A STUDY ON EFFECT OF INDOLE AS A SUBSTITUENT ON A KETO-ENOL TAUTOMER: A SYNTHETIC APPROACH ON β-DIKETONE
Journal Title: International Journal of Pharmacy and Pharmaceutical Sciences - Year 2017, Vol 9, Issue 8
Abstract
Objective: The existence of keto-enol tautomerism in β-diketones can typically study by a choice of analytical technique. The position of the keto-enol equilibrium depends on a number of factors like solvent, temperature, and substituents. Here an attempt was made to examine the effect of indole, a heterocyclic moiety with the moderately high polar surface area to examine its effect on ketonisation of β-diketone.Methods: The β-diketone studied and synthesized is a structural analog of magical drug curcumin. The structural influence of indole on ketonisation of β-diketone is studied to give a hypothesis on factors contributing towards ketonisation. This work involves the synthesis of 6-(1H-Indol-3-yl)-hex-5ene-2, 4-dione and the study on the single crystal structure of indole-3-carboxaldehyde, major functional component to result in the reaction. The tautomer was studied for its ability to bind with tetrahydrofolate reductase enzyme using Discovery Studio 3.5 version to differentiate the pharmacological significance of conformations.Results: The single crystal XRD structure of this compound was deposited in Cambridge crystallographic data center bearing CCDC No.1536311. The structural characterization of synthesized ligand was carried out by using IR, Mass, 1H NMR spectroscopic techniques. The docking study reveals that keto isomer found to exhibit more inhibition of the enzyme tetrahydrofolate reductase hence more pharmacologically active.Conclusion: The experimental evidence proves that indole substitution shifted the keto-enol equilibrium towards keto form of 6-(1H-Indol-3-yl)-hex-5ene-2, 4-dione.
Authors and Affiliations
Krishnakumar K. L. , Mathew Paul Ukken, Manju R.
Keywords
Related Articles
- EP ID EP575583
- DOI 10.22159/ijpps.2017v9i8.19576
- Views 90
- Downloads 0
CHARACTERISATION OF CAROTENOID CONTENT IN DIVERSE LOCAL SWEET POTATO (IPOMOEA BATATAS) FLESH TUBERS
Sweet potato (Ipomoea batatas) is one of the most important food crops in the world. Sweet potato is rich with carotenoids and pro-vitamin A. Carotenoids compounds are commonly found in fruits and vegetables and are res...
ANTI-INFLAMMATORY STUDIES IN RELATION TO CHEMICAL EVALUATION ON TWO SPECIES OF AN INDIGENOUS DRUG ‘BARLERIA’
Objective: The present study was aimed to assess the anti-inflammatory activity profile of Barleria spp. viz., B. prionitis Linn. and B. cristata Linn. against different models of inflammation in female rats.Methods: Sev...
ANTI-ULCER STUDY OF STANDARDIZED ETHANOL ROOT EXTRACT OF AGANOSMA DICHOTOMA AND ISOLATED URSOLIC ACID
Objective: Aganosma dichotoma K. Schum (Apocynaceae) has been traditionally used as an Ayurvedic ulcer treatment and the study scientifically validates the antiulcer effect of A. dichotoma ethanol root extract (EAD).Meth...
FORMULATION AND ASSESSMENT OF A HERBAL HAIR CREAM AGAINST CERTAIN DERMATOPHYTES
Objective: Developing an herbal antifungal formulation containing eruca and garlic oils against highly resistant dermatophytes (Malassezia fufur AUMC No. 5173, Microsporum canis bodin AUMC No. 5490 and Trichophyton menta...
ANALYSIS OF PRESCRIPTION INDICATORS FOR OUTPATIENTS WITH HEALTH INSURANCE IN OUTPATIENTS DEPARTMENT AT CAN THO UNIVERSITY OF MEDICINE AND PHARMACY HOSPITAL IN THE PERIOD 2017-2018
Objective: The main objective of this study was to evaluate the drug prescription parameters and to find out the elements had an influence on the prescribing practice of doctors’. Methods: A descriptive cross-sectional...