555-90-8Relevant academic research and scientific papers
Synthesis, Antioxidant, and Antibacterial Studies of Zn(II), Cd(II), and Hg(II) Complexes with 3-Formylpyridinethiosemicar bazone and Its N 4-Methyl Analogue
Mydhili,Sireesha,Reddy, Ch. Venkata Ramana
, p. 1015 - 1022 (2019)
Evaluation of stability constants of the complexes formed in solution by the biologically important ligands and metal ions can aid in understanding the application of metal complexes in chelation therapy. Hence, complexation equilibrium studies of the ligands (L), 3-formylpyridinethiosemicarbazone (H3FPT) and 3-formylpyridine-N4-methylthiosemicarbazone (H3FP4MT) with Zn(II) and Cd(II) metal ions (M) are carried out in 70% v/v DMF-water medium at 0.1M KNO3 ionic strength and the stability constants are determined pH-metrically at 303 K. The binary complexes are formed in 1: 1 (M: L) ratio and are fairly stable. The binary complexes of H3FPT and H3FP4MT (L) with Zn(II), Cd(II) and Hg(II) ions are synthesized and characterized by various analytical and spectral techniques including elemental analysis, molar conductance, LC-MS, TGA, IR and 1H NMR spectroscopy. According to the accumulated information, the complexes are polymeric (ML)n with n > 2, except that of Hg(II)-H3FP4MT, which is ML2. The antioxidant activity of the ligands and their Zn(II) and Hg(II) complexes demonstrate higher activity than their corresponding ligands Cd(II) complexes. Antibacterial activity of the ligands and the complexes is tested against gram positive: Staphylococcus aureus, Bacillus subtilis and gram negative: Escherichia coli and Klebsiella pneumonia bacterial strains. Activity of complexes is determined to be higher than that of the corresponding free ligands.
Enhancing the electrochemical properties of the p-type conductive polymer on the surface of the new synthesized 2-(pyridin-3-ylmethylene) hydrazine-1-carbothioamide-modified electrode: computational and electrochemical study
Safari, Reza,Ehsani, Ali,Bigdelo, Mohamad,Mirtamizdoust, Babak
, p. 1441 - 1449 (2019)
Herein, 2-(pyridin-3-ylmethylene)hydrazine-1-carbothioamide(3PHCT)was first fabricated through a chemical method, and subsequently, polyorthoaminophenol (POAP)/3PHCT films were prepared using electropolymerization of POAP, carried out in the presence of the as-prepared 3PHCT to serve as the active electrode for electrochemical application. Geometry optimization and calculations of structural and electronic/vibrational properties of the 3PHCT system are studied (based on the quantum atom-in-molecule theory, QTAIM). In addition, the local intra-molecular electron density, and its Laplacian, and, thus, intra-molecular virial forces, of this molecule system are calculated. These results show that the oxygen and sulfur atoms play domain role in intra-molecular charge and energy transfer in this molecular system. In addition, based on the QTAIM, it is predicted that a single electrochemical molecular system can be grouped into p-type-like and n-type-like sections, and would be good candidate to reduce intra-molecular repulsion of the bipolaron during electrochemical polymerization of POAP. Galvanostatic charge–discharge experiments, cyclic voltammetry and electrochemical impedance spectroscopy, were conducted to characterize the prepared composite films and investigate the performance of the system, respectively. In this study, novel POAP/3PHCT are presented for electrochemical redox capacitors possessing the merits of high active surface area, stability in an aqueous electrolyte and ease of synthesis.
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
, (2020/10/27)
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.
Thiosemicarbazones exhibit inhibitory efficacy against New Delhi metallo-β-lactamase-1 (NDM-1)
Ge, Ying,Kang, Peng-Wei,Li, Jia-Qi,Gao, Han,Zhai, Le,Sun, Le-Yun,Chen, Cheng,Yang, Ke-Wu
, p. 574 - 579 (2021/07/17)
The superbug infection caused by metallo-β-lactamases (MβLs) carrying drug-resistant bacteria, specifically, New Delhi metallo-β-lactamase (NDM-1) has become an emerging threat. In an effort to develop novel inhibitors of NDM-1, thirteen thiosemicarbazones (1a-1m) were synthesized and assayed. The obtained molecules specifically inhibited NDM-1, with an IC50 in the range of 0.88–20.2 μM, and 1a and 1f were found to be the potent inhibitors (IC50 = 1.79 and 0.88 μM) using cefazolin as substrate. ITC and kinetic assays indicated that 1a irreversibly and non-competitively inhibited NDM-1 in vitro. Importantly, MIC assays revealed that these molecules by themselves can sterilize NDM-producing clinical isolates EC01 and EC08, exhibited 78-312-fold stronger activities than the cefazolin. MIC assays suggest that 1a (16 μg ml?1) has synergistic antimicrobial effect with ampicillin, cefazolin and meropenem on E. coli producing NDM-1, resulting in MICs of 4-32-, 4-32-, and 4-8-fold decrease, respectively. These studies indicate that the thiosemicarbazide is a valuable scaffold for the development of inhibitors of NDM-1 and NDM-1 carrying drug-resistant bacteria.
