- Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives
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Current study based on the synthesis of new thiazole derivatives via “one pot” multicomponent reaction, evaluation of their in vitro α-glucosidase inhibitory activities, and in silico studies. All synthetic compounds were fully characterized by 1H NMR, 13C NMR and EIMS. CHN analysis was also performed. These newly synthesized compounds showed activities in the range of IC50?=?9.06?±?0.10–82.50?±?1.70?μM as compared to standard acarbose (IC50?=?38.25?±?0.12?μM). It is worth mentioning that most of the compounds such as 1 (IC50?=?23.60?±?0.39?μM), 2 (IC50?=?22.70?±?0.60?μM), 3 (IC50?=?22.40?±?0.32?μM), 4 (IC50?=?26.5?±?0.40?μM), 6 (IC50?=?34.60?±?0.60?μM), 7 (IC50?=?26.20?±?0.43?μM), 8 (IC50?=?14.06?±?0.18?μM), 9 (IC50?=?17.60?±?0.28?μM), 10 (IC50?=?27.16?±?0.41?μM), 11 (IC50?=?19.16?±?0.19?μM), 12 (IC50?=?9.06?±?0.10?μM), 13 (IC50?=?12.80?±?0.21?μM), 14 (IC50?=?11.94?±?0.18?μM), 15 (IC50?=?16.90?±?0.20?μM), 16 (IC50?=?12.60?±?0.14?μM), 17 (IC50?=?16.30?±?0.29?μM), and 18 (IC50?=?32.60?±?0.61?μM) exhibited potent inhibitory potential. Molecular docking study was performed in order to understand the molecular interactions between the molecule and enzyme. Newly identified α-glucosidase inhibitors except few were found to be completely non-toxic.
- Khan, Khalid Mohammed,Qurban, Saira,Salar, Uzma,Taha, Muhammad,Hussain, Shafqat,Perveen, Shahnaz,Hameed, Abdul,Ismail, Nor Hadiani,Riaz, Muhammad,Wadood, Abdul
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- Synthesis and biological evaluation of N-aryl-2-phenyl-hydrazinecarbothioamides: Experimental and theoretical analysis on tyrosinase inhibition and interaction with HSA
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A series of N-aryl-2-phenyl-hydrazinecarbothioamides have been investigated as possible inhibitors of tyrosinase, an enzyme involved in the development of melanomas. The hydrazinecarbothioamides 1–6 were synthesized from the reaction between phenylhydrazine and isothiocyanates, for which three different methods have been employed, namely stirring at room temperature, by microwave irradiation or by mechanochemical grinding. Quantitative yields were obtained for the later technique. Compound 4 showed the best value for tyrosinase inhibition (IC50 = 22.6 μM), which occurs through an uncompetitive mechanism. Molecular docking results suggested that 4 can interact via T-stacking with the substrate L-DOPA and via hydrogen bonding and hydrophobic forces with the amino acid residues Ala-79, His-243, Val-247, Phe-263, Val-282, and Glu-321. The interaction between human serum albumin (HSA) and compound 4 occurs through a ground state association and does not perturb the secondary structure of the albumin as well as the microenvironment around Tyr and Trp residues. The binding is spontaneous, moderate and occurs mainly in the Sudlow's site I. Molecular docking results suggested hydrogen bonding, hydrophobic and electrostatic interactions as the main binding forces between the compound 4 and the amino acid residues Lys-198, Trp-214, Glu-449, Leu-452, and Leu-480.
- Sousa-Pereira, Danilo,Chaves, Otávio Augusto,dos Reis, Camilla Moretto,de Oliveira, Márcia C.C.,Sant'Anna, Carlos Maurício R.,Netto-Ferreira, José Carlos,Echevarria, Aurea
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- UV-visible and 1H-15N NMR spectroscopic studies of colorimetric thiosemicarbazide anion sensors
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Four model thiosemicarbazide anion chemosensors containing three N-H bonds, substituted with phenyl and/or 4-nitrophenyl units, were synthesised and studied for their anion binding abilities with hydroxide, fluoride, acetate, dihydrogen phosphate and chlo
- Farrugia, Kristina N.,Makuc, Damjan,Podborska, Agnieszka,Szacilowski, Konrad,Plavec, Janez,Magri, David C.
