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The present research describes the preparation of novel mon-azothiazoles and bis-azothiazoles based on hydrazonoyl halides. These thiazoles are prepared from the reaction of 2-(4-(dimethylamino)benzylidene)hydrazine-1-carbothioamide with α-haloketohydrazonoyl halides in the basic medium (triethylamine) at reflux. The process of preparation is designed and illustrated in the manuscript. The mechanism of the final novel mono- and bis-azothiazoles can be described through thiol group of 2-(4-(dimethylamino)benzylidene)-hydrazine-1-carbothioamide undergo nucleophilic attack to carbon attached to halogen from hydrazonoyl to form S-alkylated intermediate. The intermediate is eliminated hydrogen chloride then at once undergoes intramolecular cycloaddition followed by exclusion of water to provide the novel series of mono- and bis-azothiazole. Structures of the final products were elucidated by FTIR, MS, NMR and elemental analyses. These reactions are provided the desired products in excellent yields. The antiproliferation activity of the newly synthesized compounds was evaluated using the MTT assay against human colorectal adenocarcinoma (DLD-1) and human adenocarcinoma (A549) cells. Furthermore, apoptosis induction was also investigated via the estimation of the caspase-3 levels using western blotting and dual staining technique. [ABSTRACT FROM AUTHOR]

Herein we studied the preparation of different thiazoles via the reaction of 2-(3,4-dimethoxybenzylidene)hydrazine-1-carbothioamide (1) with hydrazonoyl halides under base-catalyzed conditions. The reactions proceed through nucleophilic substitution attack at the halogen atom of the hydrazonoyl halides by the thiol nucleophile to form an S-alkylated intermediate. The latter intermediate undergoes cyclization by the loss of water to afford the final products. The structures of the azo compounds were confirmed by FTIR, MS, NMR, and elemental analyses. Indeed, the newly synthesized azo compounds were estimated for their potential anticancer activities by an MTT assay against different human cancer cells, such as lung adenocarcinoma (A549) and colorectal adenocarcinoma (DLD-1). The caspase-3 levels were also estimated using Western blotting and the dual staining technique to evaluate the potency of the titled compounds to promote apoptosis.

Thiadiazine and thiazoles have attracted importance due to their broad applicability as biologically active compounds. New thiadiazines and thiazoles are prepared via the simple reaction of an α-haloketohydrazonoyl with thiocarbohydrazone derivatives in a basic medium under reflux. A S-alkylated intermediate forms through nucleophile substitution involving the hydrazonoyl halogen and thiocarbohydrazone thiol. In situ cyclization via the condensation between the carbonyl and NH2 or NH moieties of the intermediate forms 1,3,4-thiadiazine and thiazole derivatives, respectively. This method employs inexpensive, commercially available reagents and facile reaction conditions to afford novel thiadiazine/thiazole derivatives in good yields. [ABSTRACT FROM AUTHOR]

The present effort is to use good organized method for the synthesis of novel thiazoles from the reaction of different α-haloketohydrazonoyl halides with thiosemicarbazones in the basic medium at refux. In addition, new polthiazole was prepared from the reaction of 1,4-phenylene-bis(2-oxopropanehydrazonoyl chloride) with 2,2′-(1,4-phenylenebis(methanyl-ylidene))bis(hydrazine-1-carbothioamide) in the presence of basic medium. The formation of the final thiazoles or polythiazole can be explained through nucleophile substitution of the halogen atom form hydrazonoyl halides, followed by removal of water to give the final products as represented in Schemes. The inexpensive, good yielding, simple reaction conditions, and commercial availability of the chemicals make these methods valuable. The description structures for the final compounds are discussed and suggested. New organic substances were elucidated via FTIR, MS, NMR, and elemental analyses. [ABSTRACT FROM AUTHOR]

A series of new amidrazones were prepared by the reaction of [4,4'-bithiazole]-2,2'-diamine with hydrazonoyl chlorides under suitable conditions. The spectral results and the electronic absorption data proved the postulated structures of the resulting compounds. The final compounds are described in the synthetic schemes. The chemical structures of the final products are identified by different techniques, such as mass spectrometry (MS), Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) and elemental analysis. [ABSTRACT FROM AUTHOR]

