Green Efficient Synthesis of [1,3,4]Thiadiazole-Tethered Alkoxyaryl Hydrazones: Evaluation of Antitumor Activities and Molecular Docking Studies.

Hydrazono-[1,3,4]-thiadiazoles have a prominent position among the heterocyclic compounds due to their broadening aspects of biological activities. In the current study, a neoteric series of [1,3,4]-thiadiazoles tethered to alkoxyaryl hydrazone has been formulated via the treatment of methyl 2-[3-(pentyloxy)-benzylidene]-hydrazine-1-carbodithioate and hydrazonoyl chlorides in ethanolic solution under thermal conditions. DABCO, as an environmentally nontoxic material, was utilized as a superior basic catalyst for the latter reaction.

Insights on Regioselective Synthesis of Fused Thiazoles: Density Functional Theory Calculations, Local Reactivity Indices, and Molecular Electrostatic Potential Analysis.

A regioselective protocol is developed and validated for the synthesis of pyrazolo[3,4-d]thiazoles and polycyclic-fused thiazoles through the reactions of 2-[((E)-benzylidene)hydrazono]-5-[(Z)-4-methoxybenzylidene]thiazolidin-4-one with hydrazine derivatives or heterocyclic amines, respectively. The products are confirmed by spectral and elemental analyses. Density functional theory studies, including frontier molecular orbital analysis, local reactivity indices, and molecular electrostatic potential mapping, explain the observed regioselectivity and support a proposed reaction mechanism.

Synthesis, Molecular Characterization, and Antimicrobial Evaluation of Hydrazones Derived from 2-Hydrazinobenzimidazole.

Introduction: Hydrazones, due to the structural diversity of their nitrogen atoms, possess both electrophilic and nucleophilic properties, enabling strong hydrogen bonding interactions with enzymes and receptors. This study aimed to synthesize novel hydrazone derivatives and evaluate their antimicrobial potential.

Methods: Hydrazones were synthesized via condensation of 2-hydrazinobenzimidazole with various aldehydes or ketones using citric acid as an eco-friendly catalyst.

Eco-synthesis route: Developing bis-hydrazono[1,2,4]-thiadiazoles via a green synthetic approach with calcium oxide-chitosan nanocomposite.

Modern environmental organic chemistry is focused on developing cost-efficient, versatile, environmentally acceptable catalytic chemicals that are also highly effective. Herein, hybrid calcium-chitosan nanocomposite films was prepared by doping calcium oxide molecules into a chitosan matrix at weight percentage (15, 20, and 25 % wt. chitosan‑calcium) using an easy and affordable simple co-precipitation process.

Synthesis of Bis-thiazoles Tethered 1,4-Dihydropyridine and Pyridine Linkers Simple Oxidation and their Molecular Docking as VEGFR -TK Inhibitors.

Aim: In this study, a neoteric and expedient oxidation method is applied for a variety of Hantzsch 1,4-dihydropyridine derivatives such as 1,4-dihydro- 2,6-dimethyl-3,5-diacetylpyridine, 3,5-bis-hydrazono--2,6-dimethyl-1,4-dihydropyridine, and 3,5-bis-thiazoly-2,6-dimethyl-1,4-dihydro pyridines.

Methods: This simple oxidation is based upon the generation of nitrous acid from an aqueous sodium nitrite and acetic acid mixture and could be used to downgrade costs, sustain resources, and minimize chemical wastes. Also, a molecular modeling strategy was used to study the mechanism of action for various derivatives of bis-hydrazinylidene- thiazole as the protein Vascular Endothelial Growth Factor Receptor Tyrosine Kinase (VEGFR TK) inhibitor through evaluating their binding scores and modes compared with Sorafenib as a reference standard.

A Literature Review Focusing on the Antiviral Activity of [1,2,4] and [1,2,3]-triazoles.

