title: Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones.
abstract: A series of Mannich bases having piperidine moiety were reacted with 2-mercaptoethanol, leading to 1-aryl-3-piperidine-4-yl-1-propanone hydrochlorides. The cytotoxicity and carbonic anhydrase inhibitory activities of these new compounds were evaluated. Among the compounds, only one derivative, nitro substituent bearing EU9, showed an effective cytotoxicity, although weak tumor specificity against human oral malignant versus nonmalignant cells. The compound induced apoptosis in HSC-2 oral squamous cell carcinoma cells, but not in human gingival fibroblast. Chemical modifications of this lead are thus necessary to further investigate it as a drug candidate and to obtain compounds with a better activity profile.
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey.
authors.forename: Elif
authors.initials: E
authors.lastname: Unluer
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey.
authors.forename: Halise Inci
authors.initials: HI
authors.lastname: Gul
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey.
authors.forename: Alkan
authors.initials: A
authors.lastname: Demirtas
authors.affiliation: b Division of Pharmacology , Meikai University School of Dentistry , Sakado , Saitama , Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.affiliation: c Division of Oral Biochemistry , Asahi University School of Dentistry , Mizuho City , Gifu , Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Umemura
authors.affiliation: d Neurofarba Department and Laboratorio Di Chimica Bioinorganica, Università Degli Studi Di Firenze , Sesto Fiorentino (Florence) , Italy , and.
authors.forename: Muhammet
authors.initials: M
authors.lastname: Tanc
authors.affiliation: e Department of Chemistry , Faculty of Science, Ataturk University , Erzurum , Turkey.
authors.forename: Cavit
authors.initials: C
authors.lastname: Kazaz
authors.affiliation: d Neurofarba Department and Laboratorio Di Chimica Bioinorganica, Università Degli Studi Di Firenze , Sesto Fiorentino (Florence) , Italy , and.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors* / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D015394:Molecular Structure; D011407:Propane / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; D013438:Sulfhydryl Compounds; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II; D011407:Propane
keywords: Carbonic anhydrase inhibition; PARP; cytotoxicity; thiol addition