- 1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles
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In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]
- Kalhor, Mehdi,Zarnegar, Zohre
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p. 519 - 540
(2021/12/03)
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- Sodium alginate: Biopolymeric catalyst for the synthesis of 2-amino-4-arylthiazole derivatives in aqueous medium
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Regarded as a naturally occurring macromolecule and without any post-modification, sodium alginate which possesses a granular form was found to be an efficient and recoverable bifunctional heterogeneous organocatalyst for the synthesis of 2-amino-4-arylthiazole derivatives was carried out by the reaction of substituted phenyl acetylene and thiourea in an eco-friendly condition in the presence of TBBDA (tetrabromobenzene-1,3-disulfonamide (tetrabromobenzene-1,3-disulfonamide). Mild reaction conditions, simple reaction procedure, easy purification, high yields of products, eco-friendly catalyst usage and convenient reusability are the highlighted points of this protocol.
- Gorji, Samareh,Ghorbani-Vaghei, Ramin,Alavinia, Sedigheh
-
-
- In vitro anticancer activity of thiazole based β-amino carbonyl derivatives against HCT116 and H1299 colon cancer cell lines; study of pharmacokinetics, physicochemical, medicinal properties and molecular docking analysis
-
The present study describes the synthesis and anticancer evaluation of certain substituted rac-(2S)-2-[(R)-[(4-substitutedphenyl){[4-(4-substitutedphenyl)-1,3-thiazol-2-yl]amino}methyl]cyclohexanone derivatives. The in vitro anticancer assay indicating su
- Gaidhane, Mahesh Krishanarao,Ghatole, Ajay Manohar,Hatzade, Kishor Manohar,Lanjewar, Kushal Radhesham
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p. 303 - 320
(2021/09/28)
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- Biological evaluation and synthesis of thiazole schiff base derivatives
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In this study, we report the synthesis of thiazole Schiff base derivatives (Z1-Z16) and their tyrosinase inhibitory activity, anti-oxidant activities. Mushroom tyrosinase inhibitory assay showed compound Z8 (IC50 = 2.78 ± 0.08 μM) inhibited tyrosinase more than kojic acid (49.39 ± 0.17 μM), and docking study indicated compound Z8 (-7.32 kcal/mol) had stronger binding affinities for tyrosinase than kojic acid (-5.7 kcal/mol). Phenolic hydroxyl group on 4-position (R2) of compound Z8 can form Metal - Acceptor with Cu401. The results of inhibition kinetics studies demonstrated that compound Z8 was mixed type inhibitor. The anti-browning effects manifested compound Z8 expressed satisfactory effects in anti-browning of fresh-cut apples and fresh-cut potato. All the results indicated that thiazole Schiff base derivatives might be promising leading compounds as tyrosinase inhibitors and anti-oxidant agents.
- Zhou, Wei,Wu, Fengyan,Liu, Jinbing
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p. 1337 - 1353
(2021/07/21)
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- Design, synthesis and molecular modelling studies of 1-methyl-3-(4-substituted phenyl-1,3thiazol-2-yl)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1h)-ones as potent anticancer agents
-
The present study involves the design, synthesis, characterization and molecular docking studies of biologically active quinazolin-4-ones, which were synthesized by condensing 2-amino-4-substituted phenylthiazole with N-methylbenzoxazin-4-one. The N-methylbenzoxazin-4-one and 2-amino-4-substituted phenylthiazole were synthesized from N-methylanthranilic acid and substituted ketones, respectively. The ADME properties determined the synthetic accessibility of quinazolin-4-ones by in silico Swiss ADME. The colorectal anticancer screening was done by using cell HT-29 human colorectal adenocarcinoma based on molecular docking studies on 3GC7-the structure of p38alpha in complex with dihydroquinazolinone. Finally, compounds 5Dh8, 5DF6, 5Db2 and 5Di9 exhibited better activity at a concentration 10 μg/mL when compared to 5-fluorouracil. The ADME properties revealed that all the compounds were within the range and docking studies showed the highest binding with glide score -7.19 and -7.027 Kcal/mol compared to the target protein -10.67 Kcal/mol.
