Triazolopyridazine derivatives: Synthesis, cytotoxic evaluation, c-Met kinase activity and molecular docking

Show simple item record

dc.contributor.author Ahmed E.M.
dc.contributor.author Khalil N.A.
dc.contributor.author Taher A.T.
dc.contributor.author Refaey R.H.
dc.contributor.author Nissan Y.M.
dc.contributor.other Pharmaceutical Organic Chemistry Department
dc.contributor.other Faculty of Pharmacy
dc.contributor.other Cairo University
dc.contributor.other Cairo
dc.contributor.other Egypt; Pharmaceutical Organic Chemistry Department
dc.contributor.other Faculty of Pharmacy
dc.contributor.other October 6 University
dc.contributor.other Giza
dc.contributor.other Egypt; Pharmaceutical Chemistry Department
dc.contributor.other Faculty of Pharmacy
dc.contributor.other October University for Modern Sciences and Arts (MSA)
dc.contributor.other Giza
dc.contributor.other Egypt; Pharmaceutical Chemistry Department
dc.contributor.other Faculty of Pharmacy
dc.contributor.other Cairo University
dc.contributor.other Kasr Elini St.
dc.contributor.other Cairo
dc.contributor.other 11562
dc.contributor.other Egypt
dc.date.accessioned 2020-01-09T20:40:31Z
dc.date.available 2020-01-09T20:40:31Z
dc.date.issued 2019
dc.identifier.issn 452068
dc.identifier.other https://doi.org/10.1016/j.bioorg.2019.103272
dc.identifier.other PubMed ID 31539742
dc.identifier.uri https://t.ly/AXqNp
dc.description Scopus
dc.description.abstract Novel series of some triazolo[4,3-b]pyridazine derivatives were designed and synthesized. All the newly synthesized compounds were evaluated for their cytotoxic activity at 10?5 M concentration towards 60 cancer cell lines according to USA NCI protocol. Most of the synthesized compounds showed good activity against SR (leukemia) cell panel. The most active compounds, 2f and 4a were subjected for further evaluation at a five dose level screening and their efficacy for c-Met kinase inhibition was determined in vitro. Binding mode of these derivatives was explored via molecular docking. 2019 Elsevier Inc. en_US
dc.description.uri https://www.scimagojr.com/journalsearch.php?q=25789&tip=sid&clean=0
dc.language.iso English en_US
dc.publisher Academic Press Inc. en_US
dc.relation.ispartofseries Bioorganic Chemistry
dc.relation.ispartofseries 92
dc.subject c-Met kinase en_US
dc.subject Cytotoxic activity en_US
dc.subject Pyridazines en_US
dc.subject Triazolopyridazines en_US
dc.subject cytotoxic agent en_US
dc.subject phosphotransferase inhibitor en_US
dc.subject scatter factor receptor en_US
dc.subject triazolopyridazine derivative en_US
dc.subject antineoplastic activity en_US
dc.subject Article en_US
dc.subject breast cancer en_US
dc.subject cancer inhibition en_US
dc.subject central nervous system cancer en_US
dc.subject colon cancer en_US
dc.subject controlled study en_US
dc.subject drug binding en_US
dc.subject drug efficacy en_US
dc.subject drug screening en_US
dc.subject drug synthesis en_US
dc.subject enzyme activity en_US
dc.subject enzyme inhibition en_US
dc.subject GI50 en_US
dc.subject human en_US
dc.subject human cell en_US
dc.subject IC50 en_US
dc.subject in vitro study en_US
dc.subject kidney cancer en_US
dc.subject leukemia en_US
dc.subject melanoma en_US
dc.subject molecular docking en_US
dc.subject non small cell lung cancer en_US
dc.subject ovary cancer en_US
dc.subject priority journal en_US
dc.subject prostate cancer en_US
dc.subject proton nuclear magnetic resonance en_US
dc.subject structure activity relation en_US
dc.title Triazolopyridazine derivatives: Synthesis, cytotoxic evaluation, c-Met kinase activity and molecular docking en_US
dc.type Article en_US
