Azoles, A Potential Anti Diabetic Agents as α- Glucosidase Inhibitors: Past, Current & Future Prospects
DOI:
https://doi.org/10.52783/jns.v14.1802Keywords:
Diabetes, α-Glucosidase inhibitors, Azole.Abstract
Diabetes is a chronic disordered metabolism disease, indicated by Elevated blood glucose level. Various methods such as Fasting plasma glucose level Oral glucose tolerance test (OGTT) and HbA1c test , have been used to diagnose elevated blood glucose level in the body. A better medication is the only solution to control this disease. For this at present, α-Glucosidase inhibitors are recently used as a first line drug with safer efficacy. During study many previous study it was found that various chemical moieties were involved in the synthesis of α-Glucosidase inhibitors for the treatment of diabetes. Compound bearing azole moiety were one of them. This article compiled various recent researches which involved various types of compounds, having azole in their structure. Our main objective of this article is to focus on such facts, which can be used to design and synthesis of α- Glucosidase inhibitors bearing azole moiety, related to, which will further direct to the researchers in future.
Downloads
Metrics
References
Hameed I, Masoodi SR, Mir SA, Nabi M, Ghazanfar K, Ganai BA. (2015) Type 2 diabetes mellitus: From a metabolic disorder to an inflammatory condition. World J Diabetes. 2015 May 15;6(4):598-612. doi: 10.4239/wjd.v6.i4.598.
American Diabetes Association. Diagnosis and classification of diabetes mellitus.2009 Diabetes Care. 32 Suppl 1(Suppl 1):S62-7. doi: 10.2337/dc09-S062.
Rahman MS, Hossain KS, Das S, Kundu S, Adegoke EO, Rahman MA, Hannan MA, Uddin MJ, Pang MG. (2021) Role of Insulin in Health and Disease: An Update. Int J Mol Sci. 15;22(12):6403. doi: 10.3390/ijms22126403.
Banday MZ, Sameer AS, Nissar S. (2020) Pathophysiology of diabetes: An overview. Avicenna J Med. Oct 13;10(4):174-188. doi: 10.4103/ajm.ajm_53_20.
Singh N, Kesherwani R, Tiwari AK, Patel DK (2016) A review on diabetes mellitus. J. Pharm. Innov. (7): 36-40.
Marsden J, Pickering D. (2015) Urine testing for diabetic analysis. Community Eye Health. 2015;28(92):77. PMID: 27418731; PMCID: PMC4944103.
Kaur G, Lakshmi PVM, Rastogi A, Bhansali A, Jain S, Teerawattananon Y, Bano H, Prinja S. (2020)Diagnostic accuracy of tests for type 2 diabetes and prediabetes: A systematic review and meta-analysis. PLoS One. 20;15(11):e0242415. doi: 10.1371/journal.pone.0242415.
Hieshima K, Sugiyama S, Yoshida A, Kurinami N, Suzuki T, Ijima H, Miyamoto F, Kajiwara K, Jinnouchi K, Jinnouchi T, Jinnouchi H. (2020) Elevation of the renal threshold for glucose is associated with insulin resistance and higher glycated hemoglobin levels. J Diabetes Investig. 2020 May;11(3):617-625. doi: 10.1111/jdi.13191. Epub 2020 Jan 15.
Mitrakou A, Kelley D, Mokan M, Veneman T, Pangburn T, Reilly J, Gerich J. (1992) Role of reduced suppression of glucose production and diminished early insulin release in impaired glucose tolerance. N Engl J Med. 2;326(1):22-9. doi: 10.1056/NEJM199201023260104.
Pasieka AM, Rafacho A. 2016 Impact of Glucocorticoid Excess on Glucose Tolerance: Clinical and Preclinical Evidence. Metabolites. 3;6(3):24. doi: 10.3390/metabo6030024.
Seager LH. (1965) Renal Glycosuria With a False-Positive Glucose Tolerance Test. JAMA. 193(5):392–393. doi:10.1001/jama.1965.03090050068024
International Diabetes Federation. IDF Diabetes Atlas. 6th ed. Brussels, Belgium: International Diabetes Federation; 2013. Available from: http://www.idf.org/diabetesatlas.
DiMeglio LA, Evans-Molina C, Oram RA. (2018) Type 1 diabetes. Lancet. 16;391(10138):2449-2462. doi: 10.1016/S0140-6736(18)31320-5.
Olokoba AB, Obateru OA, Olokoba LB. (2012) Type 2 diabetes mellitus: a review of current trends. Oman Med J. 27(4):269-73. doi: 10.5001/omj.2012.68.
Modzelewski R, Stefanowicz-Rutkowska MM, Matuszewski W, Bandurska-Stankiewicz EM. (2022) Gestational Diabetes Mellitus-Recent Literature Review. J Clin Med. 28;11(19):5736. doi: 10.3390/jcm11195736.