- Nagaladinne, Nizamuddin,Hindustan, Abdul Ahad,Nayakanti, Devanna
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p. 3067 - 3074
(2021/01/06)
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- Synthesis and Molecular Docking Studies of Some 1,2-Dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydroquinazolin-4(1H)-ones as Anticancer Agents
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Synthesis of 1, 2-dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydro quinazolin-4(1H)-ones (5Aa1-5Ak11) derivatives was effected by refluxing 1,2-dimethylbenzoxazine-4-one with different 4-substituted phenyl-1,3-thiazol-2-amines. Synthesized compounds were characterized through elemental analysis, infrared, proton nuclear magnetic resonance, and Carbon-13 nuclear magnetic resonance. Molecular docking studies were carried out using Schr?dinger Glide (version 2020_1) which was docked into selective P38alpha and Activin A Receptor Type 1 (ACVR1) Activin receptor-like kinase-2 (ALK2) kinase with Protein Data Bank (PDB) code 3GC7, 6GI6. Based on the docking score of synthesized quinazolin-4-one derivatives, co-crystallized ligands interaction was evaluated with 5-fluorouracil (5-FU) as a reference drug. Compounds 5Ae5, 5Aa1, 5Ai9, and 5Ab2 with P38alpha, 5Af6, 5Ae5, 5Ad4, and 5Ab2 with ACVR1 (ALK2) kinase score were -7.265, -7.078, -7.058, and -6.836; -8.929, -8.749, -8.735, and -8.464 Kcal/mol against enzymes responsible for cancer treatment. The results indicated that quinazolin-4-one derivatives had scored better than ligand and 5-FU.
- Nizamuddin,Ahad, Hindustan Abdul,Devanna, Nayakanti
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p. 571 - 579
(2021/02/02)
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- Asparagine functionalized Al2O3 nanoparticle as a superior heterogeneous organocatalyst in the synthesis of 2-aminothiazoles
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Asparagine functionalized aluminum oxide nanoparticles (Asp-Al2O3) have been prepared by a two-step procedure involving the grafting of Al2O3 with 3-chloropropyltrimethoxysilane (CPTMS) and subsequent organofunctionalization using asparagine amino acid. It is shown that Asp-Al2O3 exhibits as an active nanocatalyst for the preparation of 2-aminothiazoles is achieved by one-pot reaction of methylcarbonyls, thiourea and iodine. The structure of Asp-Al2O3 was characterized by fourier transform infrared radiation (FT-TR), thermal gravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopic (SEM), and energy-dispersive analysis of X-ray (EDAX) analyses. Advantages of this modified methodology include higher purity and excellent yield of products, greener and cleaner conditions, easy isolation of products and convenient manipulation. Moreover, immobilization of organocatalysts on the Al2O3 surface are stable under the catalytic reaction conditions resulting their efficient reuse.
- Zarnegar, Zohre,Shokrani, Zahra,Safari, Javad
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p. 143 - 152
(2019/03/14)
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- Thiazole drug molecule with bactericidal activity and preparation method thereof
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The invention discloses a thiazole drug molecule with bactericidal activity and a preparation method thereof, and belongs to the technical field of synthesis of antibacterial drugs. The thiazole drugmolecule is technically characterized in that the thiazole drug molecule has a structure, wherein R represents methyl, hydroxyl or nitro. According to the thiazole drug molecule, 4-methylacetophenoneis used as an initial raw material, 4-(4-methylbenzene)-thiazole-2-amine is obtained through primary cyclization at first, 3-(4-methylbenzene)-5H-thiazole[3,2-a]pyrimidin-5-ketone is obtained throughsecondary cyclization, 6-hydroxymethyl-3-(4-methylbenzene)-5H-thiazole[3,2-a]pyrimidin-5-ketone is obtained through a reaction with paraformaldehyde, and finally, a target compound is obtained throughtwo-step oxidation, one-step acylation and other processes. An antibacterial activity test is carried out through an Oxford cup agar diffusion method, and it is found that the target compound has a good inhibition effect on escherichia coli and bacillus subtilis.
- -
-
Paragraph 0039-0041
(2019/09/05)
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- Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors
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Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.
