Design, synthesis, and apoptotic antiproliferative action of new 1,2,3-triazole/1,2,4-oxadiazole hybrids as dual EGFR/VEGFR-2 inhibitors

References

• Akram M, Iqbal M, Daniyal M, Khan AU. Awareness and current knowledge of breast cancer. Biol Res. 2017;50(1):33.
   PubMed Web of Science ®Google Scholar
• Youssif BGM, Abdelrahman MH, Abdelazeem AH, Abdelgawad MA, Ibrahim HM, Salem OIA, Mohamed MFA, Treambleau L, Bukhari SNA. Design, synthesis, mechanistic and histopathological studies of small-molecules of novel indole-2-carboxamides and pyrazino[1,2-a]indol-1 (2H)-ones as potential anticancer agents effecting the reactive oxygen species production. Eur J Med Chem. 2018;146:260–273.
   PubMed Web of Science ®Google Scholar
• Guo YJ, Pan WW, Liu SB, Shen ZF, Xu Y, Hu LL. ERK/MAPK signalling pathway and tumorigenesis. Exp Ther Med. 2020;19(3):1997–2007.
   PubMed Web of Science ®Google Scholar
• Zwick E, Bange J, Ullrich A. Receptor tyrosine kinase signalling as a target for cancer intervention strategies. Endocr Relat Cancer. 2001;8(3):161–173.
   PubMed Web of Science ®Google Scholar
• Huang L, Fu L. Mechanisms of resistance to EGFR tyrosine kinase inhibitors. Acta Pharm Sin B. 2015;5(5):390–401.
   PubMed Web of Science ®Google Scholar
• Yewale C, Baradia D, Vhora I, Patil S, Misra A. Epidermal growth factor receptor targeting in cancer: a review of trends and strategies. Biomaterials. 2013;34(34):8690–8707.
   PubMed Web of Science ®Google Scholar
• Mohamed FA, Gomaa HA, Hendawy O, Ali AT, Farghaly HS, Gouda AM, Abdelazeem AH, Abdelrahman MH, Trembleau L, Youssif BG. Design, synthesis, and biological evaluation of novel EGFR inhibitors containing 5-chloro-3-hydroxymethyl-indole-2-carboxamide scaffold with apoptotic antiproliferative activity. Bioorg Chem. 2021;112:104960.
   PubMed Web of Science ®Google Scholar
• Modi SJ, Kulkarni VM. Vascular endothelial growth factor receptor (VEGFR-2)/KDR inhibitors: medicinal chemistry perspective. Med Drug Discov. 2019;2:100009.
   Google Scholar
• Falcon BL, Chintharlapalli S, Uhlik MT, Pytowski B. Antagonist antibodies to vascular endothelial growth factor receptor 2 (VEGFR-2) as anti-angiogenic agents. Pharmacol Ther. 2016;164:204–225.
   PubMed Web of Science ®Google Scholar
• Peng F-W, Liu D-K, Zhang Q-W, Xu Y-G, Shi L. VEGFR-2 inhibitors and the therapeutic applications thereof: a patent review (2012–2016). Expert Opin Ther Pat. 2017;27(9):987–1004.
   PubMed Web of Science ®Google Scholar
• Lemmon MA, Schlessinger J. Cell signaling by receptor tyrosine kinases. Cell. 2010;141(7):1117–1134.
   PubMed Web of Science ®Google Scholar
• Liao JJ-L. Molecular recognition of protein kinase binding pockets for design of potent and selective kinase inhibitors. J Med Chem. 2007;50(3):409–424.
   PubMed Web of Science ®Google Scholar
• Wheler JJ, Janku F, Naing A, Li Y, Stephen B, Zinner R, Subbiah V, Fu S, Karp D, Falchook GS, et al. TP53 alterations correlate with response to VEGF/VEGFR inhibitors: implications for targeted therapeutics. Mol Cancer Ther. 2016;15(10):2475–2485.