Kumar A, Gangwar R, Zargar AA, Kumar R, Sharma A (2024) Prevalence of Diabetes in India: A Review of IDF Diabetes Atlas 10th Edition. Curr Diabetes Rev. 20(1):e130423215752. doi: 10.2174/1573399819666230413094200.
Lebovitz HE. (1997) alpha-Glucosidase inhibitors. Endocrinol Metab Clin North Am. 26(3):539-51. doi: 10.1016/s0889-8529(05)70266-8.
Di Magno L, Di Pastena F, Bordone R, Coni S, Canettieri G. (2022) The Mechanism of Action of Biguanides: New Answers to a Complex Question. Cancers (Basel). 30;14(13):3220. doi: 10.3390/cancers14133220.
Sola D, Rossi L, Schianca GP, Maffioli P, Bigliocca M, Mella R, Corlianò F, Fra GP, Bartoli E, Derosa G. (2015) Sulfonylureas and their use in clinical practice. Arch Med Sci. 12;11(4):840-8. doi: 10.5114/aoms.2015.53304.
Lebovitz HE. Thiazolidinediones: the Forgotten Diabetes Medications. (2019)Curr Diab Rep. 27;19(12):151. doi: 10.1007/s11892-019-1270-y.
Florentin M, Kostapanos MS, Papazafiropoulou AK. (2022) Role of dipeptidyl peptidase 4 inhibitors in the new era of antidiabetic treatment. World J Diabetes. 15;13(2):85-96. doi: 10.4239/wjd.v13.i2.85.
Shah RB, Patel M, Maahs DM, Shah VN (2016) Insulin delivery methods: Past, present and future. Int J Pharm Investig. 6(1):1-9. doi: 10.4103/2230-973X.176456.
The World Health Report. Shaping the future, 2003.
Mishra V, Nayak P, Sharma M, Albutti A, Alwashmi ASS, Aljasir MA, Alsowayeh N, Tambuwala MM (2021) Emerging Treatment Strategies for Diabetes Mellitus and Associated Complications: An Update. Pharmaceutics. 27;13(10):1568. doi: 10.3390/pharmaceutics13101568.
Bowen R 2006 "Dietary Polysaccharides". Arbl.cvmbs.colostate. edu. http://www.vivo.colostate.edu/hbooks/pathphys/digestion/basics/polysac.html.
Barmak A. Niknam K. Gholamhossein MG (2019) Synthesis, Structural Studies, and α Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H) ones Derived from Pyrazol-4-carbaldehyde and Anilines” ACS Omega 4:18087-18099.
Assefa ST, Yang EY, Chae SY, Song M, Lee J, Cho MC, Jang S. (2019) Alpha Glucosidase Inhibitory Activities of Plants with Focus on Common Vegetables. Plants (Basel). 18;9(1):2. doi: 10.3390/plants9010002.
Liu Z Shutao M S. (2017) Recent Advances in Synthetic a-Glucosidase Inhibitors” Chem Med Chem, 12, 819-829.
Alqahtani AS, Hidayathulla S, Rehman MT, ElGamal AA, Al-Massarani S, Razmovski-Naumovski V, Alqahtani MS, El Dib RA, AlAjmi MF. Alpha-Amylase and Alpha-Glucosidase Enzyme Inhibition and Antioxidant Potential of 3-Oxolupenal and Katononic Acid Isolated from Nuxia oppositifolia. Biomolecules. 2019 Dec 30;10(1):61. doi: 10.3390/biom10010061.
Assefa ST, Yang EY, Chae SY, Song M, Lee J, Cho MC, Jang S. (2019) Alpha Glucosidase Inhibitory Activities of Plants with Focus on Common Vegetables. Plants (Basel). 18;9(1):2. doi: 10.3390/plants9010002.
Kashtoh H, Baek KH. (2022) Recent Updates on Phytoconstituent Alpha-Glucosidase Inhibitors: An Approach towards the Treatment of Type Two Diabetes. Plants (Basel). 14;11(20):2722. doi: 10.3390/plants11202722.
Derosa G Maffioli P. (2012) α-Glucosidase inhibitors and their use in clinical practice” Arch Med Sci 9;8(5); 899-906.
Hossain U, Das AK, Ghosh S, Sil PC. (2020)An overview on the role of bioactive α-glucosidase inhibitors in ameliorating diabetic complications. Food Chem Toxicol. 145:111738. doi: 10.1016/j.fct.2020.111738.
Sharma, R., Prasad Y, Mishra, GP, Chaturvedi, SC. (2013) Some substituted 1,3,4-thiadiazoles: a novel centrally acting agents. Medicinal Chemistry Research, DOI – 00044-013-626-0.
