Abstract
Purpose: To synthesize some alkyl derivatives of carbazole and evaluate their in vitro inhibitory effect on alpha amylase and alpha glucosidase. Methods : Synthesis of methylcarbazole, ethylcarbazole, propylcarbazole and butylcarbazole was carried out using acid-catalysed alkylation method while in vitro inhibitory assay on alpha amylase and alpha glucosidase enzymes on the synthesized compounds was evaluated using standard procedures. Acarbose was used as the reference compound. Results: For carbazole, methylcarbazole, ethylcarbazole, propylcarbazole and butylcarbazole, the IC 50 values of alpha amylase inhibitory assay were 87.47, 50.23, 47.20, 42.36 and 42.11 μg/mL respectively. IC 50 values of alpha glucosidase inhibitory assay for ethylcarbazole, propylcarbazole and butylcarbazole were 205.30, 153.93 and 152.90 μg/mL, respectively. Carbazole and methylcarbazole had no inhibitory effect on this enzyme but the reference drug (acarbose) had a better inhibitory effect towards the two enzymes than the synthesized products. Conclusion: Some alkyl-carbazoles with anti-diabetic effect have been successfully synthesised. Alkylation of carbazole increased the alpha amylase inhibitory effect of carbazole. The inhibitory effect is directly proportional to the chain length of the alkyl group. Keywords: Alkyl carbazole, alpha amylase, alpha glucosidase, synthesis
Highlights
Diabetes mellitus (DM) is a metabolic disorder [1] which is the fourth main cause of death in most developed countries and one of the leading causes of kidney failure, heart attack, blindness and lower limb amputation
Some carbazole derivatives are known to possess anticancer, antimicrobial, anti HIV, antihypertensive, antiparkinsonian, antipsychotic, anti-emetic and antidiabetic activities [6]. Some antidiabetic compounds such as tetrahydroalstonine, lochnerinine, vindoline, harmine, reserpine, vincanidine and vinervine obtained from plants have carbazole-like nucleus which may be essential to their antidiabetic activity
Acarbose was used as the reference alpha-amylase inhibitor and all tests were performed in triplicate
Summary
Diabetes mellitus (DM) is a metabolic disorder [1] which is the fourth main cause of death in most developed countries and one of the leading causes of kidney failure, heart attack, blindness and lower limb amputation. This work was undertaken to synthesise and test some alkyl-carbazole compounds for their antidiabetic activity by evaluating their inhibitory effects on alpha amylase and alpha glucosidase activities. This could provide a ‘lead’ to the discovery of novel antidiabetic drugs. The assay mixture containing 200 μL of 0.02 M sodium phosphate buffer, 20 μL of enzyme and the synthesized products in concentration range 20-100 μg/mL were incubated for 10 minutes at room temperature followed by addition of 200 μL of starch in all test tubes. Propylcarbazole: Rf, 0.65; (pH, 5.72); Melting points, 120-123oC; λmax in chloroform and absorbance (346.00 nm, 1.915); IR absorption: 3427.62 (N-H), 2925.15 (C-H Alkane (stretch)), 1642.44 (C=C (Aromatic)), 1461.43 (-CH2 (bend)), 1345.39 (-CH3 (bend)); Formula: C15H15N. Acarbose was used as the reference alpha-amylase inhibitor (positive control) and all tests were performed in triplicate
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