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Novel 2-[thio]acetamide linked quinazoline/1,2,4-triazole/chalcone hybrids: Design, synthesis, and anticancer activity as EGFR inhibitors and apoptotic inducers.

التفاصيل البيبلوغرافية
العنوان: Novel 2-[thio]acetamide linked quinazoline/1,2,4-triazole/chalcone hybrids: Design, synthesis, and anticancer activity as EGFR inhibitors and apoptotic inducers.
المؤلفون: Abdelkhalek AS; Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt., Kothayer H; Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt., Soltan MK; Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt.; Pharmacy Program, Oman College of Health Sciences, Muscat, Sultanate of Oman., Ibrahim SM; Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt., Elbaramawi SS; Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt.
المصدر: Archiv der Pharmazie [Arch Pharm (Weinheim)] 2024 Jul; Vol. 357 (7), pp. e2300627. Date of Electronic Publication: 2024 Apr 09.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Verlag GmbH & Co. KGaA Country of Publication: Germany NLM ID: 0330167 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-4184 (Electronic) Linking ISSN: 03656233 NLM ISO Abbreviation: Arch Pharm (Weinheim) Subsets: MEDLINE
أسماء مطبوعة: Publication: <2005->: Weinheim Germany : Wiley-VCH Verlag GmbH & Co. KGaA
Original Publication: Weinheim, Verlag Chemie GmbH.
مواضيع طبية MeSH: ErbB Receptors*/antagonists & inhibitors , ErbB Receptors*/metabolism , Antineoplastic Agents*/pharmacology , Antineoplastic Agents*/chemical synthesis , Antineoplastic Agents*/chemistry , Apoptosis*/drug effects , Quinazolines*/pharmacology , Quinazolines*/chemistry , Quinazolines*/chemical synthesis , Drug Design* , Cell Proliferation*/drug effects , Triazoles*/pharmacology , Triazoles*/chemistry , Triazoles*/chemical synthesis , Drug Screening Assays, Antitumor* , Molecular Docking Simulation* , Protein Kinase Inhibitors*/pharmacology , Protein Kinase Inhibitors*/chemical synthesis , Protein Kinase Inhibitors*/chemistry, Humans ; Structure-Activity Relationship ; Cell Line, Tumor ; Molecular Structure ; Dose-Response Relationship, Drug ; Chalcones/pharmacology ; Chalcones/chemical synthesis ; Chalcones/chemistry ; HCT116 Cells ; Acetamides/pharmacology ; Acetamides/chemistry ; Acetamides/chemical synthesis ; MCF-7 Cells ; Chalcone/pharmacology ; Chalcone/chemistry ; Chalcone/chemical synthesis
مستخلص: Novel triazoloquinazolines carrying the 2-[thio]acetamide entity (4 and 5a-d) and triazoloquinazoline/chalcone hybrids incorporating the 2-[thio]acetamide linker (8a-b and 9a-f) were developed as anticancer candidates. NCI screening of the synthesized compounds at 10 μM concentration displayed growth inhibition not only up to 99.74% as observed for 9a but also a lethal effect could be achieved as stated for compounds 9c (RPMI-8226 and HCT-116) and 8b, 9a, and 9e on the HCT-116 cell line. The antiproliferative activity was determined for the chalcone series on three cell lines: RPMI-8226, HCT-116, and MCF-7. Compounds 8b, 9a, 9b, and 9f were the most active ones. To understand the mechanistic study, the inhibitory effect on the epidermal growth factor receptor (EGFR) kinase was evaluated. The results stated that the activity of compound 8b (IC 50  = 0.07 μM) was near that of the reference drug erlotinib (IC 50  = 0.052 μM) whereas compound 9b (IC 50  = 0.045 μM) was found to be more potent than erlotinib. Both compounds 8b and 9b were selected for cell cycle analysis and apoptotic assays. Moreover, molecular docking results of the selected chalcone hybrids showed high binding scores and good binding affinities especially for 8b and 9b, which were consistent with the biological activity (EGFR).