Ghani U. (2015) Re-exploring promising α-glucosidase inhibitors for potential development into oral anti-diabetic drugs: Finding needle in the haystack. Eur J Med Chem. 20;103:133-62. doi: 10.1016/j.ejmech.2015.08.043.
McIver LA, Preuss CV, Tripp J.(2024) Acarbose. 21. In: StatPearls [Internet]. Treasure Island (FL)–. PMID: 29630266.
Dabhi AS, Bhatt NR, Shah MJ. (2013) Voglibose: an alpha glucosidase inhibitor. J Clin Diagn Res. 7(12):3023-7. doi: 10.7860/JCDR/2013/6373.3838.
Sels JP, Huijberts MS, Wolffenbuttel BH. (1999) Miglitol, a new alpha-glucosidase inhibitor. Expert Opin Pharmacother. 1(1):149-56. doi: 10.1517/14656566.1.1.149.
Kuznetsov AE. (2021) Introductory Chapter: Azoles, Their Importance, and Applications. 1-8. doi: 10.5772/intechopen.98426
Mishra, GP, Sharma, R.(2015), Identification of potential PPAR-γ agonists as hypoglycemic agents: molecular docking approach. Interdisciplinary Sciences: Computational Life Sciences , 8(3), 220-8, doi:10.1007/s12539-015-0126-7.
Hussain R, Iqbal S, Shah M, Rehman W, Khan S, Rasheed L, Rahim F, Dera AA, Kehili S, Elkaeed EB (2022) Synthesis of Novel Benzimidazole-Based Thiazole Derivatives as Multipotent Inhibitors of α-Amylase and α-Glucosidase: In Vitro Evaluation along with Molecular Docking Study. Molecules 27(19):6457. doi:10.3390/molecules27196457
Javid MT, Rahim F, Taha M, Rehman HU, Nawaz M, Wadood A, Imran S, Uddin I, Mosaddik A, Khan KM (2018) Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs. Bioorg Chem. 78:201-209. doi: 10.1016/j.bioorg.2018.03.022.
Khan KM, Qurban S, Salar U, Taha M, Hussain S, Perveen S, Hameed A, Ismail NH, Riaz M, Wadood A. (2016) Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives. Bioorg Chem. 68:245-58. doi: 10.1016/j.bioorg.2016.08.010.
Nasli EA, Iraji A, Alamir A, Moradi S, Asgari MS, Hosseini S, Mojtabavi S, Nasli-Esfahani E, Faramarzi MA, Bandarian F, Larijani B, Hamedifar H, Hajimiri MH, Mahdavi M.( 2022)Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors. Mol Divers. 26(4):1995-2009. doi: 10.1007/s11030-021-10310-7.
Khan S, Iqbal S, Taha M, Hussain R, Rahim F, Shah M, Awwad NS, Ibrahium HA, Alahmdi MI, Dera AA, Ullah H, Bahadur A, Aljazzar SO, Elkaeed EB, Rauf M. (2023) Synthesis, in vitro biological assessment, and molecular docking study of benzimidazole-based thiadiazole derivatives as dual inhibitors of α-amylase and α-glucosidase. Front Chem. 5;11:1125915. doi: 10.3389/fchem.2023.1125915.
Zahra FT, Saeed A, Ahmed A, Ismail H, Ijaz MU, Albericio F (2023) Synthesis of amantadine clubbed N-aryl amino thiazoles as potent urease, α-amylase & α-glucosidase inhibitors, kinetic and molecular docking studies. RSC Adv. 22;13(36):24988-25001. doi: 10.1039/d3ra05330j.
Singh G, Singh A, Verma RK, Mall R, Azeem U. Synthesis (2018) biological evaluation and molecular docking studies of novel benzimidazole derivatives. Comput Biol Chem. 72:45-52. doi: 10.1016/j.compbiolchem.2017.12.010.
Mishra S, Dahima R. Sharma R. (2020) Synthesis and Biological Evaluation of Benzimidazoles as target for α- Glucosidase inhibitors J. Drug Deliv. Ther. 10(2-s), pp. 43-49. doi: 10.22270/jddt.v10i2-s.4019
Aroua LM, Almuhaylan HR, Alminderej FM, Messaoudi S, Chigurupati S, Al-Mahmoud S, Mohammed HA. (2021) A facile approach synthesis of benzoylaryl benzimidazole as potential α-amylase and α-glucosidase inhibitor with antioxidant activity. Bioorg Chem. 114:105073. doi: 10.1016/j.bioorg.2021.105073
Özil M, Emirik M, Etlik SY, Ülker S, Kahveci B. (2016) A simple and efficient synthesis of novel inhibitors of alpha-glucosidase based on benzimidazole skeleton and molecular docking studies. Bioorg Chem. 68:226-35. doi: 10.1016/j.bioorg.2016.08.011.
