Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors.
Thiosemicarbazones
/ chemistry
Structure-Activity Relationship
Molecular Docking Simulation
Cholinesterase Inhibitors
/ chemistry
Carbonic Anhydrase Inhibitors
/ pharmacology
Acetylcholinesterase
/ metabolism
Spectroscopy, Fourier Transform Infrared
Carbonic Anhydrase I
Enzyme Inhibitors
/ chemistry
Molecular Structure
Isothiocyanates
DFT
enzyme inhibition
molecular docking
structure characterization
thiosemicarbazones
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Nov 2023
Nov 2023
Historique:
received:
20
07
2023
accepted:
28
09
2023
medline:
29
11
2023
pubmed:
29
9
2023
entrez:
28
9
2023
Statut:
ppublish
Résumé
Eleven new thiosemicarbazone derivatives (1-11) were designed from nine different biologically and pharmacologically important isothiocyanate derivatives containing functional groups such as fluorine, chlorine, methoxy, methyl, and nitro at various positions of the phenyl ring, in addition to the benzyl unit in the molecular skeletal structure. First, their substituted-thiosemicarbazide derivatives were synthesized from the treatment of isothiocyanate with hydrazine to synthesize the designed compounds. Through a one-step easy synthesis and an eco-friendly process, the designed compounds were synthesized with yields of up to 95 % from the treatment of the thiosemicarbazides with aldehyde derivatives having methoxy and hydroxy groups. The structures of the synthesized molecules were elucidated with elemental analysis and FT-IR,
Identifiants
pubmed: 37769192
doi: 10.1002/cbdv.202301063
doi:
Substances chimiques
Thiosemicarbazones
0
Cholinesterase Inhibitors
0
Carbonic Anhydrase Inhibitors
0
Acetylcholinesterase
EC 3.1.1.7
Carbonic Anhydrase I
EC 4.2.1.-
Enzyme Inhibitors
0
Isothiocyanates
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301063Subventions
Organisme : Anadolu University
ID : 2102 S003
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
A. Cinarli, D. Gürbüz, A. Tavman, A. S. Birteksöz, Bull. Chem. Soc. Ethiop. 2011, 25, 407-417.
S. Pandeya, D. Sriram, G. Nath, E. De Clercq, Pharm. Acta Helv. 1999, 74, 11-17.
H. Yakan, Ü. M. Koçyiğit, H. Muğlu, M. Ergul, S. Erkan, E. Güzel, P. Taslimi, İ. Gülçin, J. Biochem. Mol. Toxicol. 2022, 36, e23018.
S. Alyar, T. Şen, Ü. Ö. Özmen, H. Alyar, Ş. Adem, C. Şen, J. Mol. Struct. 2019, 1185, 416-424.
M. Verma, S. N. Pandeya, K. N. Singh, J. P. Stables, Acta Pharmaceutica 2004, 54, 49-56.
T. Aboul-Fadl, F. A. S. Bin-Jubair, O. Aboul-Wafa, European J. Medicinal Chemistry 2010, 45, 4578-4586.
S. Shukla, R. S. Srivastava, S. K. Shrivastava, A. Sodhi, P. Kumar, Med. Chem. Res. 2013, 22, 1604-1617.
S. S. Ali, E.-R. Kenawy, F. I. Sonbol, J. Sun, M. Al-Etewy, A. Ali, L. Huizi, N. A. El-Zawawy, Pharm. Res. 2018, 36, 5.
H. Muğlu, H. Yakan, A. G. A. Misbah, M. S. Çavuş, T. K. Bakır, Res. Chem. Intermed. 2021, 47, 4985-5005;
H. Muğlu, H. Yakan, T. K. Bakir, Turk. J. Chem. 2020, 44, 237-248.
S. Chigurupati, J. Med. Bioeng. 2015, 4, 363-366.
V. Mishra, S. N. Pandeya, E. DeClercq, C. Pannecouque, M. Witvrouw, Pharm. Acta Helv. 1998, 73, 215-218.
M. Tahriri, M. Yousefi, K. Mehrani, M. Tabatabaee, M. D. Ashkezari, Pharm. Chem. J. 2017, 51, 425-428.
A. Karaküçük-İyidoğan, D. Taşdemir, E. E. Oruç-Emre, J. Balzarini, European J. Medicinal Chemistry 2011, 46, 5616-5624.
B. N. Brousse, R. Massa, A. G. Moglioni, M. Martins Alho, G. Gutkind, G. Y. Moltrasio, J. the Chilean Chemical Society 2004, 49, 45-49.