Out of a variety of heterocycles, triazole scaffolds have been shown to play a significant part in a wide array of biological functions. Many drug compounds containing a triazole moiety with important antimicrobial, anticancer and antidepressant properties have been commercialized. In addition, the triazole scaffold exhibits remarkable antiviral activity either incorporated into nucleoside analogs or non-nucleosides.

Synthesis, DPPH Radical Scavenging, Cytotoxic Activity, and Apoptosis Induction Efficacy of Novel Thiazoles and Bis-thiazoles.

Background: Heterocyclic materials-containing thiazoles exhibited incredible importance in pharmaceutical chemistry and drug design due to their extensive biological properties.

Methods: Synthesis of thiazoles and bis-thiazoles from the reaction of 2-((6-Nitrobenzo[ d][1,3]dioxol-5-yl)methylene)hydrazine-1-carbothioamide with hydrazonoyl chlorides in dioxane and in the existence of triethylamine as basic catalyst. The antioxidant, antiproliferative, and cytotoxicity efficacy of thiazoles and bis-thiazoles were measured.

Green Synthetic Approaches of 2-Hydrazonothiazol-4(5)-ones Using Sustainable Barium Oxide-Chitosan Nanocomposite Catalyst.

The diverse applications of metal oxide-biopolymer matrix as a nanocomposite heterogenous catalyst have caused many researches to scrutinize the potential of this framework. In this study, a novel hybrid barium oxide-chitosan nanocomposite was synthesized through a facile and cost-effective co-precipitation method by doping barium oxide nanoparticles within the chitosan matrix at a weight percentage of 20 wt.% BaO-chitosan.

Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents.

A novel set of thiazolylhydrazonothiazoles bearing an indole moiety were synthesized by subjection reactions of carbothioamide derivative and hydrazonoyl chlorides (or α-haloketones). The cytotoxicity of the synthesized compounds was evaluated against the colon carcinoma cell line (HCT-116), liver carcinoma cell line (HepG2), and breast carcinoma cell line (MDA-MB-231), and demonstrated encouraging activity. Furthermore, when representative products were assessed for toxicity against normal cells, minimal toxic effects were observed, indicating their potential safety for use in pharmacological studies.

Synthesis and In Silico Study of Some New -[1,3,4]thiadiazolimines and -Thiazolimines as Potential Inhibitors for SARS-CoV-2 Main Protease.

A novel series of -[1,3,4]thiadiazolimines, and -thiazolimines, with alkyl linker, were synthesized through general routes from cyclization of 1,1'-(hexane-1,6-diyl)bis(3-phenylthiourea) and hydrazonoyl halides or -haloketones, respectively. Docking studies were applied to test the binding affinity of the synthesized products against the M of SARS-CoV-2. The best compound, , has average binding energy (-7.

Chitosan-Strontium Oxide Nanocomposite: Preparation, Characterization, and Catalytic Potency in Thiadiazoles Synthesis.

Recently, Strontium oxide (SrO) nanoparticles (NPs) and hybrids outperformed older commercial catalysts in terms of catalytic performance. Herein, we present a microwave-assisted easy in situ solution casting approach for the manufacture of strontium oxide nanoparticles doped within a naturally occurring polymer, chitosan (CS), at varying weight percentages (2.5, 5, 10, 15, and 20 wt.

Synthesis, Molecular Docking Study, and Cytotoxic Activity against MCF Cells of New Thiazole-Thiophene Scaffolds.

Investigating novel compounds that may be useful in designing new, less toxic, selective, and potent breast anticancer agents is still the main challenge for medicinal chemists. Thus, in the present work, acetylthiophene was used as a building block to synthesize a novel series of thiazole-bearing thiophene derivatives. The structures of the synthesized compounds were elucidated based on elemental analysis and spectral measurements.

Synthesis and greener pastures biological study of bis-thiadiazoles as potential Covid-19 drug candidates.

A novel series of bis- (Abdelhamid et al., 2017, Banerjee et al., 2018, Bharanidharan et al.