- Dai, Weiyang,Samanta, Soma,Xue, Ding,Petrunak, Elyse M.,Stuckey, Jeanne A.,Han, Yanyan,Sun, Duxin,Wu, Yong,Neamati, Nouri
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p. 3068 - 3087
(2019/03/07)
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- MNPs@SiO2-Pr-AP: A new catalyst for the synthesis of 2-amino-4-aryl thiazole derivatives
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A simple and efficient synthesis of 2-amino-4-aryl thiazole derivatives was carried out through the reaction of substituted acetophenones and thiourea using three different types of catalytic systems including N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and a combination of TBBDA and nano-magnetic catalyst supported with functionalized 4-amino-pyridine silica (MNPs@SiO2-Pr-AP). The results showed that the use of TBBDA along with the MNPs@SiO2-Pr-AP gains the highest yields of the products in the shortest reaction time.
- Ghorbani-Vaghei, Ramin,Alavinia, Sedigheh,Merati, Zohreh,Izadkhah, Vida
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-
- 4-Phenyl-1,3-thiazole-2-amines as scaffolds for new antileishmanial agents
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Background: There is still a need for new alternatives in pharmacological therapy for neglected diseases, as the drugs available show high toxicity and parenteral administration. That is the case for the treatment of leishmaniasis, particularly to the cutaneous clinical form of the disease. In this study, we present the synthesis and biological screening of eight 4-phenyl-1,3-thiazol-2-amines assayed against Leishmania amazonensis. Herein we propose that these compounds are good starting points for the search of new antileishmanial drugs by demonstrating some of the structural aspects which could interfere with the observed activity, as well as suggesting potential macromolecular targets. Methods: The compounds were easily synthesized by the methodology of Hantzsch and Weber, had their purities determined by Gas Chromatography-Mass spectrometry and assayed against the promastigote forms of Leishmania amazonensis as well as against two white cell lines (L929 and THP-1) and the monkey's kidney Vero cells. PrestoBlue and MTT viability assays were the methodologies applied to measure the antileishmanial and cytotoxic activities, respectively. A molecular modeling target fishing study was performed aiming to propose potential macromolecular targets which could explain the observed biological behavior. Results: Four out of the eight compounds tested exhibited important anti-promastigote activity associated with good selectivity indexes when considering Vero cells. For the most promising compound, compound 6, IC50 against promastigotes was 20.78 while SI was 5.69. Compounds 3 (IC50: 46.63μM; SI: 26.11) and 4 (IC50: 53.12μM; SI: 4.80) also presented important biological behavior. A target fishing study suggested that S-methyl-5-thioadenosine phosphorylase is a potential target to these compounds, which could be explored to enhance activity and decrease the potential toxic side effects. Conclusions: This study shows that 4-phenyl-1,3-thiazol-2-amines could be good scaffolds to the development of new antileishmanial agents. The S-methyl-5-thioadenosine phosphorylase could be one of the macromolecular targets involved in the action.
- Rodrigues, Carina Agostinho,dos Santos, Paloma Freire,da Costa, Marcela Oliveira Legramanti,Pavani, Thais Fernanda Amorim,Xander, Patrícia,Geraldo, Mariana Marques,Mengarda, Ana,de Moraes, Josué,Rando, Daniela Gon?ales Galasse
-
-
- Novel 1,3,5-triazine derivatives exert potent anti-cervical cancer effects by modulating Bax, Bcl2 and Caspases expression
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This study aimed to develop novel 1,3,5-triazine derivatives as potent anti-cervical cancer agents. The compounds were synthesized in short steps with an excellent yield and characterized via various spectroscopic and analytical methods. A structure–activity relationship study suggested that electron-withdrawing substituents showed greater anticancer activity than electron-donating groups. Compound 7p (p-fluoro) showed the highest activity against cervical cancer cells. In a nude mouse xenograft model inoculated with HeLa cells, 7p showed dose-dependent inhibition of cervical tumour growth. Histopathological examination of excised tumour-bearing tissues showed that 7p improved the microstructure in a dose-dependent manner. Compound 7p also increased the proportions of HeLa cells in G0/G1 and S-phase and significantly decreased that of G2/M-phase. The effects of 7p on C-caspase-3, C-caspase-9, Bcl-2 and Bax expression in HeLa cells were also determined.