N. Karali, A. Gürsoy, Farmaco (Societa chimica italiana: 1989) 1994, 49, 819-822.
U. Kulandaivelu, V. G. Padmini, K. Suneetha, B. Shireesha, J. V. Vidyasagar, T. R. Rao, J. K N, A. Basu, V. Jayaprakash, Arch. Pharm. 2011, 344, 84-90.
H. Pervez, N. Manzoor, M. Yaqub, A. Khan, K. M. Khan, F.-u.-H. Nasim, M. I. Choudhary, Lett. Drug Des. Discovery 2010, 7, 102-108.
N. P. Prajapati, K. D. Patel, R. H. Vekariya, H. D. Patel, D. P. Rajani, J. Mol. Struct. 2019, 1179, 401-410.
Z. Bakherad, M. Safavi, A. Fassihi, H. Sadeghi-Aliabadi, M. Bakherad, H. Rastegar, M. Saeedi, J. B. Ghasemi, L. Saghaie, M. Mahdavi, Chem. Biodiversity 2019, 16, e1800470.
H. Yakan, Turk. J. Chem. 2020, 44, 1085-1099.
A. R. Božić, N. Filipović, I. Novaković, S. Bjelogrlić, J. B. Nikolić, S. Z. Drmanić, A. D. Marinković, J. the Serbian Chemical Society 2017, 82, 495-508.
K. H. D. Reddy, S.-M. Lee, K. Seshaiah, R. K. Babu, J. the Serbian Chemical Society 2013, 78, 229-240.
M. Yiğit, Y. Demir, D. Barut Celepci, T. Taskin-Tok, A. Arınç, B. Yiğit, M. Aygün, İ. Özdemir, İ. Gülçin, Arch. Pharm. 2022, 355, 2200348;
S. Bilginer, S. K. Bardaweel, Y. Demir, I. Gulcin, C. Kazaz, Med. Chem. Res. 2022, 31, 925-935.
M. Hamide, Y. Gök, Y. Demir, G. Yakalı, T. T. Tok, A. Aktaş, R. Sevinçek, B. Güzel, İ. Gülçin, J. Mol. Struct. 2022, 1265, 133266;
M. S. Özaslan, R. Sağlamtaş, Y. Demir, Y. Genç, İ. Saraçoğlu, İ. Gülçin, Chem. Biodiversity 2022, 19, e202200280.
N. Oztaskin, S. Goksu, Y. Demir, A. Maras, İ. Gulcin, Molecules 2022, 27, 7426.
M. Hamide, Y. Gök, Y. Demir, R. Sevinçek, T. Taskin-Tok, B. Tezcan, A. Aktaş, İ. Gülçin, M. Aygün, B. Güzel, Chem. Biodiversity 2022, 19, e202200257.
I. Mahmudov, Y. Demir, Y. Sert, Y. Abdullayev, A. Sujayev, S. H. Alwasel, I. Gulcin, Arabian J. Chemistry 2022, 15, 103645.
I. Kraicheva, I. Tsacheva, R. Nikolova, M. Topashka-Ancheva, I. Stoineva, B. Shivachev, Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 403-409.
S. Tellamekala, M. Gundluru, S. Sarva, M. R. Nadiveedhi, M. Sudileti, R. Allagadda, A. R. Chippada, S. R. Cirandur, Synth. Commun. 2019, 49, 563-575.
Ö. Demirci, B. Tezcan, Y. Demir, T. Taskin-Tok, Y. Gök, A. Aktaş, B. Güzel, İ. Gülçin, Molecular Diversity 2022.
Y. Demir, C. Türkeş, M. S. Çavuş, M. Erdoğan, H. Muğlu, H. Yakan, Ş. Beydemir, Arch. Pharm. 2023, 356, 2200554.
H. Yakan, H. Muğlu, C. Türkeş, Y. Demir, M. Erdoğan, M. S. Çavuş, Ş. Beydemir, J. Mol. Struct. 2023, 1280, 135077.
R. J. Obaid, E. U. Mughal, N. Naeem, M. M. Al-Rooqi, A. Sadiq, R. S. Jassas, Z. Moussa, S. A. Ahmed, Process Biochem. 2022, 120, 250-259.
M. Ishaq, P. Taslimi, Z. Shafiq, S. Khan, R. Ekhteiari Salmas, M. M. Zangeneh, A. Saeed, A. Zangeneh, N. Sadeghian, A. Asari, H. Mohamad, Bioorg. Chem. 2020, 100, 103924.