Bio-Based (Chitosan-ZnO) Nanocomposite: Synthesis, Characterization, and Its Use as Recyclable, Ecofriendly Biocatalyst for Synthesis of Thiazoles Tethered Azo Groups.

In recent years, nanotechnology has become a considerable research interest in the area of preparation of nanocatalysts based on naturally occurring polysaccharides. Chitosan (CS), as a naturally occurring biodegradable and biocompatible polysaccharide, is successfully utilized as an ideal template for the immobilization of metal oxide nanoparticles. In this study, zinc oxide nanoparticles have been doped within a chitosan matrix at dissimilar weight percentages (5, 10, 15, 20, and 25 wt.

Potential COVID-19 Drug Candidates Based on Diazinyl-Thiazol-Imine Moieties: Synthesis and Greener Pastures Biological Study.

A novel series of 1-aryl--[4-phenyl-5-(arylazo)thiazol-2-yl)methanimines has been synthesized via the condensation of 2-amino-4-phenyl-5-arylazothiazole with various aromatic aldehydes. The synthesized imines were characterized by spectroscopic techniques, namely H and C-NMR, FTIR, MS, and Elemental Analysis. A molecular comparative docking study for was calculated, with reference to two approved drugs, Molnupiravir and Remdesivir, using 7BQY (M; PDB code 7BQY; resolution: 1.

Synthesis of Chitosan-LaO Nanocomposite and Its Utility as a Powerful Catalyst in the Synthesis of Pyridines and Pyrazoles.

Recently, the development of nanocatalysts based on naturally occurring polysaccharides has received a lot of attention. Chitosan (CS), as a biodegradable and biocompatible polysaccharide, is considered to be an excellent template for the design of a hybrid biopolymer-based metal oxide nanocomposite. In this case, lanthanum oxide nanoparticles doped with chitosan at different weight percentages (5, 10, 15, and 20 wt% CS/LaO) were prepared via a simple solution casting method.

Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (M).

A novel series of some hydrazones bearing thiazole moiety were generated via solvent-drop grinding of thiazole carbohydrazide with various carbonyl compounds. Also, dehydrative-cyclocondensation of with active methylene compounds or anhydrides gave the respective pyarzole or pyrazine derivatives. The structures of the newly synthesized compounds were established based on spectroscopic evidences and their alternative syntheses.

Two decades of the synthesis of mono- and bis-aminomercapto[1,2,4]triazoles.

4-Amino-5-mercapto[1,2,4]triazole and its 3-substituted derivatives have proven to be of biological interest and provide access to a new class of biologically active heterocyclic compounds for biomedical applications. This study will be helpful for scientific researchers interested in the chemistry of bifunctional versatile compounds as it provides a collection of all the methods for the preparation of 3-substituted-4-amino-5-mercapto[1,2,4]triazoles with aliphatic, aromatic, and heterocyclic moieties during the period from 2000 to mid-2020.

Synthesis, characterization and application of copper oxide chitosan nanocomposite for green regioselective synthesis of [1,2,3]triazoles.

Chitosan copper (II) oxide nanocomposite was synthesized, characterized and used to synthesize [1,2,3]triazoles. Nanocomposite was characterized by using FTIR, XRD, FESEM, and EDS techniques, which reflected rough morphology. The powerful catalytic activity of hybrid nanocomposite was utilized to synthesize chalcones (3a-p) in relatively high yields (82%-98%) and multicomponent regio-selective cycloaddition of chalones, aryl halides (4), and sodium azide to afford the expected N-2-aryl[1,2,3]triazoles (5a-h) (80%-95% yield) rather than N-1-aryl[1,2,3]-triazoles (6a-h).

Chitosan-MgO Nanocomposite: One Pot Preparation and Its Utility as an Ecofriendly Biocatalyst in the Synthesis of Thiazoles and [1,3,4]thiadiazoles.

