Design, in Silico Studies and Biological Evaluation of New Chiral Thiourea and 1,3-Thiazolidine-4,5-dione Derivatives.
1,3-thiazolidine-4,5-dione
biological activity
chiral, thiourea
molecular docking
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Aug 2023
Aug 2023
Historique:
received:
02
05
2023
accepted:
20
07
2023
medline:
24
8
2023
pubmed:
21
7
2023
entrez:
21
7
2023
Statut:
ppublish
Résumé
In this study, new chiral thiourea and 1,3-thiazolidine-4,5-dione derivatives were synthesized, it was aimed to evaluate the various biological activities and molecular docking of these compounds. Firstly, the new thioureas (1-16) were obtained by reacting 1-naphthylisothiocyanate with different chiral amines. Then, the chiral thioureas were cyclized with oxalyl chloride to obtain 1,3-thiazolidine-4,5-dione derivatives (17-32). All compounds were evaluated with several in vitro antioxidant and enzyme inhibition activities. Compound 30 was the most active compound against AChE, with a value of IC
Identifiants
pubmed: 37477542
doi: 10.1002/cbdv.202300626
doi:
Substances chimiques
Thiazolidines
0
Thiourea
GYV9AM2QAG
Antioxidants
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300626Subventions
Organisme : Gaziantep University Scientific Research Projects Governing Unit
ID : FEF.YLT.20.18
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
J. L. Price, P. B. Davis, J. C. Morris, D. L. White, Neurobiol. Aging 1991, 12(4), 295-312.
L. Frölich, J. Neural Transm. 2002, 109(7-8), 1003-1013.
D. R. Liston, J A. Nielsen, A. Villalobos, D. Chapin, S. B. Jones, S. T. Hubbard, I. A. Shalaby, A. Ramirez, D. Nason, W. F. White, Eur. J. Pharm. 2004, 486(1), 9-17.
C. Chianella, D. Gragnaniello, P. MaisanoDelser, M. F. Visentini, E. Sette, M. R. Tola, G. Barbujani, S. Fuselli, Eur. Clin. Pharmacol. 2011, 67(11), 1147-1157.
J. Birks, Cochrane Database Syst. Rev. 2006, 1, 2-3.
A. Corbett, J. Smith, C. Ballard, Expert Rev. Neurother. 2012, 12(5), 535-543.
U. Rashid, F. L. Ansari, in Drug Design and Discovery in Alzheimer's Disease, 1st ed. (Eds.: A. Rahman, M. I. Choudhary), Bentham Science Publishers, 2014, pp 40-141.
M. L. Bolognesi, M. Rosini, V. Andrisano, M. Bartolini, A. Minarini, V. Tumiatti, C. Melchiorre, Curr. Pharm. Des. 2009, 15(6), 601-613.
M. Yiğit, D. B. Celepci, P. Taslimi, B. Yiğit, E. Çetinkaya, İ. Özdemir, M. Aygün, İ. Gülçin, Bioorg. Chem. 2021, 120, 105566.
T. Hasegawa, Inter. J. Mol. Sci. 2010, 11(3), 1082-1089.
D. L. Weeks, S. Eskandari, D. R. Scott, G. A Sachs, Science 2000, 287(5452), 482-485.
R. Ge, X. Sun, Med. Hypotheses 2011, 77, 788-790.
G. Albaret, E. Sifré, P. Floch, S. Laye, A. Aubert, P. Dubus, L. Azzi-Martin, A. Giese, N. Salles, F. Mègraud, C. Varon, P. Lehours, C. Roubaud-Baudron, J. Alzheimer′s Dis. 2020, 73, 801-809.
R. D. Bell, B. V. Zlokovic, Acta Neuropathol. 2009, 118(1), 103-113.
J. Kountouras, M. Tsolaki, E. Gavalas, M. Boziki, C. Zavos, P. Karatzoglou, D. Chatzopoulos, I. Venizelos, Neurology 2006, 66(6), 938-940.
A. Federico, E. Cardaioli, P. Da Pozzo, P. Formichi, G. N. Gallus, E. Radi, J. Neurol. Sci. 2012, 322(1-2), 254-262.
http://www.swissadme.ch (Accessed on 23 Jan 2022).
M. Taha, N. H. Ismail, S. Imran, A. Wadood, F. Rahim, K. M. Khan, M. Riaz, Bioorg. Chem. 2016, 66, 80-87.
P. Liu, C. Shu, L. Liu, Q. Huang, Y. Peng, Bioorg. Med. Chem. 2016, 24, 1866-1887.
S. Mutahir, M. A. Khan, I. U. Khan, M. Yar, M. Ashraf, S. Tariq, R. L. Ye, B. J. Zhou, Eur. J. Med. Chem. 2017, 134, 406-414.
S. Bayındır, C. Çaglayan, M. Karaman, I. Gülçin, Bioorg. Chem. 2019, 90, 103096.
D. V. Patel, N. R. Patel, A. M. Kanhed, D. M. Teli, K. B. Patel, P. D. Joshi, S. P. Patel, P. M. Gandhi, B. N. Chaudhary, N. K. Prajapati, K. V. Patel, M. R. Yadav, Bioorg. Chem. 2020, 101, 103977.
