Synthesis and docking study of benzimidazole-triazolothiadiazine hybrids as aromatase inhibitors.
A549 Cells
Animals
Antineoplastic Agents
/ chemical synthesis
Aromatase
Aromatase Inhibitors
/ chemical synthesis
Benzimidazoles
/ chemistry
Cell Proliferation
/ drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
MCF-7 Cells
Mice
Molecular Docking Simulation
Molecular Structure
NIH 3T3 Cells
Structure-Activity Relationship
Thiadiazines
/ chemistry
MCF-7
aromatase
benzimidazole
molecular docking
triazolothiadiazine
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
May 2020
May 2020
Historique:
received:
09
01
2020
revised:
18
02
2020
accepted:
19
02
2020
pubmed:
12
3
2020
medline:
31
12
2020
entrez:
12
3
2020
Statut:
ppublish
Résumé
Aromatase is involved in the biosynthesis of estrogen and thus is a critical target for breast cancer. In this study, to identify new aromatase enzyme inhibitors, seven 3-[4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenyl]-6-(substituted phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives were synthesized. First, a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay was performed to determine the inhibitory activity of the synthesized compounds on the MCF-7 cell line. The aromatase inhibitory activity was determined for the active compounds 5b, 5c, 5e, and 5g on the MCF-7 cell line. Compound 5g showed significant aromatase inhibitory activity (IC
Identifiants
pubmed: 32159244
doi: 10.1002/ardp.202000008
doi:
Substances chimiques
Antineoplastic Agents
0
Aromatase Inhibitors
0
Benzimidazoles
0
Thiadiazines
0
Aromatase
EC 1.14.14.1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000008Informations de copyright
© 2020 Deutsche Pharmazeutische Gesellschaft.
Références
C. Chamduang, R. Pingaew, V. Prachayasittikul, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Bioorg. Chem. 2019, 93, 103327.
Y. Geng, Y. Liu, K. Lu, L. Zhang, X. Zhang, Y. Dai, In IOP Conf. Series: Earth and Environmental Science 2018, 199, 032062.
N. Sinthupoom, V. Prachayasittikul, R. Pingaew, A. Worachartcheewan, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Lett. Drug Des. Discov. 2017, 14, 880.
R. W. Brueggemeier, J. C. Hackett, E. S. Diaz-Cruz, Endocr. Rev. 2005, 26, 331.
R. Leechaisit, R. Pingaew, V. Prachayasittikul, A. Worachartcheewan, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Bioorg. Med. Chem. 2019, 27, 115040.
M. Fantacuzzi, B. De Filippis, M. Gallorini, A. Ammazzalorso, L. Giampietro, C. Maccallini, A. Cataldi, Eur. J. Med. Chem. 2019, 185, 111815.
S. Ozcan-Sezer, E. Ince, A. Akdemir, Ö. Ö. Ceylan, S. Suzen, H. Gurer-Orhan, Xenobiotica 2019, 49, 549.
R. Pingaew, V. Prachayasittikul, N. Anuwongcharoen, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Bioorg. Chem. 2018, 79, 171.
M. M. Ghorab, M. S. Alsaid, N. Samir, G. A. Abdel-Latif, A. M. Soliman, F. A. Ragab, D. A. A. El Ella, Eur. J. Med. Chem. 2017, 134, 304.
W. Shoombuatong, N. Schaduangrat, C. Nantasenamat, EXCLI J. 2018, 17, 688.
D. Ghosh, J. Lo, C. Egbuta, J. Med. Chem. 2016, 59, 5131.
A. M. Prior, X. Yu, E. J. Park, T. P. Kondratyuk, Y. Lin, J. M. Pezzuto, D. Sun, Bioorg. Med. Chem. Lett. 2017, 27, 5393.
C. Amaral, M. R. T. Toloi, L. D. Vasconcelos, M. J. V. Fonseca, G. Correia-da-Silva, N. Teixeira, Food Funct. 2017, 8, 3064.
C. Amaral, C. L. Varela, J. Maurício, A. F. Sobral, S. C. Costa, F. M. Roleira, N. Teixeira, J. Steroid Biochem. Mol. Biol. 2017, 171, 218.
A. S. Bhatnagar, A. Hausler, K. Schieweck, M. Lang, R. Bowman, J. Steroid Biochem. Mol. Biol. 1990, 37, 1021.
P. M. Sable, L. C. Potey, Pharm. Chem. J. 2018, 52, 438.
G. Gilardi, G. Di Nardo, Rend. Lincei 2017, 28, 159.
V. Prachayasittikul, R. Pingaew, A. Worachartcheewan, S. Sitthimonchai, C. Nantasenamat, S. Prachayasittikul, V. Prachayasittikul, EXCLI J. 2017, 16, 714.
P. Asadi, G. Khodarahmi, H. Farrokhpour, F. Hassanzadeh, L. Saghaei, Res. Pharm. Sci. 2017, 12, 233.
A. Mojaddami, A. Sakhteman, M. Fereidoonnezhad, Z. Faghih, A. Najdian, S. Khabnadideh, Z. Rezaei, Res. Pharm. Sci. 2017, 12, 21.
Z. Song, Y. Liu, Z. Dai, W. Liu, K. Zhao, T. Zhang, Y. Dai, Bioorg. Med. Chem. 2016, 24, 4723.
N. Adhikari, S. A. Amin, T. Jha, S. Gayen, Can. J. Chem. 2017, 95, 1285.
H. Karaca Gençer, U. Acar Çevik, S. Levent, B. N. Sağlık, B. Korkut, Y. Özkay, S. Ilgın, Y. Öztürk, Molecules 2017, 22, 507.
A. E. Evren, L. Yurttas, B. Ekselli, G. Akalin-Ciftci, Phosphorus, Sulfur Silicon Relat. Elem. 2019, 194, 820. https://doi.org/
A. E. Evren, L. Yurttaş, B. Eksellı, G. Akalın-Cıftcı, Lett. Drug. Des. Discov. 2019, 16, 547.
D. Ghosh, J. Griswold, M. Erman, W. Pangborn, Nature 2009, 457, 219.
Maestro, version 10.6, Schrödinger LLC, New York, NY 2016.
Schrödinger Suite 2016 Update 2, Schrödinger LLC, New York, NY 2016.
LigPrep, version 3.8, Schrödinger LLC, New York, NY 2016.
Glide, version 7.1, Schrödinger LLC, New York, NY 2016.