A chitosan-MgO hybrid nanocomposite was prepared using a simple chemical precipitation method and characterized using Fourier transform spectroscopy (FTIR), elemental analysis (EDX), and scanning electron microscopy (SEM). The nanocomposite was served as a powerful ecofriendly basic catalyst under microwave irradiation in the synthesis of two novel series of 5-arylazo-2-hydrazonothiazoles ⁻ and 2-hydrazono[1,3,4]thiadiazoles ⁻, incorporating a sulfonamide group. The structures of the synthesized products were elucidated by spectral data and elemental analyses.

Synthesis, Biological Evaluation, and Molecular Docking of Novel Thiazoles and [1,3,4]Thiadiazoles Incorporating Sulfonamide Group as DHFR Inhibitors.

2-(1-{4-[(4-Methylphenyl)sulfonamido]phenyl}ethylidene)thiosemicarbazide (3) was exploited as a starting material for the synthesis of two novel series of 5-arylazo-2-hydrazonothiazoles 6a - 6j and 2-hydrazono[1,3,4]thiadiazoles 10a - 10d, incorporating sulfonamide group, through its reactions with appropriate hydrazonoyl halides. The structures of the newly synthesized products were confirmed by spectral and elemental analyses. Also, the antimicrobial, anticancer, and DHFR inhibition potency for two series of thiazoles and [1,3,4]thiadiazoles were evaluated and explained by molecular docking studies and SAR analysis.

Synthesis of New Bis-Spiropyrazoles as Antitumor Agents under Ultrasound Irradiation.

Objective And Background: Hydrazonoyl halides were used as precursors for the synthesis of a new series of bis-spiropyrazoles via reaction with 3,5-diarylidene-piperidone derivatives under ultrasound irradiation. The products were secluded in good yield after short reaction periods.

Conclusion: The anticancer activity of bis-spiropyrazoles against HepG2 (hepatic cancer), A549 (lung cancer) and CaCo2 (colon cancer) cell lines was screened.

Rational design, synthesis, pharmacophore modeling, and docking studies for identification of novel potent DNA-PK inhibitors.

Drugs of cancer based upon ionizing radiation or chemotherapeutic treatment may affect breaking of DNA double strand in cell. DNA-PK enzyme has emerged as an attractive target for drug discovery efforts toward DNA repair pathways. Hence, the search for potent and selective DNA-PK inhibitors has particularly considered state-of-the art and several series of inhibitors have been designed.

Azoles and bis-azoles: synthesis and biological evaluation as antimicrobial and anti-cancer agents.

Novel hydrazonoyl halides 3, 5 and bis-hydrazonoyl halides 7, 9 were synthesized. The synthetic utility of bis-hydrazonoyl halide 7 was explored to prepare novel bis-azole 13 with antipyrine moiety. On the other hand, [1,3,4]thiadiazol-2(3H)-ylidene 17 and thiazol-2(3H)-ylidene 21 derivatives, with antipyrine moiety, were prepared from the reaction of 3-mercapto-3-(phenylamino)acrylamide derivative 10 with N-phenyl benzenecarbohydrazonoyl chloride (14) and 3-(2-bromoacetyl)-2H-chromen-2-one (18), respectively.

Synthesis under microwave irradiation of [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles and other diazoles bearing indole moieties and their antimicrobial evaluation.

Microwave-assisted synthesis of some novel compounds, namely, 3-(2-methyl-1H-indol-3-yl)-6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 5a,b was accomplished via bromination of 2-methyl-3-[4-(arylideneamino)-5-mercapto-4H-[1,2,4]triazol-3-yl]-1H-indoles 3a,b. Also, new [1,3,4]thiadiazoles 12a,b, [1,2,4]triazoles 15a,b and [1,3,4]oxadiazoles 19a,b, with indole moieties, were prepared by cyclization of 1-[(2-methyl-1H-indole)-3-carbonyl]thiosemicarbazides 8a,b under microwave irradiation using different reaction conditions. Moreover, reaction of acid hydrazide 7 with ethyl 2-(N-phenylhydrazono)-3-oxobutanoate (20) gave the respective phenylhydrazonopyrazole derivative 21 under the reaction conditions employed.