Synthesis, anti-Trypanosoma cruzi activity and quantitative structure relationships of some fluorinated thiosemicarbazones

Santos, Jonas da Silva; Melos, Jorge Luiz R. de; Lima, Gerson Silva de; Lyra, Jade Crespo; Guedes, Guilherme P.; Rodrigues-Santos, Cláudio Eduardo; Echevarrı́a, Aurea

doi:10.1016/j.jfluchem.2017.01.013

Cited by 11 publications

(2 citation statements)

References 29 publications

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“…The compounds 2-(2-arylidenehydrazinyl)-4-(4-methoxyphenyl)thiazoles (3a-o) were prepared by heating an equimolar mixture of respective thiosemicarbazones [24][25][26][27][28][29][30][31][32][33] and 2-bromo-4-methoxy acetophenone in absolute ethanol as shown in Scheme 1. [34 -36] The cyclized products were achieved in moderate to good yield (67-79 %).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Haroon

Mehmood

Akhtar

et al. 2022

Chemistry & Biodiversity

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Thiazole has been a key scaffold in antidiabetic drugs. In quest of new and more effective drugs a simple, efficient, high yielding (67-79 %) and convenient synthesis of arylidenehydrazinyl-4-methoxyphenyl)thiazoles is accomplished over two steps. The synthesis involved the condensation of aryl substituted thiosemicarbazones and 2-bromo-4-methoxyacetophenone in absolute ethanol. The structures of the resulting thiazoles are in accord with their UV/VIS, FT-IR, 1 H-, 13 C-NMR and HRMS data. All compounds were evaluated for alpha(α)-amylase inhibition potential, antiglycation, antioxidant abilities and biocompatibility. The compounds library identified 2-(2-(3,4-dichlorobenzylidene)hydrazinyl)-4-(4-methoxyphenyl)thiazole as a lead molecule against α-amylase inhibition with an IC 50 of 5.75 � 0.02 μM. α-Amylase inhibition is also supported by molecular docking studies against α-amylase. All the obtained thiazoles also showed promising antiglycation activity with 4-(4methoxyphenyl)-2-{2-[2-(trifluoromethyl)benzylidene]hydrazinyl}thiazole exhibiting the best inhibition (IC 50 = 0.383 � 0.001 mg/mL) compared to control. The tested compounds are also biocompatible at the concentration used i. e., 10 μM.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Haroon

Mehmood

Akhtar

et al. 2022

Chemistry & Biodiversity

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“…The use of thiosemicarbazones are also utilized as catalyst [35,36] and possess significant mushroom tyrosinase inhibiton activities [37]. A variety of thiosemicarbazone [38][39][40] have been involved in the treatment of trypanosomiasis caused by Trypanosoma cruzi parasite.…”

Section: Biological Importance Of Semicarbazones and Thiosemicarbazonesmentioning

confidence: 99%

Biological Applications of Co(II) and Ni(II) Complexes of Semicarbazones and Thiosemicarbazones

Jain¹,

Kumar²,

Chandra³

2018

Asian J. Chem.

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Ni(II) and Cu(II) complexes of bidentate thiosemicarbazone ligand: Synthesis, structural, theoretical, biological studies and molecular modeling

Jain¹,

Sharma²,

Kumar³

et al. 2020

Applied Organom Chemis

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The conventional condensation and refluxing process was employed to synthesize Ni(II) and Cu(II) complexes of Methylcarbamatethiosemicarbazone ligand. Reactions were carried out at the pH of 7. The molar ratio of the ligand and metal salt was 2:1. The structures of the synthesized metal complexes were suggested by different analytical techniques such as magnetic susceptibility, molar conductance, IR, EPR and UV spectroscopy. Experimental studies confirmed the octahedral geometry for all the complexes. The geometry of the ligand and complexes were also confirmed by theoretical studies. The complexes were investigated for biological action against pathogenic fungi (C. krusei, C. albican) and bacteria (S. aureus, E. coli). The antimicrobial results confirmed superior inhibition potential of the metal complexes as compared with the parent ligand. The enhanced antimicrobial activities might be due to the chelation. Molecular‐docking assays confirmed the strong interaction of ligand with target antimicrobial protein DNA gyrase‐B.

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Synthesis, anti-Trypanosoma cruzi activity and quantitative structure relationships of some fluorinated thiosemicarbazones

Cited by 11 publications

References 29 publications

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Biological Applications of Co(II) and Ni(II) Complexes of Semicarbazones and Thiosemicarbazones

Ni(II) and Cu(II) complexes of bidentate thiosemicarbazone ligand: Synthesis, structural, theoretical, biological studies and molecular modeling

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