M. Elkolli, N. Chafai, S. Chafaa, I. Kadi, C. Bensouici, A. Hellal, J. Mol. Struct. 2022, 1268, 133701;
N. Dawar, J. Devi, B. Kumar, A. Dubey, Inorg. Chem. Commun. 2023, 151, 110567;
R. Arshad, M. A. Khan, S. Mutahir, S. Hussain, G. H. Al-Hazmi, M. S. Refat, Polycyclic Aromat. Compd. 2023, 43, 6750-6765;
N. Mani, D. Nicksonsebastin, M. Prasath, Chemical Physics Impact 2023, 7, 100292;
K. Saranya, S. Murugavel, J. Mol. Struct. 2021, 1229, 129487;
H. Tlidjane, N. Chafai, S. Chafaa, C. Bensouici, K. Benbouguerra, J. Mol. Struct. 2022, 1250, 131853.
P. Tarasconi, S. Capacchi, G. Pelosi, M. Cornia, R. Albertini, A. Bonati, P. P. Dall′Aglio, P. Lunghi, S. Pinelli, Bioorg. Med. Chem. 2000, 8, 157-162;
M. Khalid, R. Jawaria, M. U. Khan, A. A. C. Braga, Z. Shafiq, M. Imran, H. M. A. Zafar, A. Irfan, ACS Omega 2021, 6, 16058-16065;
W. A. Arafa, M. G. Badry, J. Chemical Research 2016, 40, 385-392.
T. Lu, F. Chen, J. Computational Chemistry 2012, 33, 580-592.
S. Hashmi, S. Khan, Z. Shafiq, P. Taslimi, M. Ishaq, N. Sadeghian, H. S. Karaman, N. Akhtar, M. Islam, A. Asari, H. Mohamad, İ. Gulçin, Bioorg. Chem. 2021, 107, 104554.
P. Eraslan-Elma, A. Akdemir, E. Berrino, M. Bozdağ, C. T. Supuran, N. Karalı, Arch. Pharm. 2022, 355, 2200023.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997, 23, 3-25.
E. M. Duffy, W. L. Jorgensen, J. the American Chemical Society 2000, 122, 2878-2888.
A. Benmohammed, O. Khoumeri, A. Djafri, T. Terme, P. Vanelle, Molecules 2014, 19, 3068-3083.
G. L. Ellman, K. D. Courtney, V. Andres Jr, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88-95.
M. Kalaycı, C. Türkeş, M. Arslan, Y. Demir, Ş. Beydemir, Arch. Pharm. 2021, 354, 2000282.
J. A. Verpoorte, S. Mehta, J. T. Edsall, J. Biol. Chem. 1967, 242, 4221-4229.
Ü. Yaşar, İ. Gönül, C. Türkeş, Y. Demir, Ş. Beydemir, ChemistrySelect 2021, 29, 7278-7284.
C. Türkeş, M. Arslan, Y. Demir, L. Cocaj, A. R. Nixha, Ş. Beydemir, Bioorg. Chem. 2019, 89, 103004.
H. Lineweaver, D. Burk, J. the American Chemical Society 1934, 56, 658-666.
B. Sever, C. Türkeş, M. D. Altıntop, Y. Demir, G. A. Çiftçi, Ş. Beydemir, Arch. Pharm. 2021, 354, 2100294;
S. Askin, H. Tahtaci, C. Türkeş, Y. Demir, A. Ece, G. A. Çiftçi, Ş. Beydemir, Bioorg. Chem. 2021, 113, 105009;
Y. Demir, H. Ceylan, C. Türkeş, Ş. Beydemir, J. Biomol. Struct. Dyn. 2022, 40, 12008-12021;
G. Yapar, H. Esra Duran, N. Lolak, S. Akocak, C. Türkeş, M. Durgun, M. Işık, Ş. Beydemir, Bioorg. Chem. 2021, 117, 105473;
C. Türkeş, Y. Demir, Ş. Beydemir, ChemistrySelect 2021, 6, 11915-11924;
C. Türkeş, A. Ö. Kesebir, Y. Demir, Ö. İ. Küfrevioğlu, Ş. Beydemir, ChemistrySelect 2021, 6, 11137-11143;
B. Çalışkan, Y. Demir, C. Türkeş, Biotechnol. Appl. Biochem. 2022, 69, 2273-2283.
C. Türkeş, Y. Demir, Ş. Beydemir, J. Biomol. Struct. Dyn. 2021, 39, 1672-1680;
B. Sever, C. Türkeş, M. D. Altıntop, Y. Demir, Ş. Beydemir, International J. Biological Macromolecules 2020, 163, 1970-1988.
M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. Petersson, See also: URL: http://www.gaussian.Com2009.
P. Hohenberg, W. Kohn, B864 1964;
W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A1133.
