Synthesis and anticonvulsant activity of substituted thiourea derivatives

Celen, Ahmet Ozgur

doi:10.12991/201115430

Cited by 18 publications

(11 citation statements)

References 13 publications

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“…Thiourea derivatives are well known sulphur containing compounds acting as ligands in the field of coordination chemistry [1][2][3]. Such ligands are capable of affording complexes with metal ions; the resultant complexes have been reported to have imperative antimicrobial [4] and anticonvulsant [5] applications. Thiourea derivatives and their complexes have numerous catalytic applications in asymmetric organocatalysis [6][7][8], have been used as cocatalysts in Pauson-Khand reactions [1], Pd-catalyzed reactions [1,9], Heck and Suzuki coupling reactions, and so forth [2,9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and DFT Calculations of 1,3-Diisobutyl Thiourea

Altaf

Shahzad

Gul

et al. 2015

Journal of Chemistry

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1,3-Diisobutyl thiourea was synthesized and characterized by single crystal X-ray diffraction. It gives a monoclinic (α=γ= 90 andβ ≠90) structure with the space group P21/c. The unit cell dimensions area= 11.5131 (4) Å,b= 9.2355 (3) Å,c= 11.3093 (5) Å,α= 90°,β= 99.569° (2),γ= 90°,V= 1185.78 (8) Å3, andZ= 4. The crystal packing is stabilized by intermolecular (N–H⋯S) hydrogen bonding in the molecules. The optimized geometry and Mullikan's charges of the said molecule calculated with the help of DFT using B3LYP-6-311G model support the crystal structure.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and DFT Calculations of 1,3-Diisobutyl Thiourea

Altaf

Shahzad

Gul

et al. 2015

Journal of Chemistry

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“…A series of new thiourea and urea derivatives bearing 1,2,4-triazole rings were prepared according to Scheme 1. The thiourea derivatives 1a – e were previously synthesized and reported by Celen et al [23]. Compounds 2a – e were prepared by refluxing equimolar amounts of 4-(aminophenyl)acetic acid and various isocyanates in acetone.…”

Section: Resultsmentioning

confidence: 99%

“…In the IR spectra of compounds 3a – e , two C=S stretching bands due to the thiourea and thioxo groups were seen at 1320–1350 cm −1 and 1234–1294 cm −1 . In the 1 H-NMR spectrum, the carboxylic acid O-H peaks were observed as singlets at 11.98–12.58 ppm for compounds 1a – e [23], but were absent in the spectra of the 1,2,4-triazole derivatives 3a – e due to the ring closure. The N-H peaks of the triazole rings were seen at 11.70–12.30 ppm as singlets and the thiourea N-H peaks were observed at 7.83–9.79 ppm as two singlets.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Biological Activity of Substituted Urea and Thiourea Derivatives Containing 1,2,4-Triazole Moieties

Koçyığıt‐Kaymakcioğlu

Celen

Tabanca

et al. 2013

Molecules

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A series of novel thiourea and urea derivatives containing 1,2,4-triazole moieties were synthesized and evaluated for their antifungal and larvicidal activity. Triazole derivatives 3a-e and 4a-e were synthesized by reacting thiocarbohydrazide with thiourea and urea compounds 1a-e and 2a-e, respectively, in a 130-140 °C oil bath. The proposed structures of all the synthesized compounds were confirmed using elemental analysis, UV, IR, 1 H-NMR and mass spectroscopy. All compounds were evaluated for antifungal activity against plant pathogens, larvicidal and biting deterrent activity against the mosquito Aedes aegypti L. and in vitro cytotoxicity and anti-inflammatory activity against some human cell lines. Phomopis species were the most sensitive fungi to these compounds. Compounds 1b, 1c, 3a and 4e demonstrated selectively good activity against Phomopis obscurans and only 1b and 4e showed a similar level of activity against P. viticola. Compound 3d, with a LD 50 value of 67.9 ppm, followed by 1c (LD 50 = 118.8 ppm) and 3e (LD 50 = 165.6 ppm), showed the highest toxicity against OPEN ACCESSMolecules 2013, 18 3563Aedes aegypti larvae. Four of these compounds showed biting deterrent activity greater than solvent control, with the highest activity being seen for 1c, with a proportion not biting (PNB) value of 0.75, followed by 1e, 2b and 1a. No cytotoxicity was observed against the tested human cancer cell lines. No anti-inflammatory activity was observed against NF-B dependent transcription induced by phorbol myristate acetate (PMA) in human chondrosarcoma cells.