In this study, new bisthiazoles were efficiently synthesized from the reaction of hydrazine-1,2-bis(carbothioamide) with N-aryl-2-oxopropanehydrazonoyl chlorides or N-aryl C-ethoxycarbonyl methanehydrazonoyl chlorides. The formation of the final compounds starts by nucleophilic attack of thiolates to give S-alkylated intermediate, which in situ undergoes nucleophilic addition and intramolecular cyclization to give the final products as described in the synthetic schemes. The inexpensive and simple reaction conditions, commercial availability of the reagent, good yields and excellent purities of the products make this method valuable from a preparative point of view. Furthermore, the antibacterial activities values of the new compounds were evaluated against Gram-positive and Gram-negative microorganisms. The final products were identified and characterized by elemental analysis, Fourier transforms infrared spectroscopy (FT-IR), mass spectrometry (MS), and nuclear magnetic resonance (NMR). [ABSTRACT FROM AUTHOR]

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, in vitro antiproliferative, and cytotoxicity efficacy of thiazoles and bis-thiazoles were measured., Results: In this work, novel series of 5-methyl-2-(2-(-(6-nitrobenzo[d][1,3]dioxol-5-yl)methylene) hydrazinyl)-4-(aryldiazenyl)thiazoles (4a-f) were prepared via the reaction of hydrazonoyl chlorides 2a-f with 2-((6-nitrobenzo[d][1,3]dioxol-5-yl)methylene)hydrazine-1-carbothioamide (1) in dioxane and employing triethylamine as basic catalyst. Following the same procedure, bisthiazoles (6, 8, and 10) have been synthesized by utilizing bis-hydrazonoyl chlorides (5, 7, and 9) and carbothioamide 1 in a molar ratio (1:2), respectively. The distinctive features in the structure of isolated products were elucidated by spectroscopic tools and elemental analyses. The antioxidant, in vitro anti-proliferative, cytotoxicity, and anti-cancer efficacy of thiazoles and bis-thiazoles were evaluated. Compounds 4d and 4f were the most potent antioxidant agents. Gene expression of apoptosis markers and fragmentation assay of DNA were assessed to explore the biochemical mechanism of synthesized products. Thiazoles significantly inhibited cell growth and proliferation more than bis-thiazoles. They induced apoptosis through induction of apoptotic gene expression P53 and downregulation of antiapoptotic gene expression Bcl-2. Moreover, they induced fragmentation of DNA in cancer cells, indicating that they could be employed as anticancer agents by inhibiting tumor growth and progression and can be considered effective compounds in the strategy of anti-cancer agents' discovery., Conclusion: Synthesis, DPPH Radical Scavenging, Cytotoxic activity, and Apoptosis Induction Efficacy based on Novel Thiazoles and Bis-thiazoles., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds to afford new pyrazoles containing thiadiazole compounds. The new synthesized compounds were identified by elemental analysis and various spectral data (Fourier transform infrared spectroscopy, mass spectrometry, ¹H and 13C nuclear magnetic resonance). [ABSTRACT FROM AUTHOR]

Small heterocyclic compounds containing nitrogen and sulfur atoms, such as thiazole derivatives, represent a significant class of organic azoles that exhibit promising bioactivities and have a great potential in medicinal and agricultural fields. A convenient and high-yielding synthetic approach for a range of organic molecules is presented. The nuclease-like activities of compounds were studied with the aid of E. coli AB1157 DNA and agarose gel electrophoresis. The antioxidant evaluation of the compounds was carried out with different antioxidant techniques, such as ABTS and NO scavenging efficiency. The antibacterial behavior was evaluated against various bacterial strains, both Gram-positive and -negative, and the minimum inhibitory concentration (MIC) values of these compounds were determined. The antiproliferative activities and IC50 values of the synthesized organic molecules compounds against HEPG-2, MCF-7, and HCT-116 cell lines were evaluated.

Synthesis and characterization of new thiadiazoles, bisthiadiazoles from the reaction of mono- and di-hydrazonoyl halides with various hydrazinecarbodithioate derivatives were studied. Treatment of hydrazonoyl halides with 2,5-dihydrazinyl-1,3,4-thiadiazole afforded new bistriazines containing thiadiazole; we also examined the reaction of 2,5-dihydrazinyl-1,3,4-thiadiazole with active methylene compounds to afford new pyrazoles containing thiadiazole compounds. The new synthesized compounds were identified by elemental analysis and various spectral data (Fourier transform infrared spectroscopy, mass spectrometry, 1H and 13C nuclear magnetic resonance).

