Synthesis, molecular docking, and biological activities of new cyanopyridine derivatives containing phenylurea.
Acetylcholinesterase
/ metabolism
Butyrylcholinesterase
/ metabolism
Cholinesterase Inhibitors
/ chemical synthesis
Dose-Response Relationship, Drug
Glycoside Hydrolase Inhibitors
/ chemical synthesis
Glycoside Hydrolases
/ antagonists & inhibitors
Humans
Molecular Docking Simulation
Molecular Structure
Phenylurea Compounds
/ chemistry
Pyridines
/ chemical synthesis
Structure-Activity Relationship
acetylcholinesterase
carbonic anhydrase
chalcone
cyanopyridine
molecular docking
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
Apr 2021
Apr 2021
Historique:
revised:
07
11
2020
received:
04
09
2020
accepted:
13
11
2020
pubmed:
11
12
2020
medline:
21
10
2021
entrez:
10
12
2020
Statut:
ppublish
Résumé
A new class of cyanopyridine derivatives (10a-e and 11a-e) containing the phenylurea unit was synthesized and tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase (α-Gly). The new cyanopyridine derivatives showed K
Identifiants
pubmed: 33300644
doi: 10.1002/ardp.202000334
doi:
Substances chimiques
Cholinesterase Inhibitors
0
Glycoside Hydrolase Inhibitors
0
Phenylurea Compounds
0
Pyridines
0
Acetylcholinesterase
EC 3.1.1.7
Butyrylcholinesterase
EC 3.1.1.8
Glycoside Hydrolases
EC 3.2.1.-
3-cyanopyridine
X64V0K6260
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000334Subventions
Organisme : Sivas Cumhuriyet University
ID : RGD-020
Informations de copyright
© 2020 Deutsche Pharmazeutische Gesellschaft.
Références
V. Polshettiwar, R. S. Varma, Pure Appl. Chem. 2008, 80, 777.
A. S. Girgis, A. Kalmouch, H. M. Hosni, Amino Acids 2004, 26, 139.
S. F. Mohamed, M. M. Youssef, A.E.l-G.E. Amr, E. R. Kotb, Sci. Pharm. 2008, 76, 279.
J. L. Sebat, A. J. Paszczynskı, M. S. Cortese, R. L. Crawford, Appl. Environ. Microbiol. 2001, 67, 3934.
N. A. Abdel-Latif, N. M. Sabry, A. M. Mohamed, M. M. Abdulla, Monatsh. Chem. 2007, 138, 715.
A. S. Girgis, N. Mishriky, M. Ellithey, H. M. Hosnia, H. Farag, Bioorg. Med. Chem. 2007, 15, 2403.
P. L. Ferrarinia, C. Mori, M. Badawneh, V. Calderone, R. Greco, C. Manera, A. Martinelli, P. Nieri, G. Saccomanni, J. Med. Chem. 2000, 35, 815.
G. Puerstinger, J. Paeshuyse, S. Heinrich, J. Mohr, N. Schraffl, E. De Clercqb, J. Neyts, Bioorg. Med. Chem. Lett. 2007, 17, 5111.
A.-G. E. Amr, A. M. Mohamed, S. F. Mohamed, N. A. Abdel-Hafez, A. E.-F. G. Hammam, Bioorg. Med. Chem. 2006, 14, 5481.
S.-J. Su, H. Sasabe, T. Takeda, J. Kido, Chem. Mater. 2008, 20, 1691.
