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Abstract

DESIGN AND CNS STIMULATION SCREENING OF (2E)-1,3,7- TRIMETHYL-2-{[(2R)-2-(PYRIDIN-3-YL)PYRROLIDIN-1- YL]METHYLIDENE}-1,2,3,7-TETRAHYDRO-6H-PURIN-6-ONE BY SEMI SYNTHESISED NOVEL MOIETY OF NATURAL PRODUCT PURINE WITH PYRIDINE–PYRROLIDINE NUCLEUS

Piyush A. Gediya* and Dr. Dhrubo Jyoti Sen

Postgraduate Research Laboratory, Department of Pharmaceutical Chemistry, Shri Sarvajanik Pharmacy College, Gujarat Technological University, Arvind Baug, Mehsana–384001, Gujarat, India.

ABSTRACT

Semisynthetic design of natural products Caffeine and Nicotine adduct has been innovated by reacting the both plant extract moieties to generate Caffeine-Nicotine adduct on their functional groups. Caffeine has free carbonyl group which has been conjugated with free methyl group of nicotine to get an alkene bridge by removal of H2O. Caffeine has two carbonyl functional groups: one is in between two nitrogen atoms and another is in between one nitrogen and one carbon atom. Nitrogen atom has one lone pair of electrons, so the carbonyl group in between two nitrogen atoms is activated by electronegativity of nitrogen which is 3.1 for two nitrogen atoms 2×3.1=6.2 over the electronegativity of oxygen which is 3.5. So the methyl group of nicotine acts on that carbonyl group which is in between two nitrogen atoms rather than another and the desired moiety is generated by elimination of one mole of H2O. UV spectra of Caffeine, Nicotine and Adduct shows remarkable bathochromic peak shift by Caffeine: λmax 275nm, Nicotine: λmax 343nm and Adduct: λmax 336nm. Caffeine: 275nmCaffeine: – 0.13>Adduct: –1.01. Both of the plant extracts have CNS stimulating property, so the idea has been innovated to make the adduct of caffeine–nicotine moiety to screen the CNS stimulating property of individual extracts and adduct by rota rod apparatus with pentylenetetrazol as reference standard. CNS stimulation study has been done by recording muscle coordination time which showed good response in caffeine and in adduct but in adduct showed the synergistic action of the both Caffeine+Nicotine.

Keywords: Caffeine, Nicotine, Solid–Liquid extraction, Liquid–Liquid extraction, Caffeine– Nicotine adduct, Rota rod apparatus, CNS stimulation, Pentylenetetrazol.


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