title: Study of reactivity of cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzenesulfonamide: preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase.
abstract: This article describes the synthesis of some novel heterocyclic sulfonamides having biologically active thiophene 3, 4, 5, 6, coumarin 8, benzocoumarin 9, thiazole 7, piperidine 10, pyrrolidine 11, pyrazole 14 and pyridine 12, 13. Starting with 4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)-N-ethyl-N-methylbenzenesulfonamide (2), which was prepared from condensation of acetophenone derivative 1 with 2-cyanoacetohydrazide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR,1H NMR,13C NMR,19F NMR and MS spectral data. All the newly synthesized heterocyclic sulfonamides were evaluated as in-vitro anti-breast cancer cell line (MCF7) and as in-vitro antimicrobial agents. Compounds 8, 5 and 11 were more active than MTX reference drug and compounds 12, 7, 4, 14, 5 and 8 were highly potent against Klebsiella pneumonia. Molecular operating environment performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some prepared compounds are suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDBSD:4DFR) with further modification.
authors.affiliation: a Department of Chemistry , University College in Al-Jamoum, Umm Al-Qura University , Makkah , Saudi Arabia.|b Laboratory of Heterocyclic Chemistry , Natural Products and Reactivity, Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir , Tunisia.
authors.forename: Khaled F
authors.initials: KF
authors.lastname: Debbabi
authors.affiliation: a Department of Chemistry , University College in Al-Jamoum, Umm Al-Qura University , Makkah , Saudi Arabia.
authors.forename: Sami A
authors.initials: SA
authors.lastname: Al-Harbi
authors.affiliation: a Department of Chemistry , University College in Al-Jamoum, Umm Al-Qura University , Makkah , Saudi Arabia.
authors.forename: Hamed M
authors.initials: HM
authors.lastname: Al-Saidi
authors.affiliation: c Department of Chemistry , College of Applied Science, Umm Al-Qura University , Makkah , Saudi Arabia.
authors.forename: Enas H
authors.initials: EH
authors.lastname: Aljuhani
authors.affiliation: d Deparment of Organic Chemistry , Faculty of Pharmacy (Girls), Al-Azhar University, Nasr City, Cairo, Egypt , and.
authors.forename: Shimaa M
authors.initials: SM
authors.lastname: Abd El-Gilil
authors.affiliation: a Department of Chemistry , University College in Al-Jamoum, Umm Al-Qura University , Makkah , Saudi Arabia.|e Chemistry Department, Faculty of Science (Boys), Al-Azhar University , Nasr City , Cairo , Egypt.
authors.forename: Mahmoud S
authors.initials: MS
authors.lastname: Bashandy
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005493:Folic Acid Antagonists / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007711:Klebsiella pneumoniae / Q000187:drug effects*; D061986:MCF-7 Cells; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013762:Tetrahydrofolate Dehydrogenase / Q000378:metabolism*; D000096926:Benzenesulfonamides
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D005493:Folic Acid Antagonists; D009570:Nitriles; D013449:Sulfonamides; D013762:Tetrahydrofolate Dehydrogenase; C000614254:cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzenesulfonamide; D000096926:Benzenesulfonamides
keywords: Anticancer; antimicrobial; cytotoxicity; heterocyclic sulfonamides; molecular docking