- Wang, Xiwen,Yi, Yuexiong,Lv, Qiongying,Zhang, Juan,Wu, Kejia,Wu, Wanrong,Zhang, Wei
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p. 728 - 734
(2017/11/21)
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- Nanostarch: a novel and green catalyst for synthesis of 2-aminothiazoles
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Abstract: In this work, starch nanoparticles as a green and cheap catalyst were obtained based on the precipitation of amorphous starch in ethanol. It was found that starch nanoparticles are efficient catalyst for the synthesis of 2-aminothiazoles using methylcarbonyl compounds and thiourea as precursors. The use of green and biodegradable nanostarch makes this present methodology quite simple, shorter reaction times and milder conditions, and more convenient and economically viable compared to catalyzed methods reported in the literature. Graphical abstract: [Figure not available: see fulltext.]
- Safari, Javad,Sadeghi, Masoud
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p. 745 - 749
(2017/03/17)
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- C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay
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In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.
- Zarnegar, Zohre,Alizadeh, Roghayeh,Ahmadzadeh, Majid,Safari, Javad
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- Design and development of some thiazole-based flavanoids as novel antibacterial against pathogens causing surgical site infection for possible benefit in bone trauma via inhibition of DNA gyrase
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In this study, a novel class of hybrid thiazole-based flavanoid derivatives were synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, mass and elemental analysis. These derivatives were evaluated for antibacterial activity for possible benefit in bone trauma via inhibition of DNA gyrase enzyme. Results suggested that compounds 9n, 9o, and 9p showed considerable inhibition of DNA gyrase with considerable activity against tested forty strains of Staphylococcus aureus clinical isolates. Moreover, compound 9n showed hydrogen bonding with LYS460 along with low binding free energy of ?4.36?kcal/mol against DNA gyrase enzyme. The hemolytic activity of the potent compounds showed mild to no activity together with excellent pharmacokinetics, suggesting to have a potential for the development of designed compounds as novel antibacterial agents.
- Zhao, Gang,Lan, Dengzhe,Qi, Guobao
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p. 778 - 790
(2017/11/15)
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- Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach
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An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.
- Gundala, Trivikram Reddy,Godugu, Kumar,Nallagondu, Chinna Gangi Reddy
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p. 1408 - 1416
(2017/10/23)
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- Nanochitosan: A biopolymer catalytic system for the synthesis of 2-aminothiazoles
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A convenient and efficient method is described for the synthesis of 2-aminothiazoles by one-pot reaction of ketone and thiourea using chitosan nanoparticles under mild condition. Nanochitosan was used as a biodegradable and green catalyst for this reaction in satisfactory yields. The attractive advantages of the present process include easy isolation of products, milder and cleaner conditions, higher purity and yields and easier work-up procedure.
- Safari, Javad,Abedi-Jazini, Zahra,Zarnegar, Zohre,Sadeghi, Masoud
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p. 108 - 112
(2016/02/05)
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- Synthesis of 2-aminothiazoles from methylcarbonyl compounds using a Fe3O4 nanoparticle-: N -halo reagent catalytic system
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An efficient protocol is developed for the synthesis of 2-aminothiazoles from unfunctionalized methylcarbonyl compounds using Fe3O4 nanoparticle-N-halo reagent catalytic systems. 1,3-dichloro-5,5-dimethylhydantoin (DCDMH), N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) as N-halo reagents were explored and the best results were obtained for DCDMH. Fe3O4 nanoparticle-DCDMH as an active, reusable, excellent, highly stable magnetic catalyst was used in this process. Advantages of this efficient method include greener and cleaner conditions, shorter reaction time, excellent yield of products, easy separation using a simple external magnetic field, low cost and operational simplicity.
- Sadeghi, Masoud,Safari, Javad,Zarnegar, Zohre
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p. 64749 - 64755
(2016/07/21)
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- Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles
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An efficient one-pot synthesis of 2-aminothiazoles from methylcarbonyl and thiourea has been developed using montmorillonite-K10 as a catalyst at 80?°C in DMSO medium. A plausible mechanism is proposed in which α-iodomethylcarbonyls are formed via methylcarbonyls as raw material using iodine as iodination reagent.
