Synthesis, Characterization and Antidiabetic Activity of Novel Thiazolidine Derivatives
DOI:
https://doi.org/10.37285/ijpsn.2018.11.1.5Abstract
Rhodamines are five-member heterocyclic having nitrogen and sulphur atoms in their ring structure respectively and exhibiting potent as well as wide range of pharmacological activities. A series of 4-((4-oxo-2-thioxothiazolidin-5-ylidene) methyl) phenyl substituted benzoate derivatives were synthesized. Benzoic acid derivatives reacted with rhodanine to yield the respective derivatives. This reaction follows the Knoevenagel condensation reaction mechanism by which ethanolamine abstract a proton from heterocyclic ring and a carbanion ion is generated. The structure of synthesize compounds were supported by IR, NMR and mass spectral data. The synthesized compounds were screened for their in vitro antidiabetic activity by α-Amylase, α-Glucosidase inhibition, glucose diffusion inhibitory test and the potential compounds tested for in vivo activity by blood glucose and body weight changes, serum insulin, Hb, HbA1c, and total protein levels changes, and lipid profiles changes in type 2 diabetic rats.
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Keywords:
Hydantoin, Rhodanine, Knoevenagel condensation, Thiazolidines, Antidiabetic
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Published
2018-01-31
How to Cite
1.
Prachand S, Gupta AK, Gilhotra R. Synthesis, Characterization and Antidiabetic Activity of Novel Thiazolidine Derivatives. Scopus Indexed [Internet]. 2018 Jan. 31 [cited 2024 May 18];11(1):3977-83. Available from: http://www.ijpsnonline.com/index.php/ijpsn/article/view/350
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Research Articles
References
Bloomgarden ZT (1999). American Diabetes Association Annual Meeting New Approaches to Insulin treatment and Glucose Monitoring. Diabetes Care 22: 2078-2082.
Brenner GM and Stevens CW (2006). Pharmacology. Philadelphia, Pa, USA: Saunders.
Calisti L and Tognetti S (2005). Measure of glycosylated hemoglobin. Acta Biomedica de l’AteneoParmense 76(3): 59-62.
Castaneda C (2002). Muscle wasting and protein metabolism. J Animal Sci 80(2): E98-E105.
Deguchi Y and Miyazaki K (2010). Anti-hyperglycemic and anti-hyperlipidemic effects of guava leaf extract. Nutrition Metabol 7(9): 1-10.
Denise MF and David K (2000). GSK-3: New thoughts on an old enzyme. Dev Biol 225: 471-479.
Fabbro D, Manley PW, Jahnke W, Liebetanz J, Szyttenholm A, Fendrich G, Strauss A, Zhang J, Gray NS, Adrian F, Warmuth M, Pelle X, Grotzfeld R, Berst F, Marzinzik A, Cowan-Jacob SW, Furet P, Mestan J (2010). Inhibitors of the Abl kinase directed at either the ATP or myristate-binding site. Biochim Biophys Acta 1804(3): 454-62 (doi: 10.1016/j bbapap 2009.12.009).
Dewanjee S, Das AK, Sahu R and Gangopadhyay M (2009). Antidiabetic activity of Diospyrosperegrina fruit: effect on hyperglycemia, hyperlipidemia and augmented oxidative stress in experimental type 2 diabetes. Food ChemToxicol 47(10): 2679-2685.
Frame S and Philip C (2001). GSK3 takes center stage more than 20 years after its discovery.Biochem J 359: 1-16.
Garuti L, Roberti M and Bottegoni G (2010). Non-ATP competitive protein kinase inhibitors. Curr Med Chem 17(25): 2804-21.
Gray AM and Flatt PR (1997). Nature’s own pharmacy: The diabetes perspective. Proc Nutr Soc 56: 507- 517.
Gualandi-Signorini AM and Giorgi G (2001). Insulin Formulations -A Review. European Review for Medical and Pharmacological Sciences 5: 73-83.
