Open Access
Subscription Access
Open Access
Subscription Access
Synthesis of Some Novel Barbital Derivatives Based on Carbohydrate as α-Glucosidase Inhibitors
Subscribe/Renew Journal
A series of heterocyclic compounds were synthesized by reaction barbital derivatives with monosaccharaides derivatives. The structures of the prepared derivatives were identification by many spectroscopic methods including FTIR, 1H NMR, 13C NMR and Mass spectroscopy. The α-glucosidase inhibitory activities and antibacterial activities of some synthesized compounds were determination in vitro. All end compounds were showed α-glucosidase inhibitory activity in the range of (IC50 = 48.39 ±3.32–162.91±1.8μM) against the α-glucosidase enzyme when compared to the standard drug acarbose (IC50 = 787.27 ± 2.23 μM). Compounds 1t,2t,3t,4t and 5t showed significant α-glucosidase inhibitory activity with IC50 values of (162.91±1.8, 132.62±1.42, 68.44±2.11, 149.56±0.98, 48.39 ±3.32μM) respectively which were stronger than the positive controls acarbose. Compounds 5t and 3t have relatively higher therapeutic indices, representing potential promising leads. Overall result suggests that barbiturates with both five membered heterocyclic ring and monosaccharaides moiety could be lead a new design in the search of novel α-glucosidase inhibitor. Antibacterial activities of the synthesized compounds was screened against Escherichia coli and Staphylococcus aureus, using Azithromycin as reference.
Keywords
Barbital, 1,2,3-Triazole, Teterazole, Antibacterial Activity and α-Glucosidase Inhibitors.
Subscription
Login to verify subscription
User
Font Size
Information
- Roglic, G., World Health Organization. Global report on diabetes, Geneva, Switzerland, World Health Organization, 2016.
- Kleinberger, J.W., Pollin, T.I., Ann, N.Y., Personalized medicine in diabetes mellitus: current opportunities and future prospects, Acad. Sci., 2015,1346,45–56.
- Del Cueto, J., Møller, B.L., Dicenta, F., Sánchez-Pérez R., β-Glucosidase activity in almond seeds, Plant Physiol Biochem., 2018,126,163-172.
- Naureen, S., Chaudhry, F., Munawar, M.A., Ashraf, M., Hamid, S., Khan, M. Biological evaluation of new imidazole derivatives tethered with indole moiety as potent α-glucosidase inhibitors, Bioorganic Chemistry., 2018, 76, 365-369.
- Wang, G., Chen, M., Qiu, J., Xie, Z., Cao, A., Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives, Bioorganic Med Chem Lett., 2018,28,113-116.
- Miao, J.,; Li, X.,; Zhao, C., Gao, X., Wang, Y., Gao, W., Active compounds, antioxidant activity and α-glucosidase inhibitory activity of different varieties of Chaenomeles fruits, Food Chem., 2018,248,330-339.
- Anastasiou E, Lorentz KO, Stein GJ, Mitchell PD., Prehistoric schistosomiasis parasite found in the Middle East, Lancet Infect Dis, 2014,14,553-554.
- Ishikawa, F., Jinno, K., Kinouchi, E., Ninomiya, K., Marumoto, S., Xie, W.,Muraoka, O., Morikawa, T., Tanabe, G., Diastereoselective Synthesis of Salacinol-Type α-Glucosidase Inhibitors, J Org Chem., 2018, 83,185-193.
- Hollander, P., Safety profile of acarbose, an a-glucosidase inhibitor, Drugs 1992,44,47–53.
- Scott, L.J., Spencer, C.M., Miglitol: A review of its therapeutics potential in type 2 diabetes mellitus, Drug, 2000, 59,521-549.
- Jiancong, X., Xuliang, N., Yanping, H., Yan, J., Guoqiang, W., Xiaoli, Y., Chunrong, W., Xiaoqiang, W., Synthesis of water soluble glycosides of pentacyclic dihydroxytriterpene carboxylic acids as inhibitors of α-glucosidase, Carbohydrate Research, 2016,424,42–53.
- Singh, P., Verma, M.K., Design, synthesis and anticancer activities of hybrids of indole and barbituric acids—Identification of highly promising leads, Bioorg. Med. Chem. Lett., 2009,19,3054-3059.
- Barakat, A., Al-Majid, A.M., Al-Najjar, H.J., Mabkhot, Y.N., Javaid, S., Yousuf, S., Choudhary, M.I., Zwitterionic pyrimidinium adducts as antioxidants with therapeutic potential as nitric oxide scavenger, Eur. J. Med. Chem., 2014,84,146-151.
- Khan, K.M., Ali, M., Ajaz, A., Perveen, S., Choudhary, M.I., Synthesis of 5-arylidene barbiturates: A novel class of DPPH redical scavengers, Lett. In Drug Des. and Disc, 2008, 5(4), 286-291.
- Kolev, T., Bakalska, R., Seidel, R.W., Mayer-Figge, H.,Oppel, I.M., Spiteller, M., Sheldrick, W.S., Koleva, B.B., Novel codeinone derivatives via Michael addition of barbituric acids, Tetrahedron: Asymmetry, 2009,20,327–334.
- Penthala, N.R., Ponugoti, P.R., Kasam, V., Crooks., 5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties, Bioorganic & medicinal chemistry letters, 2013,23,1442-1446.
- Reddy, Y.T., Sekhar K.R., Sasi, N., Reddy, P.N., Freeman, M.L., Crooks, P.A., Antiangiogenic properties of substituted (Z)-(±)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-ol/one analogs and their derivatives, Bioorganic & medicinal chemistry letters, 2010, 20, 7323-7326.
- Chen, Z., Cai, D., Mou, D., Yan, Q., Sun, Y., Pan, W., Wan, Y., Song, H., Yi, W., Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors, Bioorganic & Medicinal Chemistry, 2014, 22,3279- 3284.
- Undriyal, S., Viswanad, B., Poduri, R., Chakraborti, A.K., Bharatam, P.V. New PPARc ligands based on barbituric acid: virtual screening, synthesis and receptor binding studies, Bioorg. Med.Chem. Lett., 2008,18,4959–4962.
- Joanna,K., Jacek, L., Hydroxyalkyl derivatives of 5,5-diethylbarbituric acid, Heterocyclic Communications, 2008, 14,199-204.
- Adnan, I. M., Rasha S. J., Synthesis and NMR Study of Some Important Glucopyranosyl Derivatives, Journal of Kerbala University, 2011, 9,42-48.
- Wolff,L., Justus Liebigs, Methode zum Ersatz des Sauerstoffatoms der Ketone und Aldehyde durch Wasserstoff, Ann. Chem.,1912,394, 59−68.
- Barakat, A., Al-Majid, A.M., Soliman, S.M., Islam, M.S., Ghawas, H.M., Yousuf, S., Choudhary, M.I., Wadood, A., Molecular structure and spectroscopic investigations combined with hypoglycemic/anticancer and docking studies of a new barbituric acid derivative, Journal of Molecular Structure, 2017,1141,624-633.
- Mayur, B., Sancheti, S., Shruti, S., Sung Yum, Antioxidant and α-glucosidase inhibitory properties of Carpesium abrotanoides, J. Med. Plant Res., 2010,4,1547–1553.
- Abbass, A.F., Zimam, E.H., Synthesis, characterization and study biological activity of some new pyrimidine and 1, 2, 3, 4-tetrazole derivatives based on sulfadiazine, International Journal of ChemTech Research,2016,9, 206-217.
Abstract Views: 243
PDF Views: 0