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 105
- Downloads 0
ANTIMICROBIAL POTENTIALOF HEMOLYMPH AND HEPATOPANCREAS OFPORTUNUSSEGNISCRABS
Objective: The potential of marine crabs as a source of bioactive products is largely unexplored. Methods: Portunussegnis crabs were collected from the northern coast of Persian Gulf. Antimicrobial activities of hepatopa...
PHARMACOGNOSTIC AND PHYTOCHEMICAL STUDIES OF CASSIA ABSUS SEED EXTRACTS
Objective: To carry out the pharmacognostic and phytochemical analysis of different extracts of seeds of Cassia absus (CA).Methods: The CA plant material (seeds) was studied for its organoleptic, microscopic and physicoc...
IN-VITRO DISSOLUTION STUDY OF MELOXICAM IMMEDIATE RELEASE PRODUCTS USING FLOW THROUGH CELL (USP APPARATUS 4) UNDER DIFFERENT OPERATIONAL CONDITIONS
Objective: To evaluate and compare the in-vitro dissolution profiles of five generic immediate release (IR) products of Meloxicam (MX) available in Egyptian market with the innovator reference product (Mobic®, R) using...
CLOUD POINT EXTRACTION, PRECONCENRATION AND SPECTROPHOTOMETRIC DETERMINATION OF COBALT IN WATER SAMPLES
Objective: A new cloud point extraction (CPE) method was developed for pre concentration of trace cobalt (II) in water samples.Methods: The method is based on the complexation reaction of Co (II) with 2-(benzothiazolyl a...
COMBINATIONAL EFFECTS OF ETHYLACETATE EXTRACT OF PICRIA FEL-TERRAE LOUR AND DOXORUBICIN ON T47D BREAST CANCER CELLS
Objective: To evaluate the effects of ethyl acetate extract (EAE) of Picria fel-terrae Lour. Leaves and combination with doxorubicin on cytotoxicity, cell cycle, apoptotis and suppression of cyclin D1 and Bcl-2 express...