Hydrazine clubbed 1,3-thiazoles as potent urease inhibitors: design, synthesis and molecular docking studies
Channar, Pervaiz Ali,Saeed, Aamer,Afzal, Saira,Hussain, Dilawar,Kalesse, Markus,Shehzadi, Syeda Aaliya,Iqbal, Jamshed
, (2020/03/03)
Abstract: Synthesis of a novel series of hydrazine clubbed 1,3-thiazoles (5a–m) has been described by reacting hydrazine-1-carbothioamides (3a–k) with α-chloro- or bromo-acetophenones (4a–d) in refluxing ethanol in good to excellent yields (65–86%). Structural confirmation was based upon spectroscopic techniques such as 1H-NMR, 13C-NMR, FT-IR and mass spectrometry. The biological application of these motifs has been demonstrated in terms of their strong urease inhibition activity. The results of in vitro study revealed that all the compounds are the potent inhibitors of urease. The IC50 (ranging in between 110 and 440?nM) values were higher as compared to that of standard, i.e., thiourea (IC50 = 490 ± 10?nM). The synthesized compounds were docked at the active sites of the Jack bean urease enzyme in order to explore the possible binding interactions of enzyme–ligand complexes; the results reinforced the in vitro biological activity results. Graphic abstract: [Figure not available: see fulltext.].
Synthesis and anti-inflammatory activity of diversified heterocyclic systems
Bari, Ahmed,Grenier, Daniel,Azelmat, Jabrane,Syed, Saeed Ali,Al-Obaid, Abdulrahman M.,Hosten, Eric C.
, p. 1750 - 1759 (2019/07/16)
In continuation with our research program on the development of novel bioactive molecules, we report herein the design and synthesis of a series of diversified heterocycles (4–22). The synthesized compounds were evaluated for their anti-inflammatory activity. The chemical structures of the newly synthesized compounds have been confirmed by NMR, FTIR, and microanalysis.
Synthesis, anti-HIV activity, molecular modeling study and QSAR of new designed 2-(2-arylidenehydrazinyl)-4-arylthiazoles
Rauf, Amna,Kashif, Muhammad K.,Saeed, Bahjat A.,Al-Masoudi, Najim A.,Hameed, Shahid
, (2019/08/07)
Taking into consideration the eminence of 1,3-thiazoles in medicinal chemistry and in a view of procuring more pronounced biological contour, the synthesis of 2-(2-arylidenehydrazinyl)-4-arylthiazoles 6–43 was made possible by the cyclization reaction of thiosemicarbazones and α-bromoacetophenones. The thiosemicarbazones 5a-m were in turn synthesized from substituted benzaldehydes or acetophenones and thiosemicarbazide. Optimization of the reaction conditions was carried out in order to attain the target molecules in good yields. All the new compounds were evaluated in vitro for their antiviral activity against the replication of HIV-1 and HIV-2 in MT4 cells using a MTT assay. Screening results indicated that compounds 32–34 are the only compounds in the series inhibiting HIV-1 and HIV-2 replication in cell cultures with IC50 of >2.71, >2.19 and > 1.71 μM, respectively. The molecular docking of compounds 32 and 34 with some amino acids of human immunodeficiency virus reverse transcriptase (HIV RT) were also studied. The preliminary quantum structure-activity relationship (QSAR) among the newly synthesized congeners was obtained by two methods, Multiple Linear Regression (MRL) and Genetic Function Approximation (GFA).