R. F. W. Bader, Acc. Chem. Res. 1985, 18, 9-15;
R. F. W. Bader, Chem. Rev. 1991, 91, 893-928.
T. Lu, Q. Chen, Chemistry-Methods 2021, 1, 231-239.
S. Chakravarty, K. K. Kannan, J. Mol. Biol. 1994, 243, 298-309.
K. H. Sippel, A. H. Robbins, J. Domsic, C. Genis, M. Agbandje-McKenna, R. McKenna, Acta Crystallogr. Sect. F 2009, 65, 992-995.
K. V. Dileep, K. Ihara, C. Mishima-Tsumagari, M. Kukimoto-Niino, M. Yonemochi, K. Hanada, M. Shirouzu, K. Y. J. Zhang, Int. J. Biol. Macromol. 2022, 210, 172-181.
Schrödinger Release 2023-1: Protein Preparation Wizard, Schrödinger, LLC, New York, NY, 2023;
A. Buza, C. Türkeş, M. Arslan, Y. Demir, B. Dincer, A. R. Nixha, Ş. Beydemir, Int. J. Biol. Macromol. 2023, 239, 124232.
Schrödinger Release 2023-1: LigPrep, Schrödinger, LLC, New York, NY, 2023;
D. Osmaniye, C. Türkeş, Y. Demir, Y. Özkay, Ş. Beydemir, Z. A. Kaplancıklı, Archiv der Pharmazie 2022, 355, 2200132.
Schrödinger Release 2023-1: Epik, Schrödinger, LLC, New York, NY, 2023;
J. C. Shelley, A. Cholleti, L. L. Frye, J. R. Greenwood, M. R. Timlin, M. Uchimaya, J. Comput.-Aided Mol. Des. 2007, 21, 681-691.
Schrödinger Release 2023-1: SiteMap, Schrödinger, LLC, New York, NY, 2023;
T. A. Halgren, J. Chem. Inf. Model. 2009, 49, 377-389.
Schrödinger Release 2023-1: Receptor Grid Generation, Schrödinger, LLC, New York, NY, 2023;
N. Lolak, S. Akocak, M. Durgun, H. E. Duran, A. Necip, C. Türkeş, M. Işık, Ş. Beydemir, Mol. Diversity 2022. 27, 1735-1749.
Schrödinger Release 2023-1: Glide, Schrödinger, LLC, New York, NY, 2023;
S. A. Güngör, M. Köse, M. Tümer, C. Türkeş, Ş. Beydemir, J. Biomol. Struct. Dyn. 2022, 1-11;
Ö. Güleç, C. Türkeş, M. Arslan, Y. Demir, B. Dincer, A. Ece, Ş. Beydemir, J. Biomolecular Structure and Dynamics 1-19. https://doi.org/10.1080/07391102.2023.2240889
R. A. Friesner, J. L. Banks, R. B. Murphy, T. A. Halgren, J. J. Klicic, D. T. Mainz, M. P. Repasky, E. H. Knoll, M. Shelley, J. K. Perry, D. E. Shaw, P. Francis, P. S. Shenkin, J. Med. Chem. 2004, 47, 1739-1749;
T. A. Halgren, R. B. Murphy, R. A. Friesner, H. S. Beard, L. L. Frye, W. T. Pollard, J. L. Banks, J. Med. Chem. 2004, 47, 1750-1759;
K. Yararli, E. B. Ozer, S. Bayindir, C. Caglayan, C. Turkes, S. Beydemir, J. Mol. Struct. 2023, 1276, 134783.
Schrödinger Release 2023-1: Prime, Schrödinger, LLC, New York, NY, 2023;
G. Barreiro, C. R. W. Guimarães, I. Tubert-Brohman, T. M. Lyons, J. Tirado-Rives, W. L. Jorgensen, J. Chem. Inf. Model. 2007, 47, 2416-2428;
C. Kakakhan, C. Türkeş, Ö. Güleç, Y. Demir, M. Arslan, G. Özkemahlı, Ş. Beydemir, Bioorg. Med. Chem. 2023, 77, 117111.
Schrödinger Release 2023-1: QikProp, Schrödinger, LLC, New York, NY, 2023;
L. Ioakimidis, L. Thoukydidis, A. Mirza, S. Naeem, J. Reynisson, QSAR Comb. Sci. 2008, 27, 445-456;
Ö. Güleç, C. Türkeş, M. Arslan, Y. Demir, Y. Yeni, A. Hacımüftüoğlu, E. Ereminsoy, Ö. İ. Küfrevioğlu, Ş. Beydemir, Mol. Diversity 2022, 26, 2825-2845.