   PubMed Web of Science ®Google Scholar
• Xie C, Wan X, Quan H, Zheng M, Fu L, Li Y, Lou L. Preclinical characterization of anlotinib, a highly potent and selective vascular endothelial growth factor receptor‐2 inhibitor. Cancer Sci. 2018;109(4):1207–1219.
   PubMed Web of Science ®Google Scholar
• Liu Z-L, Chen H-H, Zheng L-L, Sun L-P, Shi L. Angiogenic signaling pathways and anti-angiogenic therapy for cancer. Signal Transduct Target Ther. 2023;8(1):198.
   PubMed Web of Science ®Google Scholar
• Sun S, Zhang J, Wang N, Kong X, Fu F, Wang H, Yao J. Design and discovery of quinazoline- and thiourea-containing sorafenib analogs as EGFR and VEGFR-2 dual TK inhibitors. Molecules. 2017;23(1):24.
   PubMed Web of Science ®Google Scholar
• Liu X-J, Zhao H-C, Hou S-J, Zhang H-J, Cheng L, Yuan S, Zhang L-R, Song J, Zhang S-Y, Chen S-W. Recent development of multi-target VEGFR-2 inhibitors for the cancer therapy. Bioorg Chem. 2023;133:106425.
   PubMed Web of Science ®Google Scholar
• Farghaly TA, Al-Hasani WA, Abdulwahab HG. An updated patent review of VEGFR-2 inhibitors (2017–present). Expert Opin Ther Pat. 2021;31(11):989–1007.
   PubMed Web of Science ®Google Scholar
• Zhang H-Q, Gong F-H, Li C-G, Zhang C, Wang Y-J, Xu Y-G, Sun L-P. Design and discovery of 4-anilinoquinazoline-acylamino derivatives as EGFR and VEGFR-2 dual TK inhibitors. Eur J Med Chem. 2016;109:371–379.
   PubMed Web of Science ®Google Scholar
• Biernacki K, Daśko M, Ciupak O, Kubiński K, Rachon J, Demkowicz S. Novel 1,2,4-oxadiazole derivatives in drug discovery. Pharmaceuticals. 2020;13(6):111.
   Web of Science ®Google Scholar
• Wang J-J, Sun W, Jia W-D, Bian M, Yu L-J. Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review. J Enzyme Inhib Med Chem. 2022;37(1):2304–2319.
   PubMed Web of Science ®Google Scholar
• Coupar I, Hedges A, Metcalfe HL, Turner P. Effect of aminophylline, butalamine and imolamine on human isolated smooth muscle. J Pharm Pharmacol. 1969;21(7):474–475.
   PubMed Web of Science ®Google Scholar
• Rotbart HA, Webster AD, Group PTR, Pleconaril Treatment Registry Group. Treatment of potentially life-threatening enterovirus infections with pleconaril. Clin Infect Dis. 2001;32(2):228–235.
   PubMed Web of Science ®Google Scholar
• McDonald CM, Campbell C, Torricelli RE, Finkel RS, Flanigan KM, Goemans N, Heydemann P, Kaminska A, Kirschner J, Muntoni F, Clinical Evaluator Training Group; ACT DMD Study Group, et al. Ataluren in patients with nonsense mutation Duchenne muscular dystrophy (ACT DMD): a multicentre, randomised, double-blind, placebo-controlled, phase 3 trial. Lancet. 2017;390(10101):1489–1498.
   PubMed Web of Science ®Google Scholar
• Dokla EM, Fang C-S, Abouzid KA, Chen CS. 1,2,4-Oxadiazole derivatives targeting EGFR and c-Met degradation in TKI resistant NSCLC. Eur J Med Chem. 2019;182:111607.
   PubMed Web of Science ®Google Scholar
• Venu K, Saritha B, Sailaja BBV. New molecular hybrids containing benzimidazole, thiazolidine-2,4-dione and 1,2,4-oxadiazole as EGFR directing cytotoxic agents. Tetrahedron. 2022;124:132991.
   Web of Science ®Google Scholar
• Mahmoud MA, Mohammed AF, Salem OI, Rabea SM, Youssif BG. Design, synthesis, and antiproliferative properties of new 1,2,3-triazole-carboximidamide derivatives as dual EGFR/VEGFR-2 inhibitors. J Mol Struct. 2023;1282:135165.