Gurudeeban S, Satyavani K and Ramanathan T (2012). Alpha glucosidase inhibitory effect and enzyme kinetics of coastal medicinal plants. Bangladesh J Pharmacol; 7:186-191.
Ibrahim SS and Rizk SM (2002). Nicotinamide: a cytoprotectant against streptozotocin induced diabetic damage in Wistar rat brains. African J Biochem Res 2(8): 174-180.
International Diabetes Federation, IDF Diabetes Atlas, 5th edition, 2013, http://www.idf.org/diabetesatlas/5e/the-global-burden.
Jayasri MA, Radha A and Mathew TL (2009). α-amylase and α- glucosidase inhibitory activity of Costuspictus D Don in the management of diabetes. J Herbal Med Toxicol 3(1): 91-94.
Kuppusamy A, Muthusamy U, Andichetiar Thirumalaisamy S, Varadharajan S, Ramasamy K and Ramanathan S (2011). In vitro (α-glucosidase and α-amylase inhibition) and in vivo antidiabetic property of phytic acid (IP6) in streptozotocin-nicotinamide induced type 2 diabetes mellitus (NIDDM) in rats. J Complement Integrative Med8 (1, article 9).
Khanfar AM, Bilal AA, Mudit M, Kaddoumi A and Khalid AE (2009). The marine natural-derived inhibitors of glycogen synthase kinase-3β phenylmethylenehydantoins: In vitro and in vivo activities and pharmacophore modeling. Bioorg Med Chem 17: 6032-6039
Krentz AJ and Bailey CJ (2005). Oral Antidiabetic Agents: Current Role in Type 2 Diabetes Mellitus. Drugs 65 (3): 385-411
Kumar EK and Janardhana GRJ (2011). Antidiabetic activity of alcoholic stem extract of Nerviliaplicata in streptozotocin-nicotinamide induced type 2 diabetic rats. Ethnopharmacol 133(2): 480-3.
Mahomoodally MF, Subratty AH, Gurib-Fakim A, Choudary MI, and Khan SN (2012). Traditional medicinal herbs and food plants have the potential to inhibit key carbohydrates hydrolyzing enzymes in vitro and reduce postprandial blood glucose peaks in vivo. The Scientific World Journal.
Mayur B, Sandesh S, Shruti S and Sung-Yum S (2010). Antioxidant and α-glucosidase inhibitory properties of Carpesium abrotanoides L. J Med Plants Res 4:1547-1553.
Meanwell NA (2011). Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem Res Toxicol 24(9): 1420-56. doi: 10.1021/tx200211v
Meijer L, Flajolet M and Greengard P (2004). Pharmacological inhibitors of glycogen synthase kinase 3. Trends Pharmacol Sci 25(9) doi:10.1016/j.tips.2004.07.006
Ministry of Health and Quality of life (MOH) (2009). The trends in diabetes and cardiovascular disease risk in Mauritius The Mauritius Non Communicable Disease Survey
Miwa I, Hirano M, Inagaki K, Belbeoc'h C and Okuda J (1987). Development of Potent Aldose Reductase Inhibitors Having a Hydantoin Structure. Biochem Pharmacol 36(17): 2789-2794
Miwa I, Inagaki K, Yashiro T and Okuda J (1984). Hypoglycemic Activity of Aldose Reductase Inhibitor, 1-[(P-Bromophenyl) sulfonyl]hydantoin. Chem Pharm Bull 32(5): 2030-2032.
Mochida E, Murakami K, Kato K, Okuda J and Miwa I.Hydantoin derivatives for use as hypoglycemic and/or hypolipidemic agents, European patent no EP 0444546 B1 . Application number: 91102632.6
Mooradian AD (2009). Dyslipidemia in type 2 diabetes mellitus. Nat ClinPrac Endocrinol Metabol 5(3): 150-159.