dcterms.isReferencedBy Liu, X., Yao, W., Newton, R.C., Scherle, P.A., Targeting the c-MET signaling pathway for cancer therapy (2008) Exp. Opin. Invest. Drugs, 17 (7), pp. 997-1011; Schmidt, C., Bladt, F., Goedecke, S., Brinkmann, V., Zschiesche, W., Sharpe, M., Gherardi, E., Birchmeler, C., Scatter factor/hepatocyte growth factor is essential for liver development (1995) Nature, 373 (6516), p. 699; Uehara, Y., Minowa, O., Mori, C., Shiota, K., Kuno, J., Noda, T., Kitamura, N., Placental defect and embryonic lethality in mice lacking hepatocyte growth factor/scatter factor (1995) Nature, 373 (6516), p. 702; Kawaida, K., Matsumoto, K., Shimazu, H., Nakamura, T., Hepatocyte growth factor prevents acute renal failure and accelerates renal regeneration in mice (1994) PNAS, 91 (10), pp. 4357-4361; Nakamura, T., Mizuno, S., Matsumoto, K., Sawa, Y., Matsuda, H., Nakamura, T., Myocardial protection from ischemia/reperfusion injury by endogenous and exogenous HGF (2000) J. Clin. Investig., 106 (12), pp. 1511-1519; Tsubouchi, H., Niitani, Y., Hirono, S., Nakayama, H., Gohda, E., Arakaki, N., Sakiyama, O., Kawakami, S., Levels of the human hepatocyte growth factor in serum of patients with various liver diseases determined by an enzyme-linked immunosorbent assay (1991) Hepatology, 13 (1), pp. 1-5; Birchmeier, C., Birchmeier, W., Gherardi, E., Vande Woude, G.F., Met, metastasis, motility and more (2003) Nat. Rev. Mol. Cell Biol., 4, p. 915; Maroun, C.R., Rowlands, T., The Met receptor tyrosine kinase: a key player in oncogenesis and drug resistance (2014) Pharmacol. Ther., 142 (3), pp. 316-338; Comoglio, P.M., Giordano, S., Trusolino, L., Drug development of MET inhibitors: targeting oncogene addiction and expedience (2008) Nat. Rev. Drug Discov., 7, p. 504; Sun, Z.-G., Yang, Y.-A., Zhang, Z.-G., Zhu, H.-L., Optimization techniques for novel c-Met kinase inhibitors (2019) Exp. Opin. Drug Discov., 14 (1), pp. 59-69; Malik, S.M., Maher, V.E., Bijwaard, K.E., Becker, R.L., Zhang, L., Tang, S.W., Song, P., Pazdur, R., U.S. Food and Drug Administration Approval: Crizotinib for treatment of advanced or metastatic non-small cell lung cancer that is anaplastic lymphoma kinase positive (2014) Clin. Canc. Res., 20 (8), pp. 2029-2034; Rimassa, L., Assenat, E., Peck-Radosavljevic, M., Pracht, M., Zagonel, V., Mathurin, P., Rota Caremoli, E., Bruix, J., Tivantinib for second-line treatment of MET-high, advanced hepatocellular carcinoma (METIV-HCC): a final analysis of a phase 3, randomised, placebo-controlled study (2018) Lancet Oncol., 19 (5), pp. 682-693; Traynor, K., Cabozantinib approved for advanced medullary thyroid cancer (2013) Am. J. Health Syst. Pharm., 70 (2), p. 88; Yau, T.C.C., Lencioni, R., Sukeepaisarnjaroen, W., Chao, Y., Yen, C.-J., Lausoontornsiri, W., Chen, P.-J., Bottaro, D.P., A phase I/II multicenter study of single-agent foretinib as first-line therapy in patients with advanced hepatocellular carcinoma (2017) Clin. Canc. Res. Off. J. Am. Assoc. Canc. Res., 23 (10), pp. 2405-2413; Albrecht, B.K., Harmange, J.-C., Bauer, D., Berry, L., Bode, C., Boezio, A.A., Chen, A., Fridrich, C., Discovery and optimization of triazolopyridazines as potent and selective inhibitors of the c-Met kinase (2008) J. Med. Chem., 51 (10), pp. 2879-2882; Boezio, A.A., Berry, L., Albrecht, B.K., Bauer, D., Bellon, S.F., Bode, C., Chen, A., Harmange, J.-C., Discovery and optimization of potent and selective triazolopyridazine series of c-Met inhibitors (2009) Bioorg. Med. Chem. Lett., 19 (22), pp. 6307-6312; Ryu, J.W., Han, S.-Y., Yun, J.I., Choi, S.-U., Jung, H., Ha, J.D., Cho, S.Y., Lee, J., Design and synthesis of triazolopyridazines substituted with methylisoquinolinone as selective c-Met kinase inhibitors (2011) Bioorg. Med. Chem. Lett., 21 (23), pp. 7185-7188; Sattler, M., Hasina, R., Reddy, M.M., Gangadhar, T., Salgia, R., The role of the c-Met pathway in lung cancer and the potential for targeted therapy (2011) Therap. Adv. Med. Oncol., 3 (4), pp. 171-184; Underiner, T.L., Herbertz, T., Miknyoczki, S.J., Discovery of small molecule c-Met inhibitors: evolution and profiles of clinical candidates, anti-cancer agents in medicinal (2010) Chem.