(© 2024 Deutsche Pharmazeutische Gesellschaft.)
References: World Health Organization, https://www.who.int/news-room/fact-sheets/detail/cancer (accessed: June 2023).
Brianna, S. H. Lee, Med. Oncol. 2023, 40(3), 88.
R. Bansal, A. Malhotra, Eur. J. Med. Chem. 2021, 211, 113016.
P. Bhatia, V. Sharma, O. Alam, A. Manaithiya, P. Alam, Kahksha, M. T. Alam, M. Imran, Eur. J. Med. Chem. 2020, 204, 112640.
A. M. Emam, A. Dahal, S. S. Singh, R. D. Tosso, S. M. Ibrahim, M. El‐Sadek, S. D. Jois, R. D. Enriz, H. Kothayer, Arch. Pharm. (Weinheim) 2021, 354(12), e2100281.
R. Aggarwal, G. Sumran, Eur. J. Med. Chem. 2020, 205, 112652.
A. A. WalyEldeen, S. Sabet, H. M. El‐Shorbagy, I. A. Abdelhamid, S. A. Ibrahim, Chem. Biol. Interact. 2023, 369, 110297.
M. M. Amin, G. E. D. A. Abuo‐Rahma, M. S. A. Shaykoon, A. A. Marzouk, M. A. S. Abourehab, R. E. Saraya, M. Badr, A. M. Sayed, E. A. M. Beshr, Bioorg. Chem. 2023, 134, 106444.
J. Nawaz, A. Rasul, M. A. Shah, G. Hussain, A. Riaz, I. Sarfraz, S. Zafar, M. Adnan, A. H. Khan, Z. Selamoglu, Life. Sci. 2020, 250, 117591.
M. Wang, L. Lin, J. J. Lu, X. Chen, Pharmacol. Res. 2021, 165, 105483.
A. E. Abdallah, I. H. Eissa, A. B. M. Mehany, H. Sakr, A. Atwa, K. El‐Adl, M. A. El‐Zahabi, J. Mol. Struct. 2023, 1281, 135164.
A. M. Soliman, M. M. Ghorab, Bioorg. Chem. 2019, 88, 102956.
H. A. Abou‐Zied, B. G. M. Youssif, M. F. A. Mohamed, A. M. Hayallah, M. Abdel‐Aziz, Bioorg. Chem. 2019, 89, 102997.
M. Hisham, H. A. Hassan, H. A. M. Gomaa, B. G. M. Youssif, A. M. Hayallah, M. Abdel‐Aziz, J. Mol. Struct. 2022, 1254, 132422.
F. F. Ahmed, A. A. Abd El‐Hafeez, S. H. Abbas, D. Abdelhamid, M. Abdel‐Aziz, Eur. J. Med. Chem. 2018, 151, 705.
A. M. Mohassab, H. A. Hassan, D. Abdelhamid, A. M. Gouda, B. G. M. Youssif, H. Tateishi, M. Fujita, M. Otsuka, M. Abdel‐Aziz, Bioorg. Chem. 2021, 106, 104510.
W. A. Ewes, M. A. Elmorsy, S. M. El‐Messery, M. N. A. Nasr, Bioorg. Med. Chem. 2020, 28(7), 115373.
H. Kothayer, S. Rezq, A. S. Abdelkhalek, D. G. Romero, S. S. Elbaramawi, J. Enzyme Inhib. Med. Chem. 2023, 38(1), 2199166.
H. M. Moustafa, Phosphorus Sulfur Silicon Relat. Elem. 2000, 164(1), 11.
L. Chunying Luo, P. Li, H. Liu, P. Feng, J. Li, L. Zhao, C.‐L. Wu, Russ. J. Bioorg. Chem. 2020, 46(2), 139.
M. Gomes, E. Muratov, M. Pereira, J. Peixoto, L. Rosseto, P. Cravo, C. Andrade, B. Neves, Molecules 2017, 22(8), 1210.
NCI D.T.P. National Cancer Institute, https://www.dtp.cancer.gov/discovery&#95;development/nci-60/methodology.htm (accessed: April 2022).
