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SYNTHESIS OF SOME NICOTINIC ACID DERIVATIVES AS POTENTIAL THERAPEUTIC AGENTS AND EXTRACTION, ISOALTION OF ACTIVE COMPONENTS OF MOMORDICA CHARANTIA

Ahmed, Mansoor (1994) SYNTHESIS OF SOME NICOTINIC ACID DERIVATIVES AS POTENTIAL THERAPEUTIC AGENTS AND EXTRACTION, ISOALTION OF ACTIVE COMPONENTS OF MOMORDICA CHARANTIA. PhD thesis, University of Karachi, Karachi.

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Abstract

The work embodied in this thesis has been divided into two parts. The first part (Part-A) is entitled as Synthesis of Some Nicotinic Acid Derivatives as Potential Therapeutic Agents and the second part (Part-B) is related to the Extraction, Isolation of Active Components of Momordica charantia Part-A. This part of the thesis deals with the synthesis and structure activity relationship studies of nicotinic acid derivatives. As a result of these studies, synthesis of fourteen derivatives (III-XVI) of nicotinic acid series and thirteen derivatives (XVII-XXIX) of 5-bromonicotinic acid series has been achieved. The cytotoxicity (Table 1 and Table 6), antimicrobial activity (Table 2-3 and Table 7-8) and the effects on mean arterial blood pressure (Table 4-5 and Table 9-10) of these compounds has also been determined. All compounds are listed below: 1. 3-Carboxy-1-(4-methylphenacyl)-pyridinium bromide (III) 2. 3-Carboxy-1-(3-methylphenacyl)-pyridinium bromide (IV) 3. 3-Carboxy-1-(4-methylphenacyl)-pyridinium bromide (V) 4. 3-Carboxy-1-(2,4-dimethoxyphenacyl)-pyridinium bromide (VI) 5. 3-Carboxy-1-(2,5-dimethoxyphenacyl)-pyridinium bromide (VII) 6. 3-Carboxy-1-(3,5-dimethoxyphenacyl)-pyridinium chloride (VIII) 7. 3-Carboxy-1-(4-bromophenacyl)-pyridinium bromide (XI) 8. 3-Carboxy-1-(4-chlorophenacyl)-pyridinium bromide (X) 9. 3-Carboxy-1-(4-flulorophenacyl)-pyridinium chloride (XI) 10. 3-Carboxy-1-(2,4-difluorophenacyl)-pyridinium bromide (XII) 11. 3-Carboxy-1-(2-nitrophenacyl)-pyridinium bromide (XIII) 12. 3-Carboxy-1-(4-nitrophenacyl)-pyridinium bromide (XIV) 13. 3-Carboxy-1-(4-phenylphenacyl)-pyridinium bromide (XV) 14. 3-Carboxy-1-(1-adamantyl methyl ketone)-pyridinium bromide (XVI) 15. 3-Carboxy-1-(4-methylphenacyl)-5-bromopyridinium bromide (XVII) 16. 3-Carboxy-1-(3-methylphenacyl)-5-bromopyridinium bromide (XVIII) 17. 3-Carboxy-1-(4-methoxyphenacyl)-5-bromopyridinium bromide (XIX) 18. 3-Carboxy-1-(2,4-dimethoxyphenacyl)-5-bromopyridinium bromide (XX) 19. 3-Carboxy-1-(2-dimethoxyphenacyl)-5-bromopyridinium bromide (XXI) 20. 3-Carboxy-1-(3,4-dihythroxyphenacyl)-5-bromopyridinium bromide (XXII) 21. 3-Carboxy-1-(4-bromophenacyl)-5-bromopyridinium bromide (XXIII) 22. 3-Carboxy-1-(4-chlorophenacyl)-5-bromopyridinium bromide (XXIV) 23. 3-Carboxy-1-(4-fluorophenacyl)-5-bromopyridinium chloride (XXV) 24. 3-Carboxy-1-(2-nitrophenacyl)-5-bromopyridinium bromide (XXVI) 25. 3-Carboxy-1-(4-nitrophenacyl)-5-bromopyridinium bromide (XXVII) 26. 3-Carboxy-1-(4-phenylphenacyl)-5-bromopyridinium bromide (XXVIII) 27. 3-Carboxy-1-(1-adamantyl methyl ketone)-5-bromopyridinium bromide (XXIX) Part-B The second part is related to natural product chemistry. The isolation and structure elucidation of the chemical constituents of Momoridica charantia which is known for its pharmacological significance has been included in Part-B. The neutral fraction obtained on work-up (Scheme-1) of the methanolic extract of the fresh and undried fruits of Momoridica charantia (Cucurbitaceae) was subjected to chemical investigations, which led to the isolation of five compounds (I-V which are noted below. 1. 13-Hydroxy-3-keto-28-methoxy-11-ursene (I) 2. 13,28-Epoxy-3-keto-11-ursene (II) 3. 24-[1-Hydroxystigmasta-5-14-dien-16-one (IV) 4. 3-Hydroxystigmasta-5-14-dien-16-one (IV) 5. 6[1(9,10,11,19,20-Pentamethyl)-5,13,15,18-tetraol]-6-cyclohexenone (V) The structure elucidation of compounds noted in part-A and B involved various spectroscopic techniques such as UV, IR, EIMS, HRMS, FDMS, FABMS, 1H-NMR. The introduction of part-A and B provides a review of the earlier contribution made in the chemistry and pharmacology of nicotinic acid its derivatives and the genus Momoradica

Item Type:Thesis (PhD)
Uncontrolled Keywords:nicotinic acid, therapeutic agents, momordica charantia, 5-bromonicotinic acid
Subjects:Physical Sciences (f) > Chemistry(f2)
ID Code:1103
Deposited By:Mr. Muhammad Asif
Deposited On:20 Dec 2006
Last Modified:04 Oct 2007 21:04

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