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“…The reaction of the compounds 1a-e and 2a-e with thiocarbohydrazide in oil bath afforded the corresponding 1,2,4-triazoles (3a-e and 4a-e). Physicochemical and spectroscopic characterization of all compounds have been previously described (15,16). The purities of the synthesized compounds were checked by reversed phase HPLC (Chromasil C 18 3.6x150 mm column using acetonitrile and water (70:30 v/v) as the eluent).…”

Section: Synthesis Of Test Compoundsmentioning

confidence: 99%

Some urea and thiourea derivatives bearing 1,2,4-triazole ring and their anti-acetylcholinesterase activities

Mohsen¹,

Koçyığıt‐Kaymakcioğlu

Celen³

et al. 2014

MUSBED

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ÖZET 1,2,4-Triazol halkası taşıyan bazı üre ve tiyoüre türevleri ve anti-asetilkolinesteraz aktiviteleri Amaç: Yirmi adet farklı tiyoüre ve üre türevleri sentezlenmiş ve asetilkolinesteraz enzimini (AChE) inhibe etme yetenekleri Ellman'ın modifiye spektrofotometrik yöntemi ile değerlendirilmiştir. Yöntem: Anti-asetilkolinesteraz aktivite tayini Ellman'ın modifiye edilmiş spektrofotometrik yöntemi kullanılarak yapılmıştır. Bu spektrofotometrik yöntem bir kromojenik reaktif olan 5,5-dithiobis-(2-nitrobenzoik asit) ile salınan tiyokolinin renkli bir ürün vermesi esasına dayanır. Bulgular: Sentezlenen bileşiklerin (1a-e, 2a-e, 3a-e ve 4a-4e) anti-asetilkolinesteraz aktivite tayini Ellman'ın modifiye edilmiş spektrofotometrik yöntemi kullanılarak yapılmıştır. Test edilen bileşikler arasında, (4-{[(4-triflorometilfenil)karbamoil]amino} fenil)asetik asit (1d), en yüksek aktivite gösteren bileşik olmuştur. Bileşik 1d'nin 0.1mM konsantrasyonda inhibisyon oranı %48.55 olarak hesaplanmıştır. Sonuç: Anti-asetilkolinesteraz aktivite tarama sonuçları incelediğinde, fenil halkasının 4. konumunda triflorometil grubu taşıyan bileşik 1d'nin kaydadeğer anti-asetilkolinesteraz aktivite gösterdiği tespit edilmiştir. Aktivite sonuçları incelendiğinde, fenil halkası üzerinde halojen taşıyan yapıların anti-asetilkolinesteraz aktiviteyi arttırıcı yönde katkı sağladığı gözlenmektedir. Anahtar sözcükler: Üre, tiyoüre, 1,2,4-triazol, anti-asetilkolinesteraz aktivite ABS TRACT Some urea and thiourea derivatives bearing 1,2,4-triazole ring and their antiacetylcholinesterase activities Objective: Twenty different urea and thiourea derivatives were synthesized and evaluated for their ability to inhibit acetylcholinesterase (AChE) using a modification of Ellman's spectrophotometric method. Methods: Anti-acetylcholinesterase activity was evaluated by using a modification of Ellman's spectrophotometric method. The spectrophotometric method is based on the reaction of released thiocholine to give a coloured product with a chromogenic reagent 5,5-dithio-bis-(2-nitrobenzoic acid). Results: The anti-acetylcholinesterase effects of the compounds (1a-e, 2a-e, 3a-e and 4a-4e) were determined by modified Ellman's spectrophotometric method. Among these compounds, (4-{[(4-trifluoromethylphenyl)carbamoyl]amino}phenyl)acetic acid (1d), was found as the most active compound. The inhibition percentages were calculated 48.55% at 0.1 mM concentrations for compound 1d. Conclusion: The anti-acetylcholinesterase activity screening indicated that among the tested compounds, 1d bearing 4-trifluoromethyl group on the phenyl ring, showed noteworthy anti-acetylcholinesterase activity. Based on the activity results, it appears that halogen atoms on the phenyl ring have made good contribution to the anti-acetylcholinesterase activity.

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Synthesis and anticonvulsant activity of substituted thiourea derivatives

Cited by 18 publications

References 13 publications

Synthesis, Crystal Structure, and DFT Calculations of 1,3-Diisobutyl Thiourea

Synthesis, Crystal Structure, and DFT Calculations of 1,3-Diisobutyl Thiourea

Synthesis and Biological Activity of Substituted Urea and Thiourea Derivatives Containing 1,2,4-Triazole Moieties

Some urea and thiourea derivatives bearing 1,2,4-triazole ring and their anti-acetylcholinesterase activities

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