Synthesis, experimental, theoretical characterization and biological activities of 4-ethyl-5-(2-hydroxyphenyl)-2H-1,2,4-triazole-3(4H)-thione

Koparır, Metin; Örek, Cahit; Koparır, Pelin; Sarac, Kamiran

doi:10.1016/j.saa.2012.12.052

Cited by 41 publications

(17 citation statements)

References 66 publications

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“…The C=O stretching vibrations are viewed in the part of 1780-1700 cm-1 (23). In this study, the bands appeared 1736 cm-1 (1) and 1739 (2) experimentally are belong to C=O group and the corresponding calculated wave numbers are 1767 cm-1 (1) and 1766 (2). The reported value of stretching mode of COC in the ring (C4-O7) was 1216 cm-1 for 3-(bromoacetyl) coumarin (23).…”

Section: Co Vibrationsmentioning

confidence: 57%

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Molecular structure, vibration properties and quantum chemical calculations of 4-(chloromethyl)-7-methoxycoumarin and 4-(chloromethyl)-7-methyl-coumarin

Akman

Saraç

2016

Natural Science and Discovery

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Section: Co Vibrationsmentioning

confidence: 57%

“…The substitution of coumarins represents one of the most biologically active classes of compounds, possessing a wide spectrum of activities, including analgesic, antimicrobial, anticancer, anti-viral, anti-inflammatory (2). Coumarins are used as drug.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure, vibration properties and quantum chemical calculations of 4-(chloromethyl)-7-methoxycoumarin and 4-(chloromethyl)-7-methyl-coumarin

Akman

Saraç

2016

Natural Science and Discovery

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“…The RMSE value is calculated as 0.32 Å. The calculated dihedral angles between the 1,2,4 triazole ring and the C31-C36 and C51-C56 rings of the molecular structure that is formed after the optimization of compound (3) [27][28][29]. C≡N stretching vibration in the phthalonitrile ring is seen expressly at 2200-2300 cm -1 as a sharp peak.…”

Section: Theoretical and Experimental Molecular Structure Parametersmentioning

confidence: 99%

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Çoruh

Ustabaş

Akçay

et al. 2016

Maced. J. Chem. Chem. Eng.

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In this study, 4-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile was synthesized and its molecular structure was characterized by means of FT-IR and X-ray diffraction methods. The crystal is monoclinic and belongs to the P21/n space group. There are three weak intermolecular C-H…N type hydrogen bonds in the molecular structure. The geometrical parameters, vibration frequencies, HOMO-LUMO energies, and molecular electrostatic potential (MEP) map of the compound (3) in ground state were calculated by using density functional theory (DFT/B3LYP) with the 6-311G(d) basis set. Calculated geometrical parameters were compared with X-ray diffraction geometric parameters. On the other hand, theoretical and experimental FT-IR results were also compared.Keywords: crystal structure; 1,2,4-triazole; DFT calculations; molecular electrostatic potential; frontier orbitals ЕКСПЕРИМЕНТАЛНИ И ТЕОРЕТСКИ ИСПИТУВАЊА НА 4-[(4-МЕТИЛ-5-ФЕНИЛ-4H1,2,4-ТРИАЗОЛ-3-ИЛ)СУЛФАНИЛ]БЕНЗЕН-1,2-ДИКАРБОНИТРИЛВо ова истражување беше синтетизиран 4-[(4-метил-5-фенил-4Н1,2,4-триазол-3-ил)сул-фанил]бензен-1,2-дикарбонитрил, а неговата структура беше карактеризирана со помош на FT-IR и рендгенска дифракција. Кристалот е моноклиничен и припаѓа на просторната група P21/n. Во молекулската структура постојат три слаби интермолекулски водородни врски од типот на C-H…N. Геометриските параметри, вибрациските фреквенции, енергиите на HOMO-LUMO и мапата на молекулскиот електростатички потенцијал (MEP) на соединението (3) во основна состојба беа пресметани со теоријата на функционалот на густината (DFT/B3LYP) и основен сет 6-311G(d). Пресметаните геометриски параметри беа споредени со геометриските параметри добиени со рендгенската дифракција. Исто така беа споредени и теоретските и експерименталните резултати добиени со FT-IR.Клучни зборови: кристална структура; 1,2,4-триазол; DFT пресметки; молекулски електростатички потенцијал; гранични орбитали U. Çoruh, R. Ustabaş, H. T. Akçay, E. Menteşe, E. M. V. Lopez Maced.

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“…The indole ring of these compounds is the reactive centre dealing with oxidants due to its high resonance stability and low activation energy barrier towards free radical reactions 24,26 . In addition to these compounds, there are some studies that demonstrate the antioxidant effect of 1,2,4-triazoles and 1,3,4-thiadiazoles [27][28][29] . The triazole molecule is one of the most significant and well recognized heterocycles which is a common feature of a selection of natural products as well as pharmaceutical agents.…”

Section: Introductionmentioning

confidence: 99%

Novel indole-based melatonin analogues substituted with triazole, thiadiazole and carbothioamides: studies on their antioxidant, chemopreventive and cytotoxic activities

Shirinzadeh

İnce

Westwell

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Melatonin (MLT) is a well-known free-radical scavenger, involving in the prevention of cellular damage that can lead to cancer, ageing and a variety of neurodegenerative diseases. Research on MLT-related compounds has been required to optimise the maximum pharmaceutical activity with the lowest side effects. In our ongoing research, we have synthesized new indolebased MLT analogues as potential antioxidant agents by modifying the MLT molecule. In this study, we build on previous findings, through the synthesis, characterization and in vitro antioxidant profiling of a series of new indole-based MLT analogues which possess triazole, thiadiazole and carbothioamides on the third position on the indole ring. In vitro antioxidant activity was investigated by evaluating their reducing effect against oxidation of a redox sensitive fluorescent probe and their radical scavenging activity was assessed via the DPPH assay. In addition, in vitro cytotoxic effects of newly synthesized compounds were investigated in CHO-K1 cells using the MTT assay.

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Synthesis, experimental, theoretical characterization and biological activities of 4-ethyl-5-(2-hydroxyphenyl)-2H-1,2,4-triazole-3(4H)-thione

Cited by 41 publications

References 66 publications

Molecular structure, vibration properties and quantum chemical calculations of 4-(chloromethyl)-7-methoxycoumarin and 4-(chloromethyl)-7-methyl-coumarin

Molecular structure, vibration properties and quantum chemical calculations of 4-(chloromethyl)-7-methoxycoumarin and 4-(chloromethyl)-7-methyl-coumarin

Experimental and theoretical studies of 4-[(4-methyl-5-phenyl- 4H1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile

Novel indole-based melatonin analogues substituted with triazole, thiadiazole and carbothioamides: studies on their antioxidant, chemopreventive and cytotoxic activities

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