P. N. W. Baxter, Chem. - Eur. J. 2002, 8, 5250.
G. Deepa, R. Balamurugan, P. Kannan, J. Mol. Struct. 2010, 963, 219.
V. Raghukumar, D. Thirumalai, V. T. Ramakrishnan, V. Karunakarac, P. Ramamurthy, Tetrahedron 2003, 59, 3761.
A. Galstyan, P. J. S. Miguel, B. Lippert, Inorg. Chim. Acta 2011, 374, 453.
Y. Gülkok, T. Bi̇çer, F. K. Onurdağ, S. Özgen, Turk. J. Chem. 2012, 36, 279.
D. K. Ramesh, S. P. Gangadhar, S. A. Katti, Int. J. Res. Pharm. Chem. 2013, 3, 2231.
P. Umadevi, K. Deepti, I. Srinath, G. Vijayalakshmi, M. Tarakaramji, Int. J. Pharm. Pharm. Sci. 2012, 4, 379.
S. Cherala, H. Lingabathula, R. Ganta, S. Ampati, S. Manda, E-J. Chem. 2012, 9, 2510.
H. J. Cho, M. I. El-Gamal, C.-H. Oh, S. H. Lee, G. Kim, J. H. Hong, H. S. Choi, K. H. Yoo, Bull. Korean Chem. Soc. 2012, 33, 3635.
C.-S. Lu, K. Tang, Y. Li, B. Jin, D.-L. Yin, C. Ma, X.-G. Chen, H.-H. Huang, Yao Xue Xue Bao 2013, 48, 709.
A. Biçer, R. Kaya, G. Yakali, M. S. Gültekin, G. Turgut Cin, İ. Gülçin, J. Mol. Struct. 2020, 1204, 127453.
S. Bilginer, B. Gonder, H. İ. Gul, R. Kaya, İ. Gulcin, B. Anil, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2020, 35, 325.
N. Sepehri, M. Mohammadi-Khanaposhtani, N. Asemanipoor, S. Hosseini, M. Biglar, B. Larijani, M. Mahdavi, H. Hamedifar, P. Taslimi, N. Sadeghian, I. Gulcin, Arch. Pharm. (Weinheim) 2020, 353, e2000109.
P. Taslimi, F. Turkan, A. Cetin, H. Burhan, M. Karaman, İ. Bildirici, İ. Gülçin, F. Şen, Bioorg. Chem. 2019, 92, 103213.
A. T. Bilgiçli, H. G. Bilgiçli, A. Günsel, H. Pişkin, B. Tüzün, M. N. Yarasir, M. Zengin, J. Photochem. Photobiol., A 2020, 389, 112287.
H. G. Bilgiçli, A. T. Bilgiçli, A. Günsel, B. Tüzün, D. Ergön, M. N. Yarasir, M. Zengin, Appl. Organomet. Chem. 2020, 34, e5624.
A. Günsel, A. T. Bilgiçli, B. Tüzün, H. Pişkin, M. N. Yarasir, B. Gündüz, New J. Chem. 2020, 44, 369.
A. Günsel, A. T. Bilgiçli, H. Pişkin, B. Tüzün, M. N. Yarasir, B. Gündüz, Dalton Trans. 2019, 48, 14839.
J. Cheung, E. N. Gary, K. Shiomi, T. L. Rosenberry, ACS Med. Chem. Lett. 2013, 4, 1091.
U. Kosak, B. Brus, D. Knez, S. Zakelj, J. Trontelj, A. Pislar, R. Sink, M. Jukic, M. Zivin, A. Podkowa, F. Nachon, X. Brazzolotto, J. Stojan, J. Kos, N. Coquelle, K. Salat, J.-P. Colletier, S. Gobec, J. Med. Chem. 2018, 61, 119.
A. M. Golubev, R. A. P. Nagem, J. R. Brandao Neto, K. N. Neustroev, E. V. Eneyskaya, A. A. Kulminskaya, K. A. Shabalin, A. N. Savel'ev, I. Polikarpov, J. Mol. Biol. 2004, 339, 413, 2004.
D. Kısa, N. Korkmaz, P. Taslimi, B. Tuzun, Ş. Tekin, A. Karadag, F. Şen, Bioorg. Chem. 2020, 101, 104066.
F. Sonmez, S. Sevmezler, A. Atahan, M. Ceylan, D. Demir, N. Gencer, O. Arslan, M. Kucukislamoglu, Bioorg. Med. Chem. Lett. 2011, 21, 7479.
A. Atahan, N. Gencer, C. Bilen, E. Yavuz, H. Genc, F. Sonmez, M. Zengin, M. Ceylan, M. Kucukislamoglu, ChemistrySelect 2018, 3, 529.
N. Gençer, Ç. Bilen, D. Demir, A. Atahan, M. Ceylan, M. Küçükislamoğlu, Artif. Cells, Nanomed., Biotechnol. 2013, 41, 384.