Z Zawawi NK, Taha M, Ahmat N, Wadood A, Ismail NH, Rahim F, Azam SS, Abdullah N. (2016) Benzimidazole derivatives as new α-glucosidase inhibitors and in silico studies. Bioorg Chem. 64:29-36. doi: 10.1016/j.bioorg.2015.11.006.
Nasli Esfahani A, Iraji A, Alamir A, Moradi S, Asgari MS, Hosseini S, Mojtabavi S, Nasli-Esfahani E, Faramarzi MA, Bandarian F, Larijani B, Hamedifar H, Hajimiri MH, Mahdavi M. (2022) Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors. Mol Divers. 26(4):1995-2009. doi: 10.1007/s11030-021-10310-7.
Dinparast L, Valizadeh H, Bahadori MB, Soltani S, Asghari B , Rashidi MR. 2016 Design, synthesis , a-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives” J. Mol. Struct.: 1114:84-94.
doi: 10.1016/j.molstruc.2016.02.005
Bharadwaj SS, Poojary B, Nandish SKM, Kengaiah J, Kirana MP, Shankar MK, Das AJ, Kulal A. Sannaningaiah D (2018) Efficient Synthesis and in Silico Studies of the Benzimidazole Hybrid Scaffold with the Quinolinyloxadiazole Skeleton with Potential α Glucosidase Inhibitory, Anticoagulant, and Antiplatelet Activities for Type-II Diabetes Mellitus Management and Treating Thrombotic Disorders” ACS Omega, 31:2562-12574. doi: 10.1021/acsomega.8b01476
Özil M, Emirik M, Beldüz A, Ülker S. (2016) Molecular docking studies and synthesis of novel bisbenzimidazole derivatives as inhibitors of α-glucosidase. Bioorg Med Chem. 1;24(21):5103-5114. doi: 10.1016/j.bmc.2016.08.024.
Kumar JA, Tiwari AK, Ali AZ, Madhusudhana K, Reddy BS, Ramakrishna S, China Raju B. (2010) New antihyperglycemic, alpha-glucosidase inhibitory, and cytotoxic derivatives of benzimidazoles. J Enzyme Inhib Med Chem. 25(1):80-6. doi: 10.3109/14756360903017122.
Yan L, Lui H, Sun J, Gao L, Lu X, Li X, Chen H. 2019 Synthesis of tricyclic benzimidazole-iminosugars as potential glycosidase inhibitors via a Mitsunobu reaction. Carbohydr Res. 1;485:107807. doi: 10.1016/j.carres.2019.107807.
Singh G, Singh A, Verma RK, Mall R. Azeem U (2018) Synthesis, biological evaluation and molecular docking studies of novel benzimidazole derivatives
Comput. Biol. Chem. 72: 45-52. doi: 10.1016/j.compbiolchem.2017.12.010
Arshad T, Khan KM, Rasool N, Salar U, Hussain S, Tahir T, Ashraf M, Wadood A, Riaz M, Perveen S, Taha M, Ismail NH. (2016) Syntheses, in vitro evaluation and molecular docking studies of 5-bromo-2-aryl benzimidazoles as α-glucosidase inhibitors, Med Chem Res. 25 : 2058-2069. doi: 10.1007/s00044-016-1614-y
Taha M, Ismail NH, Imran S, Mohamad MH, Wadood A, Rahim F, Saad SM, Rehman AU, Khan KM.(2016) Synthesis, α-glucosidase inhibitory, cytotoxicity and docking studies of 2-aryl-7-methylbenzimidazoles. Bioorg Chem. 65:100-9. doi: 10.1016/j.bioorg.2016.02.004.
Zawawi NK, Taha M, Ahmat N, Ismail NH, Wadood A, Rahim F. (2017) Synthesis, molecular docking studies of hybrid benzimidazole as α-glucosidase inhibitor. Bioorg Chem. 70:184-191. doi: 10.1016/j.bioorg.2016.12.009.
Ali M, Ali S, Khan M, Rashid U, Ahmad M, Khan A, Al-Harrasi A, Ullah F, Latif A. (2018) Synthesis, biological activities, and molecular docking studies of 2-mercaptobenzimidazole based derivatives. Bioorg Chem. 80:472-479. doi: 10.1016/j.bioorg.2018.06.032.
Downloads
Published
How to Cite
Issue
Section
License
This work is licensed under a Creative Commons Attribution 4.0 International License.
You are free to:
- Share — copy and redistribute the material in any medium or format
- Adapt — remix, transform, and build upon the material for any purpose, even commercially.
Terms:
- Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- No additional restrictions — You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.
