2929-81-9Relevant articles and documents
Facile synthesis of novel fluorescent thiazole coumarinyl compounds: Electrochemical, time resolve fluorescence, and solvatochromic study
Ahmad, Zahoor,Arshad, Ifzan,Bahadur, Ali,Channar, Pervaiz Ali,Iqbal, Shahid,Irfan, Rana Muhammad,Javed, Mohsin,Khalid, Bilal,Liu, Guocong,Mahmood, Qaiser,Qayyum, Muhammad Abdul,Raheel, Muhammad,Rizwan, Komal,Saeed, Aamer,Saifullah, Muhammad,Shabir, Ghulam,Shoaib, Muhammad,Ujan, Rabail
, (2021)
In this study, Benzocoumarin-Thiazoles-Azomethine derivatives with bioactive scaffolds were synthesized and characterized. The present investigation is concerned with the multistep synthesis of thiazole coumarinyl derivatives (5a-k), which were accomplished from naphthaldehyde, ethyl acetoacetate, and thiosemicarbazide. The formation of newly synthesized derivatives was confirmed by 1H NMR and 13C NMR spectroscopic studies. Thiazole coumarinyl derivatives were subjected to UV-Visible studies in different solvents such as ethanol, ethyl acetate, and DMF for solvatochromic studies. The synthesized coumarinyl thiazole compounds showed absorption in the range of 332-390 nm. Electrochemical studies were performed in DMSO and redox behavior was offered by thiazoles. Fluorescence of coumarinyl thiazole compounds were examined in ethanol, ethyl acetate, and DMF to visualize the solvent effect on the emitting ability of compounds. Fluorescence spectra of coumarinyl thiazoles expressed a sharp emission in the range 436-550 nm.
Crystal structure and conformation study of 4-N,N-dimethylamine benzaldehyde thiosemicarbazone derivative
Sampath,Mathews, Rita,Ponnuswamy,Kang, Lin-Woo
, p. 151 - 159 (2010)
Thiosemicarbazones are N-N-S donor ligands having the ability to bind metal ions and inhibit ribonucleoside reductase, an enzyme important for DNA synthesis of all the mammalian cells. One of the important phenyl thiosemicarbazones, the title compound, ha
Adsorption and inhibitor action of 4-(N,N-dimethylamino) benzaldehyde thiosemicarbazone on 6061 Al/SiC composite and its base alloy in sulfuric acid medium
Pinto, Geetha Mable,Nayak, Jagannath,Shetty, A. Nityananda
, p. 127 - 140 (2011)
The inhibitive action of 4-(N,N-dimethylamino)benzaldehyde thiosemicarbazone (DMABT) on the corrosion behavior of 6061 Al -15 vol. pct. SiC(p) composite and its base alloy was studied at different temperatures in sulfuric acid medium containing varying co
Application of bioisosterism in design of the semicarbazone derivatives as cruzain inhibitors: a theoretical and experimental study
Vital, Drielli G.,Damasceno, Flávia S.,Rapado, Ludmila N.,Silber, Ariel M.,Vilella, Filipe S.,Ferreira, Rafaela S.,Maltarollo, Vinícius G.,Trossini, Gustavo H. G.
, p. 1244 - 1259 (2017)
A series of semicarbazone, thiosemicarbazone, and aminoguanidine derivatives were synthesized and tested as antitrypanosomal agents. The theoretical NMR of the compounds was calculated using molecular modeling techniques (density functional theory (DFT) calculations) and confirmed the formation of the compounds. The ability to inhibit cruzain and Trypanosoma cruzi epimastigote replication was evaluated. Cruzain inhibition ranged between 70 and 75% (100?μM), and IC50 values observed in epimastigote forms of T. cruzi ranged from 20 to 140?μM. Furthermore, the compounds did not present cytotoxicity at concentrations up to 50 and 250?μM in MTT tests. Molecular modeling studies were conducted using DFT method (B3LYP functional and the basis set 6-311G(d,p)) to understand the activity of the compounds, corroborating the observed cruzain inhibitory activity. In docking studies, the obtained analogs showed good complementarity with cruzain active site. In addition, docking results are in accordance with the susceptibility of these analogs to nucleophilic attack of the catalytic Cys25. Taken together, this study shows that this class of compounds can be used as a prototype in the identification of new antichagasic drugs.
Thiosemicarbazone Derivatives as Inhibitors of Amyloid-β Aggregation: Effect of Metal Coordination
Caballero, Ana B.,Espargaró, Alba,Gamez, Patrick,Lorenzo, Carmen,Matesanz, Ana I.,Quiroga, Adoración G.,Sabaté, Raimon
, (2020)
Three thiosemicarbazone derivatives, namely 4-(dimethylamino)benzaldehyde 4,4-dimethylthiosemicarbazone (HL1), 4-(dimethylamino)benzaldehyde thiosemicarbazone (HL2), and 4-(dimethylamino)benzaldehyde 4-methylthiosemicarbazone (HL3), have been synthesized and characterized. The three palladium(II) complexes 1-3 were prepared respectively from HL1, HL2, and HL3. The crystal structures of two coordination compounds, namely Pd(L2)2 (2) and Pd(L3)2 (3), were obtained, which showed the expected square-planar environment for the metal centers. The ligand HL3 and the Pd(II) complexes 1-3, which are stable in buffered solutions containing up to 5% DMSO, exhibit remarkable inhibitory properties against the aggregation of amyloid-β, reducing the formation of fibrils. HL1, HL3, 2, and 3 display IC50 values (i.e., the concentrations required to reduce Aβ fibrillation by 50%) below 1 μM, lower that of the reference compound catechin (IC50 = 2.8 μM). Finally, in cellulo studies with E. coli cells revealed that the palladium(II) compounds are significantly more efficient than the free ligands in inhibiting Aβ aggregation inside bacterial inclusion bodies, thus illustrating a beneficial effect of metal coordination.
Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs
Ullah, Hayat,Liaqat, Anjum,Khan, Qudrat Ullah,Taha, Muhammad,Khan, Fahad,Rahim, Fazal,Uddin, Imad,Rehman, Zia Ur
, p. 213 - 224 (2021/09/09)
A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]
Synthesis, antimicrobial and antioxidant evaluation with in silico studies of new thiazole Schiff base derivatives
Ahmed, Junaid Uddin,Al-Macktuf, Abdullah,Haque, Md. Aminul,Islam, Md. Din,Nishino, Hiroshi,Rahman, Mohammad Mostafizur,Shah, Md. Shahazada
, (2021/10/19)
A series of nineteen thiazole Schiff base derivatives 2a-2s were synthesized (Scheme 1) and elucidated by spectral analyses (IR, 1H NMR and HRMS). The evaluation of their antimicrobial activities against two gram-positive, two gram-negative, an
Discovery of new coumarin-based lead with potential anticancer, cdk4 inhibition and selective radiotheranostic effect: Synthesis, 2d & 3d qsar, molecular dynamics, in vitro cytotoxicity, radioiodination, and biodistribution studies
Sarhan, Mona O.,Abd El-Karim, Somaia S.,Anwar, Manal M.,Gouda, Raghda H.,Zaghary, Wafaa A.,Khedr, Mohammed A.
, (2021/05/13)
Novel 6-bromo-coumarin-ethylidene-hydrazonyl-thiazolyl and 6-bromo-coumarin-thiazolylbased derivatives were synthesized. A quantitative structure activity relationship (QSAR) model with high predictive power r2 = 0.92, and RMSE = 0.44 predicted five compounds; 2b, 3b, 5a, 9a and 9i to have potential anticancer activities. Compound 2b achieved the best ?G of –15.34 kcal/mol with an affinity of 40.05 pki. In a molecular dynamic study 2b showed an equilibrium at 0.8 ? after 3.5 ns, while flavopiridol did so at 0.5 ? after the same time (3.5 ns). 2b showed an IC50 of 0.0136 μM, 0.015 μM, and 0.054 μM against MCF-7, A-549, and CHO-K1 cell lines, respectively. The CDK4 enzyme assay revealed the significant CDK4 inhibitory activity of compound 2b with IC50 of 0.036 μM. The selectivity of the newly discovered lead compound 2b toward localization in tumor cells was confirmed by a radioiodination biological assay that was done via electrophilic substitution reaction utilizing the oxidative effect of chloramine-t.131 I-2b showed good in vitro stability up to 4 h. In solid tumor bearing mice, the values of tumor uptake reached a height of 5.97 ± 0.82%ID/g at 60 min p.i.131 I-2b can be considered as a selective radiotheranostic agent for solid tumors with promising anticancer activity.
Design and efficient synthesis of novel 4,5-dimethylthiazole-hydrazone derivatives and their anticancer activity
Evren, Asaf Evrim,Yurtta?, Leyla,Ekselli, Bü?ra,Aksoy, Onur,Akalin-?ift?i, Gül?en
, p. 372 - 386 (2021/06/17)
Background: Recently, researchers have been warning about the increased mortality of the various cancer types. Also, the lung adenocarcinoma and the glioma types are burning issues for world's health due to late or wrong diagnosis and/or insufficient treatment methods. For this purpose, our research group designed and synthesized novel 4,5-dimethyl thiazole-hydrazone derivatives which were tested against cancer and normal cell lines to understand the structure-activity relationship (SAR). Methods: The lead compounds were obtained by reacting 2-(substituted aryl-2-ylmethylene) hydrazin-1-carbothioamide with 3-chloro-2-butanone derivatives. The structural elucidation of the compounds was performed by1H-NMR,13C-NMR, and LC/MS-IT-TOF spectral and elemental analyses. The synthesized compounds were tested in vitro for the anticancer activity against A549 human lung adenocarcinoma and C6 rat glioma cells and investigated for which pathway to induce cell death. Also, the docking study of the active compounds was achieved to understand the SAR. Results: The targeted compounds (2a-2l) were synthesized successfully above 70% yields, and the analysis findings proved their purity. In general, the results of activity studies displayed significant effects against at least one cell line, except compounds 2e (indol-3-yl) and 2h (4-dimethylaminophenyl). Furthermore, compounds 2b and 2f displayed potential anticancer activity. With the help of molecular docking study, a potential selectivity of compound 2f was observed for type II protein kinase. On the other hand, compound 2b interacted with the active site nearly the same as Dasatinib. Therefore, these two compounds could be used as a base on developing selective anticancer drugs. Conclusion: Pyridin-2-yl (2b) derivative was found to be a favorable molecule with high anticancer potency against C6 and A549 cell lines. Additionally, 1-naphthyl (2f) derivative was a worthy compound for potential selectivity. In future studies, it will be our priority to focus on developing derivatives of these two compounds (2b and 2f) and elucidate their mechanisms.
Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-D-hexosaminidase and chitinase
Yang, Huibin,Qi, Huitang,Hao, Zesheng,Shao, Xusheng,Liu, Tian,Yang, Qing,Qian, Xuhong
, p. 1271 - 1275 (2019/12/24)
Insect chitinase and N-acetyl-β-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R1 at N3) and II (with substituted group R1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R1, demonstrated the best inhibitory activities against OfHex1 and OfChi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (Ki = 1.5 μmol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (Ki = 5.9 μmol/L). The differences in compounds’ binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (Ki = 1.9 μmol/L) and II-3d (Ki = 4.1 μmol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors.