- Anti-Cancer Age., 10 (1), pp. 7-27; Buchanan, S.G., Hendle, J., Lee, P.S., Smith, C.R., Bounaud, P.-Y., Jessen, K.A., Tang, C.M., Reich, S.H., SGX523 is an exquisitely selective, ATP-competitive inhibitor of the MET receptor tyrosine kinase with antitumor activity in vivo (2009) Mol. Cancer Ther., 8 (12), pp. 3181-3190; Abouzid, K.A.M., Khalil, N.A., Ahmed, E.M., Esmat, A., Al-Abd, A.M., Design, synthesis, and evaluation of anti-inflammatory and ulcerogenicity of novel pyridazinone derivatives (2012) Med. Chem. Res., 21 (11), pp. 3581-3590; Abouzid, K.A.M., Khalil, N.A., Ahmed, E.M., Mohamed, K.O., 3-[(6-Arylamino)pyridazinylamino]benzoic acids: design, synthesis and in vitro evaluation of anticancer activity (2013) Arch. Pharm. Res., 36 (1), pp. 41-50; Rostom, S.A., Synthesis and in vitro antitumor evaluation of some indeno [1, 2-c] pyrazol (in) es substituted with sulfonamide, sulfonylurea (-thiourea) pharmacophores, and some derived thiazole ring systems (2006) Bioorg. Med. Chem., 14 (19), pp. 6475-6485; Furlan, A., Colombo, F., Kover, A., Issaly, N., Tintori, C., Angeli, L., Leroux, V., Maina, F., Identification of new aminoacid amides containing the imidazo[2,1-b]benzothiazol-2-ylphenyl moiety as inhibitors of tumorigenesis by oncogenic Met signaling (2012) Eur. J. Med. Chem., 47, pp. 239-254; Rasmussen, J.T., Petiwala, S.M., Johnson, J.J., Kohl, A.M., Syed, D.N., Mukhtar, H., Siddiqui, I.A., Adhami, V.M., ?-Mangostin, a xanthone from mangosteen fruit, promotes cell cycle arrest in prostate cancer and decreases xenograft tumor growth (2011) Carcinogenesis, 33 (2), pp. 413-419; Porter, J., Small molecule c-Met kinase inhibitors: a review of recent patents (2010) Exp. Opin. Ther. Pat., 20 (2), pp. 159-177; Gherardi, E., Birchmeier, W., Birchmeier, C., Woude, G.V., Targeting MET in cancer: rationale and progress (2012) Nat. Rev. Cancer, 12 (2), p. 89; Boyd, M.R., Paull, K.D., Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen (1995) Drug Dev. Res., 34 (2), pp. 91-109; Grever, M.R., Schepartz, S.A., Chabner, B.A., The National Cancer Institute: cancer drug discovery and development program (1992) Semin. Oncol., 19 (6), pp. 622-638; Monks, A., Vaigro-Wolff, A., Hose, C., Scudiero, D., Campbell, H., Langley, J., Gray-Goodrich, M., Shoemaker, R., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines (1991) JNCI: J. Natl. Canc. Instit., 83 (11), pp. 757-766; Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Boyd, M.R., New colorimetric cytotoxicity assay for anticancer-drug screening (1990) JNCI: J. Natl. Cancer Instit., 82 (13), pp. 1107-1112; Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J., AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility (2009) J. Comput. Chem., 30 (16), pp. 2785-2791; Berman, H.M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T.N., Weissig, H., Shindyalov, I.N., Bourne, P.E., The protein data bank (2000) Nucl. Acids Res., 28 (1), pp. 235-242; Pettersen, E.F., Goddard, T.D., Huang, C.C., Couch, G.S., Greenblatt, D.M., Meng, E.C., Ferrin, T.E., UCSF Chimeraa visualization system for exploratory research and analysis (2004) J. Comput. Chem., 25 (13), pp. 1605-1612
dcterms.source Scopus
dc.identifier.doi https://doi.org/10.1016/j.bioorg.2019.103272
dc.identifier.doi PubMed ID 31539742
dc.Affiliation October University for modern sciences and Arts (MSA)


Files in this item

This item appears in the following Collection(s)

Show simple item record

Search MSAR


Advanced Search

Browse

My Account