- Safari, Javad,Sadeghi, Masoud
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p. 8175 - 8183
(2016/11/25)
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- Design and Synthesis of 3-Substituted-thiazolyl-2-iminothiazolidin-4-ones as a New Class of Anticonvulsants
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A new series of 3-substituted-thiazolyl-2-iminothiazolidin-4-ones were synthesized by nucleophilic substitution of p-substituted-thiazol-2-yl-chloroacetamides with potassium thiocyanide by cyclization. The starting material p-substituted-thiazol-2-yl-chloroacetamides were synthesized from p-substituted-thiazol-2-yl-amines with chloroacetyl chloride, which in turn was prepared from one pot reaction of substituted aryl acetophenone and amino group of thiourea. The title compounds were investigated for their anticonvulsant activity. Among the tested compounds, compound 3-(4-(4-fluorophenyl)thiazol-2-yl)-2-iminothiazolidin-4-one (16) emerged as the most active compound of the series, and it is moderately more potent than the reference standard diazepam.
- Alagarsamy,Senthilraja,Raja Solomon
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p. 1635 - 1639
(2016/09/23)
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- 2-amino-4-arylthiazole derivatives as anti-giardial agents: Synthesis, biological evaluation and QSAR studies
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A series of seven 2-amino-4-arylthiazoles were prepared following Hantzsch's modified method under microwave irradiation. A set of 50 derivatives was obtained and the in vitro activity against Giardia intestinalis was evaluated. The results on the biological activity revealed that, in general, the N-(5-bromo-4-aryl-thiazol-2-yl)-acetamide scaffold showed high bioactivity. In particular, compounds 6e (IC50= 0.39 μM) and 6b (IC50= 0.87 μM) were found to be more potent than the positive control metronidazole. Citoxicity and acute toxicity tests performed showed low toxicity and high selectivity of the most active compounds (6e SI = 139, 6b SI = 52.3). A QSAR analysis was applied to a data set of 37 obtained 2-amino-4-arylthiazoles derivatives and the best model described a strongly correlation between the anti-giardiasic activity and molecular descriptors as E2M, RDF115m, F10, MATS6v, and Hypnotic-80, with high statistical quality. This finding indicates that N-substituted aminothiazole scaffold should be investigated for the development of highly selective anti-giardial agent.
- Mocelo-Castell, Raul,Villanueva-Novelo, Carlos,Cáceres-Castillo, David,Carballo, Ruben M.,Quijano-Qui?ones, Ramiro F.,Quesadas-Rojas, Mariana,Cantillo-Ciau, Zulema,Cedillo-Rivera, Roberto,Moo-Puc, Rosa E.,Moujir, Laila M.,Mena-Rejón, Gonzalo J.
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p. 1127 - 1136
(2016/08/10)
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- A Potent and Site-Selective Agonist of TRPA1
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TRPA1 is a member of the transient receptor potential (TRP) cation channel family that is expressed primarily on sensory neurons. This chemosensor is activated through covalent modification of multiple cysteine residues with a wide range of reactive compounds including allyl isothiocyanate (AITC), a spicy component of wasabi. The present study reports on potent and selective agonists of TRPA1, discovered through screening 1657 electrophilic molecules. In an effort to validate the mode of action of hit molecules, we noted a new TRPA1-selective agonist, JT010 (molecule 1), which opens the TRPA1 channel by covalently and site-selectively binding to Cys621 (EC50 = 0.65 nM). The results suggest that a single modification of Cys621 is sufficient to open the TRPA1 channel. The TRPA1-selective probe described herein might be useful for further mechanistic studies of TRPA1 activation.
- Takaya, Junichiro,Mio, Kazuhiro,Shiraishi, Takuya,Kurokawa, Tatsuki,Otsuka, Shinya,Mori, Yasuo,Uesugi, Motonari
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supporting information
p. 15859 - 15864
(2016/01/09)
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- Synthesis, characterization, biological activity, and 3D-QSAR studies on some novel class of pyrrole derivatives as antitubercular agents
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A new series of pyrrole derivatives have been designed, synthesized, and their structures have been elucidated along with the evaluation of antitubercular activity against Mycobacterium tuberculosis H37Rv using the microplate alamar blue assay method and antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, and Escherichia coli by broth micro-dilution assay method. Structural activity relationships and 3D-QSAR analysis have been carried out by Topomer Comparative Molecular Field Analysis (CoMFA). Training set of 42 and test set of 8 active compounds were used to develop the method that showed cross-validated correlation coefficient (q 2) of 0.815, standard error of prediction of 0.36, non-cross-validated correlation coefficient (r 2) of 0.973, and standard error of estimate of 0.14 with six components. Graphical Abstract: Synthesis; spectral and 3D-QSAR studies; and antibacterial, antitubercular, and cytotoxic activities of a novel series of pyrrole derivatives are described.[Figure not available: see fulltext.]
