947527-72-2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 79-19-6 thiosemicarbazide 
• 4346-94-5 thiosemicarbazide hydrochloride 

Downstream Products

• 1004980-99-7 C₁₅H₁₃N₅O₃S 
• 59565-53-6 5-(4-hydroxy phenyl)-1,3,4-thiadiazole-2-amine 
• 1489265-05-5 ethyl 2-[(E)-2-[(4-hydroxyphenyl) methylidene] hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of N-oxide derivatives with potent in vivo antileishmanial activity

Leishmaniasis is a neglected disease that affects 12 million people living mainly in developing countries. Herein, 24 new N-oxide-containing compounds were synthesized followed by in vitro and in vivo evaluation of their antileishmanial activity. Compound 4f, a furoxan derivative, was particularly remarkable in this regard, with EC50 value of 3.6 μM against L. infantum amastigote forms and CC50 value superior to 500 μM against murine peritoneal macrophages. In vitro studies suggested that 4f may act by a dual effect, by releasing nitric oxide after biotransformation and by inhibiting cysteine protease CPB (IC50: 4.5 μM). In vivo studies using an acute model of infection showed that compound 4f at 7.7 mg/Kg reduced ~90% of parasite burden in the liver and spleen of L. infantum-infected BALB/c mice. Altogether, these outcomes highlight furoxan 4f as a promising compound for further evaluation as an antileishmanial agent.

Efficient reduction of graphene oxide to graphene nanosheets using a silica-based ionic liquid: Synthesis, characterization and catalytic properties of IMD-Si/FeCl4-@GNS

The aim of the present protocol is to develop a facile route for the synthesis of novel ionic liquid (IL)-functionalized graphene nano sheets (IMD-Si/FeCl4-@GNS). An imidazolium IL with tetrachloroferrate as an anion (IMD-Si/FeCl4-) was used to reduce graphene oxide. IMD-Si/FeCl4-@GNS were well characterized using various techniques such as Fourier transform infrared (FTIR), Raman, ultraviolet-visible diffuse reflectance spectroscopy (UV-VIS DRS), scanning electron microscopy/energy dispersive X-ray (SEM/EDX), elemental mapping, transmission electron microscopy (TEM), powder X-ray diffraction (XRD), thermal gravimetry (TG), electron paramagnetic resonance (EPR), and X-ray photoelectron spectroscopy (XPS) analyses. The IL-functionalized material was investigated for its catalytic properties and found to be an efficient catalyst for the synthesis of (E)-selective substituted thiosemicarbazone derivatives. The (E)-selectivity was confirmed using DFT calculations which showed that the (E)-isomer was stabilized by 4.90 kcal mol-1 more than the (Z)-isomer. The catalyst maintained its catalytic activity for six successive runs.

Novel tyrosyl-DNA phosphodiesterase 1 inhibitors enhance the therapeutic impact of topoteсan on in vivo tumor models

The druggability of the tyrosyl-DNA phosphodiesterase 1 (Tdp1) enzyme was investigated in conjunction with topoisomerase 1 inhibition. A novel class of thiazole, aminothiazole and hydrazonothiazole usnic acid derivatives was synthesized and evaluated as Tdp1 inhibitors and their ability to sensitize tumors to topotecan, a topoisomerase inhibitor in clinical use. Of all the compounds tested, four hydrazinothiazole derivatives, 20c, 20d, 20h and 20i, inhibited the enzyme in the nanomolar range. The activity of the compounds was verified by affinity experiments as well as supported by molecular modelling. The most effective Tdp1 inhibitor, 20d, was ton-toxic and increased the effect of topotecan both in vitro and in vivo in the Lewis lung carcinoma model. Furthermore, 20d showed significant increase in the antitumor and antimetastatic effect of topotecan in mice. The results presented here justify compound 20d to be considered as a drug lead for antitumor therapy.

