Synthesis of 1-aroyl-3,5-dimethyl-1H-pyrazoles as Anti-HCV and Anticancer Agents

Aydin, Sevil; Kaushik‐Basu, Neerja; Özbaş-Turan, Suna; Akbuğa, Jülide; Tiber, Pınar Mega; Orun, Oya; Gurukumar, K. R.; Basu, Amartya; Küçükgüzel, Ş. Güniz

doi:10.2174/15701808113109990069

Cited by 20 publications

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“…Their structures were further confirmed from their 1 H-NMR and 13 C NMR spectral data (Tables 2 and 3). …”

mentioning

confidence: 73%

“…The 1 H-NMR exhibited besides the aromatic protons at 6.01-7.41 ppm, Table 2). The structures were further confirmed from their 13 C NMR spectral data ( Table 3). The new 1-thiocarbamoyl and carbamoyl derivatives 4 and 5 were prepared by either treating the corresponding pyrazole with the appropriate isothiocyanate or isocyanate respectively or by condensing the corresponding chalcone with the proper substituted semicarbazide 15 or thiosemicabazide 26 (Table 1).…”

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confidence: 80%

“…The infrared (IR) spectra were recorded on Shimadzu FT-IR 8400S infrared spectrophotometer (Tokyo, Japan) using the KBr pellet technique. 1 H and 13 C NMR spectra were recorded on a Bruker DPX-400 FT NMR spectrometer (Bruker BioSpin AG, Fällanden, Switzerland) using tetramethylsilane as the internal standard and a mixture of CDCl 3 and DMSO-d 6 as a solvent (Chemical shifts in , ppm). Splitting patterns were designated as follows: s: singlet; d: doublet; m: multiplet.…”

Section: Chemistrymentioning

confidence: 99%

“…The discovery of the naturally occurring C-glycoside antibiotic pyrazofurin; 4-hydroxy-3-b-Dribofuranosyl-1H-pyrazole-5-carboxamide 6 , however, has provided a basis for a rational design of new pyrazoles as potential antimicrobial 7,8 , antiviral 9,10 and anticancer agents 8,[11][12][13] . It has also been reported that isoquinoline-1-carboxaldehyde thiosemicarbazone and its several congeners which possess the N-N-S or O-N-S tridentate ligand system, exhibit substantial antineoplastic activity 14,15 .…”

Section: Introductionmentioning

confidence: 99%

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1-Substituted carbamoyl and thiocarbamoyl-4,5-dihydro-1H-pyrazoles as possible cytotoxic and antimicrobial agents

Khan

Faidallah

2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Two series of 1-substituted carbamoyl and thiocarbomoyl derivatives were prepared by either treating the corresponding pyrazole with the appropriate isocyanate and isothiocyanate respectively, or alternatively by condensing the appropriate diketone with the proper substituted semicarbazide or thiosemicarbazide. The structures of the prepared compounds were fully determined by analytical and spectral methods. Preliminary biological screening of the prepared compounds revealed significant antibacterial and cytotoxic activities for some compounds. Compounds 4a 2 and 4a 3 were found to be the most active against the human colon carcinoma HT29 (11.8 and 7.5 mg/mL, respectively) and human breast cancer MCF 7 (3.4 and 2.6 mg/mL, respectively) cell lines. The structure-activity relationship (SAR) and in silico drug relevant properties (HBD, HBA, tPSA, cLog P, molecular weight, % ABS, drug-likeness and drug score) further confirmed that the compounds are potential lead compounds for future drug discovery study.

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“…Their structures were further confirmed from their 1 H-NMR and 13 C NMR spectral data (Tables 2 and 3). …”

mentioning

confidence: 73%

mentioning

confidence: 80%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1-Substituted carbamoyl and thiocarbamoyl-4,5-dihydro-1H-pyrazoles as possible cytotoxic and antimicrobial agents

Khan

Faidallah

2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In the present study, indapamide which has indole ring and sulfonamide group was chosen as the starting material and some related 4-thiazolidinone derivatives were synthesized. 4-Chloro-3-({[3-(substituted)-4-oxo-1,3-thiazolidine-2-ylidene] amino}sulfonyl)-N-(2-methyl-2,3-dihydro-1H-indole-1-yl)benzamides (21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31) were synthesized by the addition of ethyl a-bromoacetate and anhydrous sodium acetate in dry ethanol to 4-chloro-3-({[(substitutedamino)carbono-thioyl]amino}sulfonyl)-N-(2-methyl-2,3-dihydro-1H-indole-1-yl)benzamides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), which were synthesized by the reaction of alkyl/aryl isothiocyanates with indapamide. The structures of the isolated products were determined by the spectral methods and evaluated anticancer activity for the selected compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pro-apoptotic indapamide derivatives as anticancer agents

Yılmaz

Turan

Akbuğa

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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benzamide 12 demonstrated the highest proapoptotic activity among all synthesized compounds on melanoma cell lines MDA-MB-435 with 3.7% growth inhibition at the concentration of 10 mM. Compound 12 (SGK 266) was evaluated in vitro using the MTT colorimetric method against melanoma cancer cell line MDA-MB435 growth inhibition for different doses and exhibited anticancer activity with IC 50 values of 85-95 mM against melanoma cancer cell line MDA-MB435. In addition, this compound was investigated as inhibitors of four physiologically relevant human carbonic anhydrase isoforms, hCA I, II, IX and XII. The compund inhibited these enzymes with IC 50 values ranging between 0.72 and 1.60 mM.

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Synthesis of Tolmetin Hydrazide–Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Cells

Küçükgüzel

Koç

Çıkla-Süzgün

et al. 2015

Archiv der Pharmazie

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Tolmetin hydrazide and a novel series of tolmetin hydrazide-hydrazones 4a-l were synthesized in this study. The structures of the new compounds were determined by spectral (FT-IR, (1)H NMR) methods. N'-[(2,6-Dichlorophenyl)methylidene]-2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetohydrazide (4g) was evaluated in vitro using the MTT colorimetric method against the colon cancer cell lines HCT-116 (ATCC, CCL-247) and HT-29 (ATCC, HTB-38) to determine growth inhibition and cell viability at different doses. Compound 4g exhibited anti-cancer activity with an IC50 value of 76 μM against colon cancer line HT-29 (ATCC, HTB-38) and did not display cytotoxicity toward control NIH3T3 mouse embryonic fibroblast cells compared to tolmetin. In addition, this compound was evaluated for caspase-3, caspase-8, caspase-9, and annexin-V activation in the apoptotic pathway, which plays a key role in the treatment of cancer. We demonstrated that the anti-cancer activity of this compound was due to the activation of caspase-8 and caspase-9 involved in the apoptotic pathway. In addition, in this study, we investigated the catalytical effect of COX on the HT-29 cancer line, the apoptotic mechanism, and the moleculer binding of tolmetin and compound 4g on the COX enzyme active site.

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Synthesis of 1-aroyl-3,5-dimethyl-1H-pyrazoles as Anti-HCV and Anticancer Agents

Cited by 20 publications

References 0 publications

1-Substituted carbamoyl and thiocarbamoyl-4,5-dihydro-1H-pyrazoles as possible cytotoxic and antimicrobial agents

1-Substituted carbamoyl and thiocarbamoyl-4,5-dihydro-1H-pyrazoles as possible cytotoxic and antimicrobial agents

Synthesis of pro-apoptotic indapamide derivatives as anticancer agents

Synthesis of Tolmetin Hydrazide–Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Cells

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