- Joshi, Shrinivas D.,More, Uttam A.,Dixit, Sheshagiri R.,Korat, Haresh H.,Aminabhavi, Tejraj M.,Badiger, Aravind M.
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p. 1123 - 1147
(2014/03/21)
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- Facile and efficient preparation of hybrid phenylthiazolyl-1,3,5-triazines and their antidepressant-like effect in mice
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High safety, robust efficacy, and rapid onset of action remain the key challenges for improving antidepressant drug discovery. We report a facile and efficient synthetic strategy to structurally encompass mono-, di-, or tri-substituted derivatives using cyanuric chloride and various substituted phenylthiazole-2-amines. The predicted physicochemical property precisely state their specificity as CNS acting agent and antidepressant-like effect of the most promising compound 10 after oral administration significantly reduced immobility in mice behavior models, especially TST from 63 s. In addition, good safety features of 10 highlight its ability to modulate hallmarks for antidepressant discovery. These insights are useful in generalization and systematization of CRF1antagonist design to develop future biological end points.
- Gahtori, Archana,Kumar, Abhay,Kothiyal, Preeti,Gahtori, Prashant
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p. 4987 - 4990
(2015/02/02)
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- Antioxidant and DNA damage inhibition activities of 4-Aryl-N-(4-aryl-thiazol-2-yl)-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxamides
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A series of 4-aryl-N-(4-pheny-thiazol-2-yl)-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxamides were synthesized by condensing 4-aryl-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxylic acid with 2-amino-4-aryl-thiazole derivatives. The newly synthesized molecules were characterized by spectral analysis and subjected to antioxidant and DNA damage inhibition studies.
- Shubakara,Umesha,Srikantamurthy,Chethan
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p. 1913 - 1921
(2015/02/05)
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- Solvent-free synthesis of 2-amino-4-arylthiazoles under microwave irradiation
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2-Amino-4-arylthiazoles were prepared in a one-pot solvent-free procedure by reaction of p-substituted acetophenones with thiourea and iodine under microwave irradiation.
- Cáceres-Castillo, David,Carballo, Rubén M.,Tzec-Interián, Jorge A.,Mena-Rejón, Gonzalo J.
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experimental part
p. 3934 - 3936
(2012/08/14)
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- The design, synthesis and antimicrobial activity of new biquinoline derivatives
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A simple and efficient method has been developed for the synthesis of some novel biquinoline derivatives bearing a thiazole moiety through a onepot three-component condensation of 2-chloro-3-formylquinolines, ethyl cyanoacetate and a β-enaminone using a catalytic amount of piperidine in refluxing ethanol. These molecules were evaluated in vitro for their antibacterial and antifungal activity. Most of the compounds exhibited moderate antibacterial and antifungal activity against all the tested strains.
- Shah, Nirav K.,Shah, Nimesh M.,Patel, Manish P.,Patel, Ranjan G.
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scheme or table
p. 279 - 286
(2012/06/01)
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- Synthesis, characterization and antimicrobial activity of some new biquinoline derivatives containing a thiazole moiety
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A series of new biquinoline derivatives containing a thiazole moiety were synthesized by a one-pot, base-catalyzed cyclocondensation reaction of 2-chloro-3-formyl quinoline, malononitrile and enaminone. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR data. All the synthesized compounds were screened against three bacterial pathogens, namely Bacillus cereus, B. substilis and Escherichia coli and for antifungal activity against three fungal pathogens, Aspergillus niger, Fusarium oxisporum and Rhizopus using the disc diffusion method.. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
- Shah, Nirav K.,Shah, Nimesh M.,Patel, Manish P.,Patel, Ranjan G.
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scheme or table
p. 454 - 457
(2012/06/01)
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- I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea
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A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a-f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds 3c and 5b were further determined by X-ray crystallographic analysis.