Mylari BL. Metformin derivatives for treating diabetes and diabetes complications. US Patent no US 8853259 B2
Pasupathi P, Chandrasekar V and Kumar US (2009). Evaluation of oxidative stress, enzymatic and non-enzymatic antioxidants and metabolic thyroid hormone status in patients with diabetes mellitus. Diabetes and Metabolic Syndrome: Clinical Research & Reviews 3(3):160-165.
Pennathur S and Heinecke JW (2004). Mechanisms of oxidative stress in diabetes: implications for the pathogenesis of vascular disease and antioxidant therapy. Frontiers in Bioscience 9: 565-574.
Rhabasa-Lhoret R and Chiasson JL (2004). Alpha-glucosidase inhibition In: International Textbook of Diabetes Mellitus Defronzo RA, Ferrannini E, Keen H, Zimmet P (Ed) pp. 901-914 John Wiley & Sons, London, UK.
Sanger F (1959). Chemistry of Insulin. Science129: 1340-1343.
Brenner GM and Stevens CW (2006). Pharmacology. Philadelphia, Pa, USA: Saunders.
Calisti L and Tognetti S (2005). Measure of glycosylated hemoglobin. Acta Biomedica de l’AteneoParmense 76(3): 59-62.
Castaneda C (2002). Muscle wasting and protein metabolism. J Animal Sci 80(2): E98-E105.
Deguchi Y and Miyazaki K (2010). Anti-hyperglycemic and anti-hyperlipidemic effects of guava leaf extract. Nutrition Metabol 7(9): 1-10.
Denise MF and David K (2000). GSK-3: New thoughts on an old enzyme. Dev Biol 225: 471-479.
Fabbro D, Manley PW, Jahnke W, Liebetanz J, Szyttenholm A, Fendrich G, Strauss A, Zhang J, Gray NS, Adrian F, Warmuth M, Pelle X, Grotzfeld R, Berst F, Marzinzik A, Cowan-Jacob SW, Furet P, Mestan J (2010). Inhibitors of the Abl kinase directed at either the ATP or myristate-binding site. Biochim Biophys Acta 1804(3): 454-62 (doi: 10.1016/j bbapap 2009.12.009).
Dewanjee S, Das AK, Sahu R and Gangopadhyay M (2009). Antidiabetic activity of Diospyrosperegrina fruit: effect on hyperglycemia, hyperlipidemia and augmented oxidative stress in experimental type 2 diabetes. Food ChemToxicol 47(10): 2679-2685.
Frame S and Philip C (2001). GSK3 takes center stage more than 20 years after its discovery.Biochem J 359: 1-16.
Garuti L, Roberti M and Bottegoni G (2010). Non-ATP competitive protein kinase inhibitors. Curr Med Chem 17(25): 2804-21.
Gray AM and Flatt PR (1997). Nature’s own pharmacy: The diabetes perspective. Proc Nutr Soc 56: 507- 517.
Gualandi-Signorini AM and Giorgi G (2001). Insulin Formulations -A Review. European Review for Medical and Pharmacological Sciences 5: 73-83.
Gurudeeban S, Satyavani K and Ramanathan T (2012). Alpha glucosidase inhibitory effect and enzyme kinetics of coastal medicinal plants. Bangladesh J Pharmacol; 7:186-191.
Ibrahim SS and Rizk SM (2002). Nicotinamide: a cytoprotectant against streptozotocin induced diabetic damage in Wistar rat brains. African J Biochem Res 2(8): 174-180.
International Diabetes Federation, IDF Diabetes Atlas, 5th edition, 2013, http://www.idf.org/diabetesatlas/5e/the-global-burden.
Jayasri MA, Radha A and Mathew TL (2009). α-amylase and α- glucosidase inhibitory activity of Costuspictus D Don in the management of diabetes. J Herbal Med Toxicol 3(1): 91-94.