New hydrazinothiazole derivatives of usnic acid as potent TDP1 inhibitors
Filimonov, Aleksander S.,Chepanova, Arina A.,Luzina, Olga A.,Zakharenko, Alexandra L.,Zakharova, Olga D.,Ilina, Ekaterina S.,Dyrkheeva, Nadezhda S.,Kuprushkin, Maxim S.,Kolotaev, Anton V.,Khachatryan, Derenik S.,Patel, Jinal,Leung, Ivanhoe K.H.,Chand, Raina,Ayine-Tora, Daniel M.,Reynisson, Johannes,Volcho, Konstantin P.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
, (2019/10/28)
Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising therapeutic target in cancer therapy. Combination chemotherapy using Tdp1 inhibitors as a component can potentially improve therapeutic response to many chemotherapeutic regimes. A new set of usnic acid derivatives with hydrazonothiazole pharmacophore moieties were synthesized and evaluated as Tdp1 inhibitors. Most of these compounds were found to be potent inhibitors with IC50 values in the low nanomolar range. The activity of the compounds was verified by binding experiments and supported by molecular modeling. The ability of the most effective inhibitors, used at non-toxic concentrations, to sensitize tumors to the anticancer drug topotecan was also demonstrated. The order of administration of the inhibitor and topotecan on their synergistic effect was studied, suggesting that prior or simultaneous introduction of the inhibitor with topotecan is the most effective.
4-(3-Nitrophenyl)thiazol-2-ylhydrazone derivatives as antioxidants and selective hMAO-B inhibitors: synthesis, biological activity and computational analysis
Secci, Daniela,Carradori, Simone,Petzer, Anél,Guglielmi, Paolo,D’Ascenzio, Melissa,Chimenti, Paola,Bagetta, Donatella,Alcaro, Stefano,Zengin, Gokhan,Petzer, Jacobus P.,Ortuso, Francesco
, p. 597 - 612 (2019/02/14)
A new series of 4-(3-nitrophenyl)thiazol-2-ylhydrazone derivatives were designed, synthesised, and evaluated to assess their inhibitory effect on the human monoamine oxidase (hMAO) A and B isoforms. Different (un)substituted (hetero)aromatic substituents were linked to N1 of the hydrazone in order to establish robust structure–activity relationships. The results of the biological testing demonstrated that the presence of the hydrazothiazole nucleus bearing at C4 a phenyl ring functionalised at the meta position with a nitro group represents an important pharmacophoric feature to obtain selective and reversible human MAO-B inhibition for the treatment of neurodegenerative disorders. In addition, the most potent and selective MAO-B inhibitors were evaluated in silico as potential cholinesterase (AChE/BuChE) inhibitors and in vitro for antioxidant activities. The results obtained from molecular modelling studies provided insight into the multiple interactions and structural requirements for the reported MAO inhibitory properties.
Hydrazinyl arylthiazole based pyridine scaffolds: Synthesis, structural characterization, in?vitro α-glucosidase inhibitory activity, and in silico studies
Ali, Farman,Khan, Khalid Mohammed,Salar, Uzma,Taha, Muhammad,Ismail, Nor Hadiani,Wadood, Abdul,Riaz, Muhammad,Perveen, Shahnaz
, p. 255 - 272 (2017/07/04)
Acarbose, miglitol, and voglibose are the inhibitors of α-glucosidase enzyme and being clinically used for the management of type-II diabetes mellitus. However, many adverse effects are also associated with them. So, the development of new therapeutic agents is an utmost interest in medicinal chemistry research. Current study is based on the identification of new α-glucosidase inhibitors. For that purpose, hydrazinyl arylthiazole based pyridine derivatives 1–39 were synthesized via two step reaction and fully characterized by spectroscopic techniques EI-MS, HREI-MS, 1H-, and 13C NMR. However, stereochemistry of the iminic bond was confirmed by NOESY. All compounds were subjected to in vitro α-glucosidase inhibitory activity and found many folds active (IC50 = 1.40 ± 0.01–236.10 ± 2.20 μM) as compared to the standard acarbose having IC50 value of 856.45 ± 5.60 μM. A limited structure-activity relationship was carried out in order to make a presumption about the substituent's effect on inhibitory activity which predicted that substituents of more negative inductive effect played important role in the activity as compared to the substituents of less negative inductive effect. However, in order to have a good understanding of ligand enzyme interactions, molecular docking study was also conducted. In silico study was confirmed that substituents like halogens (Cl) and nitro (NO2) which have negative inductive effect were found to make important interactions with active site residues.