Selected aryl thiosemicarbazones as a new class of multi-targeted monoamine oxidase inhibitors

A series of 13 phenyl substituted thiosemicarbazones (SB1-SB13) were synthesized and evaluated for their inhibitory potential towards human recombinant monoamine oxidase A and B (MAO-A and MAO-B, respectively) and acetylcholinesterase. The solid state structure of SB4 was ascertained by the single X-ray diffraction technique. Compounds SB5 and SB11 were potent for MAO-A (IC50 1.82 ± 0.14) and MAO-B (IC50 0.27 ± 0.015 μM), respectively. Furthermore, SB11 showed a high selectivity index (SI > 37.0) for MAO-B. The effects of fluorine orientation revealed that SB11 (m-fluorine) showed 28.2 times higher inhibitory activity than SB12 (o-fluorine) against MAO-B. Furthermore, inhibitions by SB5 and SB11 against MAO-A and MAO-B, respectively, were recovered to near reference levels in reversibility experiments. Both SB5 and SB11 showed competitive inhibition modes, with Ki values of 0.97 ± 0.042 and 0.12 ± 0.006 μM, respectively. These results indicate that SB5 and SB11 are selective, reversible and competitive inhibitors of MAO-A and MAO-B, respectively. Compounds SB5, SB7 and SB11 showed moderate inhibition against acetylcholinesterase with IC50 values of 35.35 ± 0.47, 15.61 ± 0.057 and 26.61 ± 0.338 μM, respectively. Blood-brain barrier (BBB) permeation was studied using the parallel artificial membrane permeation assay (PAMPA) method. Molecular docking studies were carried out using AutoDock 4.2.

Aryl thiosemicarbazones for the treatment of trypanosomatidic infections

Basing on a library of thiadiazole derivatives showing anti-trypanosomatidic activity, we have considered the thiadiazoles opened forms and reaction intermediates, thiosemicarbazones, as compounds of interest for phenotypic screening against Trypanosoma b

Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents

4-Thiazolidinone analogs 1-20 were synthesized, characterized by 1H NMR and EI-MS and investigated for urease inhibitory activity. All twenty (20) analogs exhibited varied degree of urease inhibitory potential with IC50 values 1.73-69.65 μM, if compared with standard thiourea having IC50 value of 21.25 ± 0.15 μM. Among the series, eight derivatives 3, 6, 8, 10, 15, 17, 19, and 20 showed outstanding urease inhibitory potential with IC50 values of 9.34 ± 0.02, 14.62 ± 0.03, 8.43 ± 0.01, 7.3 ± 0.04, 2.31 ± 0.002, 5.75 ± 0.003, 8.81 ± 0.005, and 1.73 ± 0.001 μM, respectively, which is better than the standard thiourea. The remaining analogs showed good to excellent urease inhibition. The binding interactions of these compounds were confirmed through molecular docking studies.

Synthesis, characterization, cytotoxicity and antimycobacterial screening of Some p-substituted benzyl thiosemicarbazones

The aim of present study is to synthesize a series of different p-substituted benzyl thiosemicarbazone and evaluate their cytotoxicity as well as their antimycobacterial activity. The chemical structures have been assigned by micro analysis and spectral d

Platinum(II) and palladium(II) aryl-thiosemicarbazone complexes: Synthesis, characterization, molecular modeling, cytotoxicity, and antimicrobial activity

Platinum(II) and palladium(II) complexes [ML2] have been isolated from reaction of K2PtCl4 or K 2PdCl4 and ligands (L) derived from thiosemicarbazones. The complexes were characterized by elemental analysis, Raman, IR, and NMR spectroscopy. In addition, quantum mechanical calculations were used to predict their structures and spectroscopic properties. For the first time, theoretical calculations using 195Pt NMR data were used to support the suggested structures. The results indicate that the thionic sulfur and the azomethine nitrogen are bonded to the metal ion in a trans configuration. Antibacterial activities and cytotoxicities of the complexes to B16-F10 and CT26.WT cell lines were also investigated. Some of the complexes demonstrated superior cytotoxic activity compared to cisplatin. 2014

Synthesis, NMR structural characterization and molecular modeling of substituted thiosemicarbazones and semicarbazones using DFT calculations to prove the syn/anti isomer formation

Thiosemicarbazones possessing electron-donating and electron-withdrawing groups were prepared, and their spectral characteristics determined. In all cases, the spectra showed that one isomer was formed, allowing further functionalization to molecules of biological interest. We provide NMR data for some of the thiosemicarbazones and semicarbazones. We also provide evidence that for 2-pyridyl thiosemicarbazone, the syn isomer slowly converts into the anti isomer in dimethyl sulfoxide solvent with first-order kinetics. Molecular modeling and density functional theory calculations confirmed these observations. Copyright

2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H37Rv, by in vitro assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene] hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2-[(E)-2-[(2- hydroxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 μM and 25 μM respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with β-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 μM and 0.177 μM respectively.