Kuppusamy A, Muthusamy U, Andichetiar Thirumalaisamy S, Varadharajan S, Ramasamy K and Ramanathan S (2011). In vitro (α-glucosidase and α-amylase inhibition) and in vivo antidiabetic property of phytic acid (IP6) in streptozotocin-nicotinamide induced type 2 diabetes mellitus (NIDDM) in rats. J Complement Integrative Med8 (1, article 9).
Khanfar AM, Bilal AA, Mudit M, Kaddoumi A and Khalid AE (2009). The marine natural-derived inhibitors of glycogen synthase kinase-3β phenylmethylenehydantoins: In vitro and in vivo activities and pharmacophore modeling. Bioorg Med Chem 17: 6032-6039
Krentz AJ and Bailey CJ (2005). Oral Antidiabetic Agents: Current Role in Type 2 Diabetes Mellitus. Drugs 65 (3): 385-411
Kumar EK and Janardhana GRJ (2011). Antidiabetic activity of alcoholic stem extract of Nerviliaplicata in streptozotocin-nicotinamide induced type 2 diabetic rats. Ethnopharmacol 133(2): 480-3.
Mahomoodally MF, Subratty AH, Gurib-Fakim A, Choudary MI, and Khan SN (2012). Traditional medicinal herbs and food plants have the potential to inhibit key carbohydrates hydrolyzing enzymes in vitro and reduce postprandial blood glucose peaks in vivo. The Scientific World Journal.
Mayur B, Sandesh S, Shruti S and Sung-Yum S (2010). Antioxidant and α-glucosidase inhibitory properties of Carpesium abrotanoides L. J Med Plants Res 4:1547-1553.
Meanwell NA (2011). Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem Res Toxicol 24(9): 1420-56. doi: 10.1021/tx200211v
Meijer L, Flajolet M and Greengard P (2004). Pharmacological inhibitors of glycogen synthase kinase 3. Trends Pharmacol Sci 25(9) doi:10.1016/j.tips.2004.07.006
Ministry of Health and Quality of life (MOH) (2009). The trends in diabetes and cardiovascular disease risk in Mauritius The Mauritius Non Communicable Disease Survey
Miwa I, Hirano M, Inagaki K, Belbeoc'h C and Okuda J (1987). Development of Potent Aldose Reductase Inhibitors Having a Hydantoin Structure. Biochem Pharmacol 36(17): 2789-2794
Miwa I, Inagaki K, Yashiro T and Okuda J (1984). Hypoglycemic Activity of Aldose Reductase Inhibitor, 1-[(P-Bromophenyl) sulfonyl]hydantoin. Chem Pharm Bull 32(5): 2030-2032.
Mochida E, Murakami K, Kato K, Okuda J and Miwa I.Hydantoin derivatives for use as hypoglycemic and/or hypolipidemic agents, European patent no EP 0444546 B1 . Application number: 91102632.6
Mooradian AD (2009). Dyslipidemia in type 2 diabetes mellitus. Nat ClinPrac Endocrinol Metabol 5(3): 150-159.
Mylari BL. Metformin derivatives for treating diabetes and diabetes complications. US Patent no US 8853259 B2
Pasupathi P, Chandrasekar V and Kumar US (2009). Evaluation of oxidative stress, enzymatic and non-enzymatic antioxidants and metabolic thyroid hormone status in patients with diabetes mellitus. Diabetes and Metabolic Syndrome: Clinical Research & Reviews 3(3):160-165.
Pennathur S and Heinecke JW (2004). Mechanisms of oxidative stress in diabetes: implications for the pathogenesis of vascular disease and antioxidant therapy. Frontiers in Bioscience 9: 565-574.
Rhabasa-Lhoret R and Chiasson JL (2004). Alpha-glucosidase inhibition In: International Textbook of Diabetes Mellitus Defronzo RA, Ferrannini E, Keen H, Zimmet P (Ed) pp. 901-914 John Wiley & Sons, London, UK.
Sanger F (1959). Chemistry of Insulin. Science129: 1340-1343.
