Synthesis, anticancer evaluation and molecular docking studies of new benzimidazole- 1,3,4-oxadiazole derivatives as human topoisomerase types I poison

References

• Singh R, Pandey S, Sur S, et al. PPEF: A bisbenzimdazole potent antimicrobial agent interacts at acidic triad of catalytic domain of E. coli topoisomerase IA. Biochim Biophys Acta Gen Subj 2019;1863:1524–35.
   PubMed Web of Science ®Google Scholar
• Liang X, Wu Q, Luan S, et al. A comprehensive review of topoisomerase inhibitors as anticancer agents in the past decade. Eur J Med Chem 2019;171:129–68.
   PubMed Web of Science ®Google Scholar
• Bansal S, Sur S, Tandon V. Benzimidazoles: Selective inhibitors of topoisomerase I with differential modes of action. Biochemistry 2019;58:809–17.
   PubMed Web of Science ®Google Scholar
• Halawa AH, Elgammal WE, Hassan SM, et al. Synthesis, anticancer evaluation and molecular docking studies of new heterocycles linked to sulfonamide moiety as novel human topoisomerase types I and II poisons. Bioorg. Chem 2020;98:103725.
   PubMed Web of Science ®Google Scholar
• Mohamady S, Gibriel AA, Ahmed MS, et al. Design and novel synthetic approach supported with molecular docking and biological evidence for naphthoquinone-hydrazinotriazolothiadiazine analogs as potential anticancer inhibiting topoisomerase-IIB. Bioorg. Chem 2020;96:103641.
   PubMed Web of Science ®Google Scholar
• Issar U, Arora R, Kumari T, et al. Combined pharmacophore-guided 3D-QSAR, molecular docking, and virtual screening on bis-benzimidazoles and ter-benzimidazoles as DNA–topoisomerase I poisons. Struct. Chem 2019;30:1185–201.
   Web of Science ®Google Scholar
• Shu B, Yu Q, Hu DX, et al. Synthesis and biological evaluation of novel indole-pyrazoline hybrid derivatives as potential topoisomerase 1 inhibitors. Bioorg Med Chem Lett 2020;30:126925.
   PubMed Web of Science ®Google Scholar
• Sharma PC, Bansal KK, Sharma A, et al. Thiazole-containing compounds as therapeutic targets for cancer therapy. Eur J Med Chem 2020;188:112016.
   PubMed Web of Science ®Google Scholar
• Lee JF, Chang TY, Liu ZF, et al. Design, synthesis, and biological evaluation of heterotetracyclic quinolinone derivatives as anticancer agents targeting topoisomerases. Eur. J. Med. Chem 2020;190:112074.
   PubMed Web of Science ®Google Scholar
• Joshi G, Kalra S, Yadav UP, et al. E-pharmacophore guided discovery of pyrazolo [1,5-c] quinazolines as dual inhibitors of topoisomerase-I and histone deacetylase. Bioorg. Chem 2020;94:103409.
   PubMed Web of Science ®Google Scholar
• K Kathiravan M, N Kale A, Nilewar S. Discovery and development of topoisomerase inhibitors as anticancer agents. Mini Rev Med Chem 2016;16:1219–29.
   PubMed Web of Science ®Google Scholar
• Aichinger G, Lichtenberger FB, Steinhauer TN, et al. The Aza-Analogous Benzo [c] phenanthridine P8-D6 Acts as a Dual Topoisomerase I and II Poison, thus Exhibiting Potent Genotoxic Properties. Molecules 2020;25:1524.
   Web of Science ®Google Scholar
• Lian C, Cao S, Zeng W, et al. RJT-101, a novel camptothecin derivative, is highly effective in the treatment of melanoma through DNA damage by targeting topoisomerase 1. Biochem Pharmacol 2020;171:113716.
   PubMed Web of Science ®Google Scholar
• Dehshahri A, Ashrafizadeh M, Afshar EG, et al. Topoisomerase inhibitors: Pharmacology and emerging nanoscale delivery systems. Pharmacol. Res 2020;151:104551.
   PubMed Web of Science ®Google Scholar
• Nunhart P, Konkoľová E, Janovec L, et al. Fluorinated 3,6,9-trisubstituted acridine derivatives as DNA interacting agents and topoisomerase inhibitors with A549 antiproliferative activity. Bioorg Chem 2020;94:103393.
   PubMed Web of Science ®Google Scholar
• Liu XW, Tang YC, Liu NY, et al. Topo I inhibition, DNA photocleavage, Molecular docking and cytotoxicities of two new phenanthroline‐based ruthenium complexes. Appl Organomet Chem 2020;34:e5312.
   Web of Science ®Google Scholar
• Alonso C, Fuertes M, Martín-Encinas E, et al. Novel topoisomerase I inhibitors. Syntheses and biological evaluation of phosphorus substituted quinoline derivates with antiproliferative activity. Eur J Med Chem 2018;149:225–37.
   PubMed Web of Science ®Google Scholar
• Sović I, Jambon S, Pavelić SK, et al. Synthesis, antitumor activity and DNA binding features of benzothiazolyl and benzimidazolyl substituted isoindolines. Bioorg Med Chem 2018;26:1950–60.
   PubMed Web of Science ®Google Scholar
• Sheng C, Miao Z, Zhang W. New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors. Curr Med Chem 2011;18:4389–409.
   PubMed Web of Science ®Google Scholar
• Galal SA, Hegab KH, Hashem AM, et al. Synthesis and antitumor activity of novel benzimidazole-5-carboxylic acid derivatives and their transition metal complexes as topoisomerease II inhibitors. Eur J Med Chem 2010;45:5685–91.