T. Mosmann, J. Immunol. Methods 1983, 65(1–2), 55.
F. Denizot, R. Lang, J. Immunol. Methods 1986, 89(2), 271.
W. Liu, X. Wu, W. Zhang, R. C. Montenegro, D. L. Fackenthal, J. A. Spitz, L. M. Huff, F. Innocenti, S. Das, E. H. Cook Jr., N. J. Cox, S. E. Bates, M. J. Ratain, Clin. Cancer Res. 2007, 13(22 Pt 1), 6788.
L. Rao, D. Giannico, P. Leone, A. G. Solimando, E. Maiorano, C. Caporusso, L. Duda, R. Tamma, R. Mallamaci, N. Susca, A. Buonavoglia, M. C. Da Vià, D. Ribatti, V. De Re, A. Vacca, V. Racanelli, Cancers 2020, 12(1), 173.
A. M. Krasinskas, Patholog. Res. Int. 2011, 2011, 1.
R. Garcia, R. A. Franklin, J. A. McCubrey, Cell Cycle 2006, 5(16), 1840.
M. A. Mansour, A. M. AboulMagd, S. H. Abbas, M. Abdel‐Aziz, H. M. Abdel‐Rahman, Arch. Pharm. 2024, e2300626, https://doi.org/10.1002/ardp.202300626.
A. A. Gaber, M. Sobhy, A. Turky, W. M. Eldehna, S. A. El‐Sebaey, S. A. El‐Metwally, A. M. El‐Naggar, I. M. Ibrahim, E. B. Elkaeed, A. M. Metwaly, I. H. Eissa, PLoS One 2023, 18(1), e0274081.
E. R. Mohammed, G. F. Elmasry, J. Enzyme Inhib. Med. Chem. 2022, 37(1), 686.
A. Kamal, A. Mallareddy, P. Suresh, V. Lakshma Nayak, R. V. C. R. N. C. Shetti, N. Sankara Rao, J. R. Tamboli, T. B. Shaik, M. V. P. S. Vishnuvardhan, S. Ramakrishna, Eur. J. Med. Chem. 2012, 47(1), 530.
J. Stamos, M. X. Sliwkowski, C. Eigenbrot, J. Biol. Chem. 2002, 277(48), 46265.
Y. Jia, C. M. Quinn, A. I. Gagnon, R. Talanian, Anal. Biochem. 2006, 356(2), 273.
H. A. El‐Mahdy, A. A. El‐Husseiny, Y. I. Kandil, A. M. Gamal El‐Din, Life. Sci. 2020, 262, 118518.
A. A. Nasser, I. H. Eissa, M. R. Oun, M. A. El‐Zahabi, M. S. Taghour, A. Belal, A. M. Saleh, A. B. M. Mehany, H. Luesch, A. E. Mostafa, W. M. Afifi, J. R. Rocca, H. A. Mahdy, Org. Biomol. Chem. 2020, 18(38), 7608.
Molecular Operating Environment (MOE 2019.0102). Chemical Computing Group Inc, Montreal Quebec Canada. http://www.chemcomp.com.2019.0102.
فهرسة مساهمة: Keywords: EGFR inhibitors; apoptotic inducers; chalcone; dual activity; triazoloquinazoline hybrids
المشرفين على المادة: EC 2.7.10.1 (ErbB Receptors)
0 (Antineoplastic Agents)
0 (Quinazolines)
EC 2.7.10.1 (EGFR protein, human)
0 (Triazoles)
0 (Protein Kinase Inhibitors)
0 (Chalcones)
288-88-0 (1,2,4-triazole)
0 (Acetamides)
5S5A2Q39HX (Chalcone)
تواريخ الأحداث: Date Created: 20240409 Date Completed: 20240703 Latest Revision: 20240709
رمز التحديث: 20240709
DOI: 10.1002/ardp.202300627
PMID: 38593298
قاعدة البيانات: MEDLINE
الوصف
تدمد:1521-4184
DOI:10.1002/ardp.202300627