M. Taha, F. Rahim, H. Ullah, A. Wadood, R. K. Farooq, S. A. Ali Shah, M. Nawaz, Z. A. Zakaria, Sci. Rep. 2020, 10, 10673.
W. Huang, H. Yu, R. Sheng, J. Li, Y. Hu, Bioorg. Med. Chem. 2008, 16, 10190-10197.
Arshia, F. Begum, N. B. Almandil, M. A. Lodhi, K. M. Khan, A. Hameed, S. Perveen, Bioorg. Med. Chem. 2019, 27(6), 1009-1022.
S. Song, H. Lee, Y. Jin, Y. M. Ha, S. Bae, H. Y. Chung, H. Suh, Bioorg. Med. Chem. Lett. 2007, 17(2), 461-464.
S. Karakuş, S. Rollas, II Farmaco 2002, 57(7), 577-581.
N. Karaman, R. A. Zainel, H. A. Kapkaç, H. K. Gencer, S. Ilgın, A. B. Karaduman, A. Karaküçük-İyidoğan, E. E. Oruç-Emre, B. Koçyiğit-Kaymakçıoğlu, Arch. Pharm. 2018, 351(9), 1-15.
N. Sunduru, K. Srivastava, S. Rajakumar, S. K. Puri, J. K. Saxena, P. M. S. Chauhan, Bioorg. Med. Chem. Lett. 2009, 19(9), 2570-2573.
İ. N. Yıldız, E. E. Oruç-Emre, D. Taşdemir, A. Karaküçük-İyidoğan, M. Ulaşlı, H. Bayram, J. Chin. Chem. Soc. 2017, 64(3), 321-330.
E. E. Oruç, S. Rollas, F. Kandemirli, N. Shvets, A. S. Dimoglo, J. Med. Chem. 2004, 47(27), 6760-6767.
R. D. Smith, A. L. Engdahl, J. B. Dunbar, H. A. Carlson, J. Chem. Inf. Model. 2012, 52, 2098-2106.
D. L. Mobley, K. A. Dill, Structure 2009, 17, 489-498.
D. Barak, C. Kronmang, A. Ordentlichg, N. Ariel, J. Bio. Chem. 1994, 269, 6296-6305.
D. M. Quinn, Chem. Rev. 1987, 87, 955-979.
J. E. Haux, G. B. Quistad, J. E. Casida, Chem. Res. Toxicol. 2000, 13, 646-651.
I. R. Macdonald, E. Martin, T. L. Rosenberry, S. Darvesh, Biochemistry 2012, 51, 7046-7053.
C. Zou, W. Huang, G. Zhao, X. Wan, X. Hu, Y. Jin, J. Li, J. Liu, Molecules 2017, 22(11), 1836.
A. Juszkiewicz, W. Zaborska, J. Sepioł, M. Góra, A. Zaborska, J. Enzyme Inh. Med. Chem. 2013, 18, 419-424.
I. Muegge, Med. Res. Rev. 2003, 23, 302-321.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997, 46, 3-26.
W. J. Egan, K. M. Merz, J. J. Baldwin, J. Med. Chem. 2000, 43(21), 3867-3877.
Y. Sicak, Med. Chem. Res. 2021, 30, 1557-1568.
A. Daina, V. Zoete, ChemMedChem 2016, 11, 1117-1121.
Y. Sicak, Turkish J. Chemistry 2022, 46, 665-676.
H. E. Miller, J. Am. Oil Chem. Soc. 1971, 48, 91.
M. S. Blois, Nature 1958, 181, 1199-1200.
R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Rad. Biol. Med. 1999, 26(9-10), 1231-1237.
M. Öztürk, F. Aydoğmuş-Öztürk, M. E. Duru, G. Topçu, Food Chem. 2007, 103(2), 623-630.
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7(2), 88-95.
http://www.rcsb.org/pdb (Accessed on 9 Jan 2022).
E. Jurrus, D. Engel, K. Star, K. Monson, J. Brandi, L. E. Felberg, D. H. Brookes, L. Wilson, J. Chen, K. Liles, M. Chun, P. Li, D. W. Gohara, T. Dolinsky, R. Konecny, D. R. Koes, J. E. Nielsen, T. Head-Gordon, W. Geng, R. Krasny, G. W. Wei, M. J. Holst, J. A. McCammon, N. A. Baker, Protein Sci. 2018, 27, 112-128.
BIOVIA, Dassault Systèmes, BIOVIA Workbook, Release 2020; BIOVIA Pipeline Pilot, Release 2020, San Diego: Dassault Systèmes.
P. A. Ravindranath, S. Forli, D. S. Goodsell, A. J. Olson, M. F. Sanner, PLoS Comput. Biol. 2015, 11(12), e1004586.
G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comp. Chem. 2009, 30(16), 2785-2791.