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p. 1662 - 1672
(2015/03/05)
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- Drug resistance modulation in staphylococcus aureus, a new biological activity for mesoionic hydrochloride compounds
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Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1, 3,4- thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1, 3,4- thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenylthiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, 1H-NMR, 13C-NMR and elemental analysis. These compounds were analyzed for their influence on the effectiveness of norfloxacin, tetracycline, and erythromycin (standard antibiotics) against resistant strains of Staphylococcus aureus. MC-1 and MC-2, at sub-inhibitory concentrations of 16 μg/mL, favourably modulated the antibiotic activity of tetracycline by 16- and 32-fold, respectively (MIC), and that of erythromycin by 4-fold.
- De Oliveira, Cledualdo Soares,Falcao-Silva, Vivyanne Dos Santos,Siqueira-Junior, Jose Pinto,Harding, David Peter,Lira, Bruno Freitas,Lorenzo, Jorge Goncalo Fernandes,Barbosa-Filho, Jose Maria,De Athayde-Filho, Petrnio Filgueiras
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experimental part
p. 2023 - 2031
(2011/05/11)
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- Synthesis, phytotoxic, cytotoxic, acetylcholinesterase and butrylcholinesterase activities of N,N-diaryl unsymmetrically substituted thioureas
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Fourteen N,N-diaryl unsymmetrically substituted thioureas were synthesised and their cytotoxic (in vitro), phytotoxic (in vitro), acetylcholinesterase and butrylcholinesterase activities were determined. Thiourea 16 exhibited high, and 1 and 3 showed significant phytotoxic activity. Thioureas 1, 3, 4, 6 and 10 showed significant activity and 2, 6 and 7 indicated moderate cytotoxic activities. Compound 12 exhibited butrylcholinesterase activity higher than a standard reference.
- Begum, Saeedan,Choudhary, M. Iqbal,Khan, Khalid M.
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experimental part
p. 1719 - 1730
(2010/05/18)
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- Synthesis of mesoionic 4-(para-substituted phenyl-5-2,4-dichlorophenyl)-1, 3-4-thiadiazolium-2-aminides by direct cyclization via acylation of thiosemicarbazides
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The synthesis of ten novel mesoionic 4-[para-substituted (H, CH 3, OCH3, NO2, Cl, Br, OH, t-C4H 9, C6H5, C4H9) phenyl-5-2,4-dichlorophenyl]-1,3-4-thiadiazolium-2-aminides, as hydrochlorides, are described. The synthesis strategy utilized the corresponding para-substituted isothiocyanates as starting materials to obtain the thiosemicarbazides through reaction with phenylhydrazine (61-98%), which were then submitted to acylation with 2,4-dichloro benzoyl chloride and direct cyclization to generate the desired substituted mesoionic compounds in good yields (ca. 80%). Copyright Taylor & Francis Group, LLC.
- Britto, Marcelo Moreira,Almeida, Tania Mara Grigolli,Leitao, Andrei,Donnici, Claudio Luis,Lopes, Miriam Tereza Paz,Montanari, Carlos Alberto
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p. 3359 - 3369
(2007/10/03)
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- Synthesis and multinuclear NMR investigation of some mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imines
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Six new derivatives of mesoionic 3-phenyl-5-imino-1,2,3,4-oxatriazole imine have been obtained and investigated by 1H, 13C, 14N, 15N and 17O NMR techniques. The 15N and 17O NMR s
- Ja?wiński, Jaros?aw,Staszewska-Krajewska, Olga
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- INVESTIGATIONS IN THE SERIES OF DITHIOCARBAMIC ACID DERIVATIVES. IX. ARYLHYDRAZINOTHIOCARBONYLATION OF COMPOUNDS CONTAINING AN ACTIVE HYDROGEN ATOM
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The reaction of methyl phenyldithiocarbazate with ethyl cyanoacetate, cyanoacetamide, acetylacetone, and malonic ester leads to the formation of 1,4,5-trisubstituted pyrazoline-3-thiones.The reaction of methyl phenyldithiocarbazate with arylamines and arylhydrazines gave the respective derivatives of thiosemicarbazide and thiocarbohydrazide.
- Bazavova, I. M.,Dubenko, R. G.,Pel'kis, P. S.
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p. 189 - 193
(2007/10/02)
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