   Web of Science ®Google Scholar
• Al-Wahaibi LH, Mahmoud MA, Mostafa YA, Raslan AE, Youssif BG. Novel piperine-carboximidamide hybrids: design, synthesis, and antiproliferative activity via a multi-targeted inhibitory pathway. J Enzyme Inhib Med Chem. 2023;38 (1):376–386.
   PubMed Web of Science ®Google Scholar
• Al-Wahaibi LH, Mohammed AF, Abdel Rahman FE-ZS, Abdelrahman MH, Gu X, Trembleau L, Youssif BG. Design, synthesis, apoptotic, and antiproliferative effects of 5-chloro-3-(2-methoxyvinyl)-indole-2-carboxamides and pyrido[3,4-b]indol-1-ones as potent EGFRWT/EGFRT790M inhibitors. J Enzyme Inhib Med Chem. 2023;38(1):2218602.
   PubMed Web of Science ®Google Scholar
• El-Sheref EM, Bräse S, Tawfeek HN, Alasmary FA, Youssif BG. Synthesis, antioxidant and antiproliferative actions of 4-(1,2,3-triazol-1-yl)quinolin-2 (1H)-ones as multi-target inhibitors. Int J Mol Sci. 2023;24(17):13300.
   PubMed Web of Science ®Google Scholar
• Abdu-Allah HH, Youssif BG, Abdelrahman MH, Abdel-Hamid MK, Reshma RS, Yogeeswari P, Aboul-Fadl T, Sriram D. Synthesis and anti-mycobacterial activity of 4-(4-phenyl-1H-1,2,3-triazol-1-yl)salicylhydrazones: revitalizing an old drug. Arch Pharm Res. 2017;40(2):168–179.
   PubMed Web of Science ®Google Scholar
• Talukdar S, Hsu J-L, Chou T-C, Fang J-M. Direct transformation of aldehydes to nitriles using iodine in ammonia water. Tetrahedron Lett . 2001;42(6):1103–1105.
   Web of Science ®Google Scholar
• Frejat FOA, Zhai H, Cao Y, Wang L, Mostafa YA, Gomaa HA, Youssif BG, Wu C. Novel indazole derivatives as potent apoptotic antiproliferative agents by multi-targeted mechanism: synthesis and biological evaluation. Bioorg Chem. 2022;126:105922.
   PubMed Web of Science ®Google Scholar
• Gomaa HAM, Shaker ME, Alzarea SI, Hendawy OM, Mohamed FAM, Gouda AM, Ali AT, Morcoss MM, Abdelrahman MH, Trembleau L, et al. Optimization and SAR investigation of novel 2,3-dihydropyrazino[1,2-a]indole-1,4-dione derivatives as EGFR and BRAFV600E dual inhibitors with potent antiproliferative and antioxidant activities. Bioorg Chem. 2022;120:105616.
   PubMed Web of Science ®Google Scholar
• Gomaa HA, El-Sherief HA, Hussein S, Gouda AM, Salem OI, Alharbi KS, Hayallah AM, Youssif BG. Novel 1,2,4-triazole derivatives as apoptotic inducers targeting p53: synthesis and antiproliferative activity. Bioorg Chem. 2020;105:104369.
   PubMed Web of Science ®Google Scholar
• Youssif BG, Gouda AM, Moustafa AH, Abdelhamid AA, Gomaa HA, Kamal I, Marzouk AA. Design and synthesis of new triarylimidazole derivatives as dual inhibitors of BRAFV600E/p38α with potential antiproliferative activity. J Mol Struct. 2022;1253:132218.
   Web of Science ®Google Scholar
• Mekheimer RA, Allam SMR, Al-Sheikh MA, Moustafa MS, Al-Mousawi SM, Mostafa YA, Youssif BGM, Gomaa HAM, Hayallah AM, Abdelaziz M, et al. Discovery of new pyrimido[5,4-c]quinolines as potential antiproliferative agents with multitarget actions: rapid synthesis, docking, and ADME studies. Bioorg Chem. 2022;121:105693.
