Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities

Tuğrak, Mehtap; Yamalı, Cem; Sakagami, Hiroshi; Gül, Halise İnci

doi:10.3109/14756366.2015.1070263

Cited by 49 publications

(31 citation statements)

References 31 publications

(32 reference statements)

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“…Chalcone derivatives (1, 2, 3) were synthesized as described in literatures 2,8,10,21 . An aqueous solution of sodium hydroxide (10% w/v, 10 ml) was added to a solution of the appropriate aryl aldehyde (0.02 mol) and 4-hydroxyacetophenone (0.02 mol) in ethanol (6 ml).…”

Section: Methodsmentioning

confidence: 99%

“…The cytotoxicity of the compounds were assayed toward human oral squamous cell carcinoma cell lines (HSC-2, HSC-3, HSC-4) (purchased from Riken Cell Bank, Tsukuba, Japan) and human normal oral cells (HGF, HPLF) (established from the first premolar tooth extracted from the lower jaw of a 12-year-old girl) as described with some minor modifications 14,16,21,22,34 . All cells were cultured in DMEM (Sigma-Aldrich Inc., St. Louis, MO) supplemented with 10% fetal bovine serum (FBS) (SigmaAldrich).…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

“…Mannich bases are generally formed by the reaction between a compound containing a reactive hydrogen atom, formaldehyde, and mostly secondary amine 2,17 . The chemistry of Mannich bases has been the subject of wide and increasing interest, due to their biological activities such as analgesic, antimalarial, anticonvulsant, antipsychotic, cytotoxic, antiinflammatory, and antimicrobial activities [3][4][5]8,9,[17][18][19][20][21][22] . In addition, the Mannich bases of several bioactive molecules such as Taxol (anticancer agent), SCH48461 (anticholesterol agent), Tramadol (analgesic), Osnervan (antiparkinson), and Moban (neuroleptic) were prepared and they showed increased bioactivities comparing to the parent compounds 23 .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Yamalı

Gül

Sakagami

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Phenolic bis Mannich bases having the chemical structure of 1-[3,5-bis-aminomethyl-4-hydroxyphenyl]-3-(4-halogenophenyl)-2-propen-1-ones (1a-c, 2a-c, 3a-c) were synthesized (Numbers 1, 2, and 3 represent fluorine, chlorine, and bromine bearing compounds, respectively, while a, b, and c letters represent the compounds having piperidine, morpholine, and N-methyl piperazine) and their cytotoxic and carbonic anhydrase (CA, EC 4.2.1.1) enzyme inhibitory effects were evaluated. Lead compounds should possess both marked cytotoxic potencies and selective toxicity for tumors. To reflect this potency, PSE values of the compounds were calculated. According to PSE values, the compounds 2b and 3b may serve as lead molecules for further anticancer drug candidate developments. Although the compounds showed a low inhibition potency toward hCA I (25-43%) and hCA II (6-25%) isoforms at 10 mM concentration of inhibitor, the compounds were more selective (1.5-5.2 times) toward hCA I isoenzyme. It seems that the compounds need molecular modifications for the development of better CA inhibitors.

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Section: Methodsmentioning

confidence: 99%

Section: Cytotoxicity Assaymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Yamalı

Gül

Sakagami

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The cytotoxicity of the compounds were assayed towards human oral squamous cell carcinoma cell lines (Ca9-22, HSC-2, HSC-3, HSC-4) and human normal oral cells (HGF, HPLF, HPC) as described with some minor modifications [32][33][34][35][36][37] . All cells were cultured in DMEM supplemented with 10% fetalbovine serum (FBS).…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Küçükoğlu

Oral

Aydin

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of polymethoxylated-pyrazoline benzene sulfonamides were synthesized, investigated for their cytotoxic activities on tumor and non-tumor cell lines and inhibitory effects on carbonic anhydrase isoenzymes (hCA I and hCA II). Although tumor selectivity (TS) of the compounds were less than the reference compounds 5-Fluorouracil and Melphalan, trimethoxy derivatives 4, 5, and 6 were more selective than dimethoxy derivatives 2 and 3 as judged by the cytotoxicity assay with the cells both types originated from the gingival tissue. The compound 6 (4-[3-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl] benzene sulfonamide) showed the highest TS values and can be considered as a lead molecule of the series for further investigations. All compounds synthesized showed superior CA inhibitory activity than the reference compound acetazolamide on hCA I, and II isoenzymes, with inhibition constants in the range of 26.5-55.5 nM against hCA I and of 18.9-28.8 nM against hCA II, respectively.

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“…The compounds were assayed toward human oral squamous cell carcinoma cell lines (HSC-2, HSC-3, HSC-4), human promyelocytic leukemic cell line (HL-60) and human oral normal mesenchymal cells (gingival fibroblast (HGF), pulp cells (HPC) and periodontal ligament fibroblast (HPLF)) based on a literature procedure with some minor modifications [26][27][28] . In brief, cells were cultured in DMEM supplemented with 10% fetal bovine serum (FBS) except the HL-60 cells that were cultured in RPMI 1640 medium supplemented with 10% FBS.…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones

Unluer

Gül

Demirtaş

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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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.

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Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities

Cited by 49 publications

References 31 publications

Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones

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