Medicinal Chemistry of Hetrocyclic Compound

Medicinal Chemistry of Hetrocyclic Compound

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  Advance Organic Chemistry-1 Guidedby Prepared by Mr. Atul Hemke Ms. Puja Basule M- Pharm First Year (1st sem) Topic – Ketoconazole, Metronidazole, Terconazole & Miconazole Synthesis Department of P’ceutical Chemistry SKB College of Pharmacy 1
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  Contents • Metronidazole Introduction Synthesis Mechanism Properties& Uses  Ketoconazole & Terconazole Introduction Synthesis Mechanism Properties & Uses • Miconazole Introduction Synthesis Mechanism Properties & uses 2
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  Metronidazole • Metronidazole isa synthetic nitroimidazole antibiotic that acts againts anaerobic bacteria & some protozoa • Antiprotozoal & Antibacterial Activity • Metronidazole has a broad spectrum activity. It acts againts anaerobic bacteria and some protozoa as Amoeba & Giardia IUPAC Name:- 2-(2-Methyl-5-Nitro-1-yl)ethanol Molecular Formula:- C6H9N3O3 Molar Mass:- 171.156 g/mol-1 Melting Point:- 159 to 163OC 3
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  Mechanism of Action •Metronidazole (prodrug) enter • Aerobic & Anaerobic Bacteria (micro-organism) • Reduced to 5-nitro position (ferred oxins) • Produces number of short lived cytotoxic intermediates • Cytotoxic products react with DNA & other macromolecules (damage microbial DNA) • Cell Death 5
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  Properties • It isa white or crystalline powder • Slightly soluble in water, acetone, alcohol & methylene chloride. Uses • It is used in the treatment of intestinal & hepatic amoebiasis. 6
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  Ketoconazole • Ketoconazole belongsto the class of drug called Azole antifungal. • It work by stopping the growth of the fungus. • Ketoconazole should not be used to treat fungal infections on the skin and nails due to the risk of serious side effects & drug interaction. • IUPAC Name:- 1-[4-[4-[[2- 2,4-dichlorophenyl)-2-(imida zole -1-ylmethyl)-1,3-dioxola n-4-yl]methoxy]phenyl]piper azin-1-yl]ethanone • Molar mass:- 531.4g/mol • Formula:-C26H28CL2N4O4 7
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  Synthesis of Ketoconazole 8
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  Mechanism of Action •Inhibits an enzyme, resulting in cell wall leaking • Block demethylation of lanosterol to ergosterol • Leads to altered cell membrane (unstable) • Fungal cell death 9
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  Properties • ketonazole isa white powder • Pratically insoluble in water • Soluble in methylene chloride & in methanole • Sparingly soluble in alcohol Uses:- • It is used as antifungal agent 10
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  Miconazole • Meconazole isan antifungal synthetic derivative of Imidazole & use in the tratment of candidal Skin infection IUPAC Name:- 1-(2,4-dichlorophenyl)- 2-(imidazole-1-yl)ethanol Molecular Formula:- C18H14CL4N2O Molecular wt:- 461.1 g/mol Melting point:- 159-1630C 11
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  Synthesis of Miconazole 12
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  Mode of action •Inhibit an enzyme, resulting in cell membrane leaking • Lead to altered cell membrane • Finally fungal cell death 13
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  Properties • It isa white powder • Very slightly soluble in water & slightly soluble in alcohol • Sparingly soluble in methanol Uses:- • It is used as an Antifungal agent 14
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  Reference 1. Text bookof ‘Medicinal Chemistry’ “V.Alagarsamy” Third edition volume- 1 & 2 2. Text book of ‘Pharmacology’ “Triphati” sixth edition 15
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