   PubMed Web of Science ®Google Scholar
• Refaat HM. Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives. Eur J Med Chem 2010; 45:2949–56.
   PubMed Web of Science ®Google Scholar
• Romero-Castro A, León-Rivera I, Ávila-Rojas LC, et al. Synthesis and preliminary evaluation of selected 2-aryl-5(6)-nitro- 1H-benzimidazole derivatives as potential anticancer agents. Arch Pharm Res 2011;34:181–9.
   PubMed Web of Science ®Google Scholar
• Abonia R, Cortés E, Insuasty B, et al. Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents. Eur J Med Chem 2011;46:4062–70.
   PubMed Web of Science ®Google Scholar
• Rashid M, Husain A, Mishra R, et al. Design and synthesis of benzimidazoles containing substituted oxadiazole, thiadiazole and triazolo-thiadiazines as a source of new anticancer agents. Arab J Chem 2019;12:3202–24.
   Web of Science ®Google Scholar
• Sunke R, Babu PV, Yellanki S, et al. Ligand-free MCR for linking quinoxaline framework with a benzimidazole nucleus: a new strategy for the identification of novel hybrid molecules as potential inducers of apoptosis. Org Biomol Chem 2014;12:6800–5.
   PubMed Web of Science ®Google Scholar
• Rashid M, Husain A, Mishra R. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents. Eur J Med Chem 2012;54:855–66.
   PubMed Web of Science ®Google Scholar
• Rao VM, Rao AS, Rani SS, et al. Ultrasound assisted cu-catalyzed synthesis of 1,2-disubstituted benzimidazoles as potential antibacterial agents. Mini Rev Med Chem 2018;18:1233–9.
   PubMed Web of Science ®Google Scholar
• Formagio ASN, Tonin LTD, Foglio MA, et al. Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl) β-carboline derivatives. Bioorg Med Chem 2008;16:9660–7.
   PubMed Web of Science ®Google Scholar
• Glomb T, Szymankiewicz K, Świątek P. Anti-cancer activity of derivatives of 1,3,4-oxadiazole. Molecules 2018;23:3361.
   PubMed Web of Science ®Google Scholar
• Neeraja P, Srinivas S, Mukkanti K, et al. 1H-1,2,3-Triazolyl-substituted 1,3,4-oxadiazole derivatives containing structural features of ibuprofen/naproxen: Their synthesis and antibacterial evaluation. Bioorg Med Chem Lett 2016;26:5212–7.
   PubMed Web of Science ®Google Scholar
• Mochona B, Mazzio E, Gangapurum M, et al. Synthesis of some benzimidazole derivatives bearing 1,3,4-oxadiazole moiety as anticancer agents. Chem Sci Trans 2015;4:534–40.
   PubMedGoogle Scholar
• Çevik UA, Osmaniye D, Çavuşoğlu BK, et al. Synthesis of novel benzimidazole–oxadiazole derivatives as potent anticancer activity. Med Chem Res 2019;28:2252–61.
   Web of Science ®Google Scholar
• Evren AE, Yurttaş L, Eksellı B, et al. Novel Tri-substituted Thiazoles Bearing Piperazine Ring: Synthesis and Evaluation of their Anticancer Activity. Lett Drug Des. Discov 2019;16:547–55.
   Web of Science ®Google Scholar
• Acar Çevik U, Sağlık BN, Korkut B, et al. Antiproliferative, cytotoxic, and apoptotic effects of new benzimidazole derivatives bearing hydrazone moiety. J Heterocyc Chem 2018;55:138–48.
   Web of Science ®Google Scholar
• Staker BL, Feese MD, Cushman M, et al. Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex. J Med Chem 2005;48:2336–45.
   PubMed Web of Science ®Google Scholar
• Maestro, version 10.6, Schrödinger, LLC, New York, NY, 2016.
   Google Scholar
• Schrödinger LLC, New York, NY, 2016.
   Google Scholar
• LigPrep, version 3.8, Schrödinger, LLC, New York, NY, 2016.
   Google Scholar
• Glide, version 7.1, Schrödinger, LLC, New York, NY, 2016.
   Google Scholar
• Oksuzoglu E, Tekıner-Gulbas B, Alper S, et al. Some benzoxazoles and benzimidazoles as DNA topoisomerase I and II inhibitors. J Enzyme Inhib Med Chem 2008;23:37–42.
   PubMed Web of Science ®Google Scholar
• Foto E, Özen Ç, Zilifdar F, et al. Benzoxazines as new human topoisomerase I inhibitors and potential poisons. DARU J Pharma Sci 2019;28:65–73.
   Web of Science ®Google Scholar
• Xu Y, Wu L, Rashid HU, et al. Novel indolo-sophoridinic scaffold as Topo I inhibitors: Design, synthesis and biological evaluation as anticancer agents. Eur J Med Chem 2018;156:479–92.
   PubMed Web of Science ®Google Scholar
• Xu Y, Jing D, Chen R, et al. Design, synthesis and evaluation of novel sophoridinic imine derivatives containing conjugated planar structure as potent anticancer agents. Bioorg. Med. Chem 2018;26:4136–44.
   PubMed Web of Science ®Google Scholar
• Arepalli SK, Lee C, Sim S, et al. Development of 13H-benzo [f] chromeno [4,3-b][1,7] naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors. Bioorg. Med. Chem 2018;26:5181–93.
   PubMed Web of Science ®Google Scholar
• Arthur DE, Uzairu A. Molecular docking study and structure‐based design of novel camptothecin analogues used as topoisomerase I inhibitor. J Chin Chem Soc 2018;65:1160–78.
   Web of Science ®Google Scholar