J. N. Dominguez, C. Leon, J. Rodrigues, N. G. de Dominguez, J. Gut, P. J. Rosenthal, J. Med. Chem. 2005, 48, 3654.
H. Gezegen, C. Hepokur, U. Tutar, M. Ceylan, Chem. Biodivers. 2017, 14, e1700223.
G. L. Ellman, K. D. Courtney, V. Andres Jr., R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88.
S. Ökten, M. Ekiz, A. Tutar, B. Bütün, U. M. Koçyiğit, G. Topçu, İ. Gulcin, Ind. J. Pharm. Educ. Res. 2019, 53, 268.
Y. Tao, Y. F. Zhang, Y. Y. Cheng, Y. Wang, Biomed. Chromatogr. 2013, 27, 148.
B. Tüzün, E. Saripinar, J. Iran Chem. Soc. 2020, 17, 985.
B. Tüzün, Spectrochim. Acta, Part A 2020, 227, 117663.
K. Sayin, A. Üngördü, Spectrochim. Acta, Part A 2019, 220, 117102.
K. Sayin, D. Karakaş, Spectrochim. Acta, Part A 2018, 202, 276.
K. Sayin, D. Karakaş, J. Mol. Struct. 2018, 1158, 57.
K. Sayin, A. Üngördü, Spectrochim. Acta, Part A 2018, 193, 147.
K. Sayin, D. Karakaş, J. Mol. Struct. 2017, 1146, 191.
R. Jayarajan, R. Satheeshkumar, T. Kottha, S. Subbaramanian, K. Sayin, G. Vasuki, Spectrochim. Acta, Part A 2020, 229, 117861.
A. Üngördü, K. Sayin, Chem. Phys. Lett. 2019, 733, 136677.
H. U. Celebioglu, Y. Erden, F. Hamurcu, P. Taslimi, O. S. Şentürk, Ü. Ö. Özmen, B. Tuzun, İ. Gulçin, J. Biomol. Struct. Dyn. 2020. https://doi.org/10.1080/07391102.2020.1792345
F. Türkan, P. Taslimi, S. M. Abdalrazaq, A. Aras, Y. Erden, H. U. Celebioglu, B. Tuzun, M. S. Ağırtaş, İ. Gülçin, J. Biomol. Struct. Dyn. 2020. https://doi.org/10.1080/07391102.2020.1768901
P. Taslimi, Y. Erden, S. Mamedov, L. Zeynalova, N. Ladokhina, R. Tas, B. Tuzun, A. Sujayev, N. Sadeghian, S. H. Alwasel, I. Gulcin, J. Biomol. Struct. Dyn. 2020. https://doi.org/10.1080/07391102.2020.1763838
C. A. Lipinski, Drug Discov. Today: Technol. 2004, 1, 337.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 1997, 23, 3.
W. J. Jorgensen, E. M. Duffy, Adv. Drug Deliv. Rev. 2002, 54, 355.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision D.01, Gaussian Inc., Wallingford, CT 2009.
L. Schrodinger, Small-Molecule Drug Discovery Suite 2019-4 2019.
(a) Schrödinger Release 2019-4: Protein Preparation Wizard; (b) Epik, Schrödinger, LLC, New York, NY 2016; (c) Impact, Schrödinger, LLC, New York, NY 2016; (d) Prime, Schrödinger, LLC, New York, NY 2019.
R. A. Friesner, R. B. Murphy, M. P. Repasky, L. L. Frye, J. R. Greenwood, T. A. Halgren, P. C. Sanschagrin, D. T. Mainz, J. Med. Chem. 2006, 49, 6177.
G. M. Sastry, M. Adzhigirey, T. Day, R. Annabhimoju, W. Sherman, J. Comput.-Aided Mol. Des. 2013, 27, 221.
Schrödinger Release 2019-4: LigPrep, Schrödinger, LLC, New York, NY 2019.
Q. Du, Y. Qian, X. Yao, W. Xue, J. Biomol. Struct. Dyn. 2020, 38, 625.
Schrödinger Release 2020-1: QikProp, Schrödinger, LLC, New York, NY 2020.