The present work describes the preparation of new thiadiazoles through a simple intramolecular reaction of mono- and bis-hydrazonoyl halides with methyl hydrogen phenyl carbonimidodithioate or methyl-2-arylidene hydrazinecarbodithioate. The synthetic method involves nucleophilic substitution followed by intramolecular cyclization reactions mediated by evolution of methanethiol. The structures of the title compounds were elucidated by elemental analyses, and FTIR, MS and NMR spectra. [ABSTRACT FROM AUTHOR]

Herein we studied the preparation of different thiazoles via the reaction of 2-(3,4-dimethoxybenzylidene)hydrazine-1-carbothioamide ( 1 ) with hydrazonoyl halides under base-catalyzed conditions. The reactions proceed through nucleophilic substitution attack at the halogen atom of the hydrazonoyl halides by the thiol nucleophile to form an S -alkylated intermediate. The latter intermediate undergoes cyclization by the loss of water to afford the final products. The structures of the azo compounds were confirmed by FTIR, MS, NMR, and elemental analyses. Indeed, the newly synthesized azo compounds were estimated for their potential anticancer activities by an MTT assay against different human cancer cells, such as lung adenocarcinoma (A549) and colorectal adenocarcinoma (DLD-1). The caspase-3 levels were also estimated using Western blotting and the dual staining technique to evaluate the potency of the titled compounds to promote apoptosis.

Background: Hydrazonoyl halides are convenient for the synthesis of arylazothiazoles., Materials and Methods: A series of novel arylazothiazoles were efficiently synthesized from the reaction of hydrazonoyl chlorides with 2-(adamantan-2-ylidene)hydrazinecarbothioamide or 2-(ferrocenyl-1-ylidene)hydrazinecarbo-- thioamide in dioxane used as an aprotic solvent because of its lower toxicity and higher boiling point (101 °C) and triethylamine at reflux. The reaction mechanistic pathway proceeded by the nucleophilic substitution reaction by the elimination of hydrogen chloride to give thiohydrazonates as intermediate, which in situ undergo intramolecular cyclization and loss of water molecule to afford the final product of novel arylazothiazoles. This method is simple with good yield and excellent purities., Results and Discussion: The synthetic schemes for the final products are proposed and discussed. The chemical structures of the final products were identified by different techniques, such as elemental analysis, Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS)., Conclusion: In this article, we prepared arylazothiazoles from the reaction of 2-(adamantan-2-ylidene)hydrazinecarbothioamide or 2-(ferrocenyl-1-ylidene)hydrazinecarbothioamide with hydrazonoyl halides., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

Background: Approximately, 5-7 million people are infected with T. cruzi in the world, and approximately 10,000 people per year die of complications linked to this disease., Methods: This work describes the construction of a new family of hidrazonoyl substituted derivatives, structurally designed exploring the molecular hybridization between megazol and nitrofurazone., Results and Discussion: The compounds were evaluated for their in vitro activity against bloodstream trypomastigotes of Trypanosoma cruzi, etiological agent of Chagas disease, and for their potential toxicity to mammalian cells., Conclusion: Among these hydrazonoyl derivatives, we identified the derivative (4) that showed trypanocidal activity (IC50/24 h = 15.0 µM) similar to Bz, the standard drug, and low toxicity to mammalian cells, reaching an SI value of 18.7., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

Small heterocyclic compounds containing nitrogen and sulfur atoms, such as thiazole derivatives, represent a significant class of organic azoles that exhibit promising bioactivities and have a great potential in medicinal and agricultural fields. A convenient and high-yielding synthetic approach for a range of organic molecules is presented. The nuclease-like activities of compounds were studied with the aid of E. coli AB1157 DNA and agarose gel electrophoresis. The antioxidant evaluation of the compounds was carried out with different antioxidant techniques, such as ABTS and NO scavenging efficiency. The antibacterial behavior was evaluated against various bacterial strains, both Gram-positive and -negative, and the minimum inhibitory concentration (MIC) values of these compounds were determined. The antiproliferative activities and IC50 values of the synthesized organic molecules compounds against HEPG-2, MCF-7, and HCT-116 cell lines were evaluated. [ABSTRACT FROM AUTHOR]