Design, Synthesis and Pharmacological Evaluation of New Nonsteroidal Antiinflammatory 1,3,4-Thiadiazole Derivatives

Varandas, L. S.; Fraga, Carlos A.M.; Miranda, A. L.P.; Barreiro, Eliezer J.

doi:10.2174/1570180053398235

Cited by 19 publications

(5 citation statements)

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“…Numerous compounds of biological interest both natural and man‐made have the Schiff base nucleus. These compounds show potent antioxidant, antibacterial, antiviral, analgesic, antiplatelet, antimicrobial, antimalarial and anticancer activities as revealed by literature studies . The azomethine linkage in these compounds is of prime importance as it is instrumental in these compounds exhibiting antitumor activity .…”

Section: Introductionmentioning

confidence: 99%

4‐Hydroxy‐benzoic acid (4‐diethylamino‐2‐hydroxy‐benzylidene)hydrazide: DFT, antioxidant, spectroscopic and molecular docking studies with BSA

2015

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The Schiff base 4-hydroxy-benzoic acid (4-diethylamino-2-hydroxy-benzylidene) hydrazide (SL) was synthesized and characterized. Its antioxidant activity was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging action. Being a potent antioxidant its binding ability to the transport protein bovine serum albumin (BSA) was studied using fluorescence quenching and circular dichroism (CD) studies. The binding distance has been calculated by fluorescence resonance energy transfer (FRET) to be 1.85 Å and the Stern-Volmer quenching constant has been calculated to be (3.23 ± 0.45) × 10(5) M(-1). Quantum chemical analysis was carried out for the Schiff base using DFT with B3LYP and 6-311G** and related to the experimentally obtained results. For a deeper understanding of the mechanism of the interaction, the experimental data were complemented by protein-Schiff base docking calculations using Argus Lab.

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Section: Introductionmentioning

confidence: 99%

4‐Hydroxy‐benzoic acid (4‐diethylamino‐2‐hydroxy‐benzylidene)hydrazide: DFT, antioxidant, spectroscopic and molecular docking studies with BSA

2015

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“…The triazole-and thiadiazole-based compounds have been reported as antimicrobials , antivirals [22][23][24], antitumors [6,10,[25][26][27][28][29][30][31], anticonvulsants [11,32,33] antidepressants [34][35][36], analgesic [8,[37][38][39][40][41] and anti-inflammatory [8,9,37,38,[42][43][44][45][46] agents. An excellent strategy for the synthesis of these azoles is the dehydrocyclization of 1,4-disubstituted thiosemicarbazides.…”

Section: Introductionmentioning

confidence: 99%

Does dehydrocyclization of 4-benzoylthiosemicarbazides in acetic acid lead to s-triazoles or thiadiazoles?

et al. 2012

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Ever since the recognition of strong pharmaceutical activities of triazoles and thiadiazoles, these scaffolds have been the subject of vigorous studies. One of the best strategies for synthesis of these azoles is dehydrocyclization of 1,4-disubstituted thiosemicarbazides, which leads to s-triazoles in alkaline media, whereas in strong acidic media 1,3,4-thiadiazoles are formed. However, the literature is riddled with contradictory communications regarding the nature of the products of such reactions under mild acidic conditions. As these compounds are not amenable to X-ray analysis, we have resorted to NMR and theoretical modelling to resolve this discrepancy. In this article, we present arguments indicating that dehydrocyclization of 4-benzoylthiosemicarbazides in glacial acetic acid leads to thiadiazole derivatives. These structural findings are augmented by studies of bioactivity of a few members of the studied class of compounds.

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“…The biological activity of the compounds is mainly dependent on their molecular structures (Salimon et al ., 2010 ). A vast number of 1,3,4-thiadiazoles have been reported as potential pharmacologically active compounds with antimicrobial (Patil and Biradar, 2001 ; Zamani et al ., 2004 ; Sharma et al ., 2006 ), antiviral (Pandey et al ., 2004 ), antitubercular (Oruc et al ., 2004 ; Desai et al ., 1984 ), anticonvulsant (Shrivastava et al ., 1999 ; Kumar et al ., 2003 ; Gupta et al ., 2008 ; Stillings et al ., 1986 ; Jatav et al ., 2008 ), CNS depressant (Jatav et al ., 2008 ), hypoglycaemic (Hanna et al ., 1995 ; Pattan et al ., 2009 ), anti-inflammatory (Sharma et al ., 2008 ; Varandas et al ., 2005 ) and anticancer (Noolvi et al ., 2011 ; Kumar et al ., 2010 ) properties. At the same time, the 1,3,4-thiadiazole fragment appears in a number of clinically used drugs such as acetazolamide; methazolamide; butazolamide (diuretic); sulfamethiazole (antibacterial); cefazolin, cefazedone (antibiotic); atibeprone (anti-depressant); glybuthiazole, glybuzole (antidiabetic); and tebuthiuron (insecticide) (Wilson and Gisvold, 1991 ; Abrahum, 2003 ; Supran et al ., 2003 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells

2013

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A series of imines 5-amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamide derivatives were synthesized from various aromatic aldehydes and substituted with benzoyl acetazolamides under different reaction conditions and were evaluated for their antioxidant and free radical scavenging, antimitotic activity by Allium cepa meristem root model and cytotoxicity activity against HEK 293 (human epidermal kidney cell line), BT474 (breast cancer cell line) and NCI-H226 (lung cancer cell line) by MTT assay. Some of the synthesized compounds showed moderately potent cytotoxicity compared to indisulam. Graphical abstractA series of imines 5-amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamide derivatives (9a–j); 5-amino-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (4a–g); 5-(4-acetamido phenyl sulphonamido)-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (6a–g); and 5-(4-amino phenyl sulphonamido)-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (7a–g) were synthesized from acetazolamide and were investigated for the in vitro anticancer by MTT assay, free radical scavenging and antimitotic activity by Allium cepa root meristem model. Experimental observations indicate that synthesized compounds were moderately potent anticancer agents.

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Design, Synthesis and Pharmacological Evaluation of New Nonsteroidal Antiinflammatory 1,3,4-Thiadiazole Derivatives

Cited by 19 publications

References 0 publications

4‐Hydroxy‐benzoic acid (4‐diethylamino‐2‐hydroxy‐benzylidene)hydrazide: DFT, antioxidant, spectroscopic and molecular docking studies with BSA

4‐Hydroxy‐benzoic acid (4‐diethylamino‐2‐hydroxy‐benzylidene)hydrazide: DFT, antioxidant, spectroscopic and molecular docking studies with BSA

Does dehydrocyclization of 4-benzoylthiosemicarbazides in acetic acid lead to s-triazoles or thiadiazoles?

Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells

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