- Zhu, Yan-Ping,Yuan, Jing-Jing,Zhao, Qin,Lian, Mi,Gao, Qing-He,Liu, Mei-Cai,Yang, Yan,Wu, An-Xin
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supporting information; experimental part
p. 173 - 178
(2012/01/05)
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- Synthesis of 2-(sulfamoylphenyl)-4′-(iminoaryl/hetroaryl)-4- (4′′-hydroxyphenyl)-thiazoles and their O-glucosides
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In continuation of our work, we synthesized 2-(sulfamoylphenyl)-4′- amino-4-(4″-hydroxyphenyl)-thiazole (3a), which were reacted with various (aryl/hetroaryl) aldehyde to form 2-(sulfamoylphenyl)-4′-(iminoaryl/ hetroaryl)-4-(4″-hydroxyphenyl)-thiazoles (4
- Taile,Hatzade,Ingle
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experimental part
p. 1428 - 1433
(2011/12/21)
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- Synthesis of 2-(Substituted benzylideneamino)-4-(4'-hydroxyphenyl) thiazoles and their O-glucosides
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2-Amino-4-(4'-hydroxyphenyl) thiazole 1a was prepared from reaction between p-hydroxyacetophenone, thiourea, and iodine; compound 1a was treated with several (aryl/hetro aryl) aldehydes to form 2-(substituted benzylideneamino)-4- (4'-hydroxyphenyl) thiazo
- Taile,Ingle,Hatzade
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experimental part
p. 207 - 221
(2011/05/02)
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- Preparation, antimicrobial activity, and toxicity of 2-amino-4-arylthiazole derivatives
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Seven 2-amino-4-aryl-1,3-thiazoles (1a-g) and their corresponding 2-aminoacetyl (2a-g) and 2-aminoacetyl-5-bromo (3a-g) derivatives were synthesized and tested in vitro against 11 reference strains, three Gram-positive and four Gram-negative bacteria, two yeasts, and two moulds. Toxicity of the compounds was also evaluated using the brine shrimp test. Compounds 1a, 1b, 1e-g, and 3b showed moderate antimicrobial activity at different concentrations. The results indicated that acetylation of the amino group and bromination at position 5 of the thiazole moiety cause lost of activity. Compounds 1a, 1e, and 1f showed toxicity to brine shrimp nauplii below 10 ppm. Most other compounds showed moderate toxicity, LD50 above 100 ppm. Structures of all compounds were confirmed by NMR and MS data.
- Morales-Bonilla, Pedro,Perez-Cardena, Andrea,Quintero-Marmol, Esther,Arias-Tellez, Jose Luis,Mena-Rejon, Gonzalo J.
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p. 254 - 260
(2007/10/03)
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- Anti-herpesvirus compounds and methods for identifying, making and using same
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This invention relates to methods for inhibiting herpes replication and for treating herpes infection in a mammal by inhibiting the herpes helicase-primase enzyme complex. This invention also relates to thiazolyphenyl derivatives that inhibit the herpes helicase-primase and to pharmaceutical compositions comprising the thiazolylphenyl derivatives, to methods of using and methods of producing the thiazolylphenyl derivatives.
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- Reaction of 2-Aminothiazoles with 5-Oxazolones
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2-Phenyl-oxazolin-5-one (1a) reacts with 2-aminothiazoles (2) to give 3. 4-Ethoxymethylene-(2-phenyl)-oxazolin-5-one (1b) with 2 forms 4. 4-Benzylidene-2-oxazolin-5-one (1c) fails to react.
- Tikdari, Ahmad M.,Mukerjee, Arya K.
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p. 478 - 479
(2007/10/02)
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- Studies of arylthiazole oxamates in relation to oral antiallergic activity
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25 arylthiazole oxamate derivatives were synthesized and examined for antiallergic activity in the rat passive cutaneous anaphylaxis assay. These compounds were prepared by treatment of the appropriate bromoacetophenone with thioureas to give arylaminothiazoles. Further condensation with alkyloxalyl chloride gave the arylthiazolyl oxamates. Several derivatives showed a 70% inhibition at 5 mg/kg p.o. p-Alkoxy substitution on the phenyl ring resulted in enhanced activity while N-alkyl substitution on the nitrogen amide function inhibited the activity. Ethyl-N-(4-p-methoxyphenyl)-2-thiazolyl oxamate (tioxamast, F-1865) was selected for clinical studies.
- Cousse,Mouzin,Bonnaud,Tarayre,Couzinier
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p. 1391 - 1393
(2007/10/02)
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