by intravenous infusion. Brentan,Dactarin,Miconasil Nitrate,Miconazole Nitrate,Monistat,R-14,889,Nitrate, Miconasil,Nitrate, Miconazole,R 14,889,R14,889
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D010880 Piperidines A family of hexahydropyridines.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics
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
D014227 Triazines Heterocyclic rings containing three nitrogen atoms, commonly in 1,2,4 or 1,3,5 or 2,4,6 formats. Some are used as HERBICIDES. Triazine,Benzotriazines
D015040 Zirconium A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.
D015725 Fluconazole Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS. Apo-Fluconazole,Béagyne,Diflucan,Fluc Hexal,FlucoLich,Flucobeta,Fluconazol AL,Fluconazol AbZ,Fluconazol Stada,Fluconazol von ct,Fluconazol-Isis,Fluconazol-ratiopharm,Flunazul,Fungata,Lavisa,Loitin,Neofomiral,Oxifungol,Solacap,Triflucan,UK-49858,Zonal,Apo Fluconazole,Fluconazol Isis,Fluconazol ratiopharm,UK 49858,UK49858

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