   PubMed Web of Science ®Google Scholar
• Mahmoud MA, Mohammed AF, Salem OI, Gomaa HA, Youssif BG. New 1,3,4‐oxadiazoles linked with the 1,2,3‐triazole moiety as antiproliferative agents targeting the EGFR tyrosine kinase. Arch Pharm (Weinheim). 2022;355(6):e2200009.
   PubMed Web of Science ®Google Scholar
• Marzouk AA, Abdel-Aziz SA, Abdelrahman KS, Wanas AS, Gouda AM, Youssif BG, Abdel-Aziz M. Design and synthesis of new 1,6-dihydropyrimidin-2-thio derivatives targeting VEGFR-2: molecular docking and antiproliferative evaluation. Bioorg Chem. 2020;102:104090.
   PubMed Web of Science ®Google Scholar
• Liu Y, Zhu X. Endoplasmic reticulum-mitochondria tethering in neurodegenerative diseases. Transl Neurodegener. 2017;6(1):21.
   PubMedGoogle Scholar
• Villa-Pulgarín JA, Gajate C, Botet J, Jimenez A, Justies N, Varela-M RE, Cuesta-Marbán Á, Müller I, Modolell M, Revuelta JL, et al. Mitochondria and lipid raft-located FOF1-ATP synthase as major therapeutic targets in the antileishmanial and anticancer activities of ether lipid edelfosine. PLoS Negl Trop Dis. 2017;11(8):e0005805.
   PubMed Web of Science ®Google Scholar
• Bao H, Zhang Q, Zhu Z, Xu H, Ding F, Wang M, Du S, Du Y, Yan Z. BHX, a novel pyrazoline derivative, inhibits breast cancer cell invasion by reversing the epithelial–mesenchymal transition and down-regulating Wnt/β-catenin signalling. Sci Rep. 2017;7(1):9153.
   PubMedGoogle Scholar
• Al-Wahaibi LH, Mostafa YA, Abdelrahman MH, El-Bahrawy AH, Trembleau L, Youssif BG. Synthesis and biological evaluation of indole-2-carboxamides with potent apoptotic antiproliferative activity as EGFR/CDK2 dual inhibitors. Pharmaceuticals. 2022;15(8):1006.
   Web of Science ®Google Scholar
• Choudhary GS, Al-Harbi S, Almasan A. Caspase-3 activation is a critical determinant of genotoxic stress-induced apoptosis. Methods Mol Biol. 2015;1219:1–9.
   PubMedGoogle Scholar
• Youssif BG, Mohamed AM, Osman EEA, Abou-Ghadir OF, Elnaggar DH, Abdelrahman MH, Treamblu L, Gomaa HA. 5-Chlorobenzofuran-2-carboxamides: from allosteric CB1 modulators to potential apoptotic antitumor agents. Eur J Med Chem. 2019;177:1–11.
   PubMed Web of Science ®Google Scholar
• Shattuck TW. Colby college molecular mechanics exercises MOE (molecular operating environment) exercises. Montreal, QC: Chemical Computing Group ULC; 2011.
   Google Scholar
• McTigue M, Murray BW, Chen JH, Deng Y-L, Solowiej J, Kania RS. Molecular conformations, interactions, and properties associated with drug efficiency and clinical performance among VEGFR TK inhibitors. Proc Natl Acad Sci U S A. 2012;109(45):18281–18289.
   PubMed Web of Science ®Google Scholar
• Daina A, Michielin O, Zoete VJ. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7(1):42717.
   PubMed Web of Science ®Google Scholar
• Pokhodylo NT, Savka RD, Shyyka OY, Obushak MD. One‐pot CuAAC synthesis of (1H‐1,2,3‐triazol‐1‐yl) methyl‐1,3,4/1,2,4‐oxadiazoles starting from available chloromethyl‐1,3,4/1,2,4‐oxadiazoles. J Heterocycl Chem. 2020;57(7):2969–2976.
   Web of Science ®Google Scholar