Synthesis Of Novel Heterocyclic System Research Articles

A convenient one-pot synthesis of novel heterocyclic systems of 9-chloro-4-methyl-6,11-dihydro-5H-benzo[b]pyrimido[4,5-e][1,4]diazepine and inhibitory evaluation against bromodomain-containing protein 4 (BRD4) enzyme by molecular docking

A convenient one-pot synthesis of novel heterocyclic systems of 9-chloro-4-methyl-6,11-dihydro-5H-benzo[b]pyrimido[4,5-e][1,4]diazepine and inhibitory evaluation against bromodomain-containing protein 4 (BRD4) enzyme by molecular docking

Recent trends in synthetic strategies using magnetic nanostructures as green catalysts in synthesis of pyran analogues

In recent years, magnetic nanoparticles and nanocomposites play an important role as a nanocatalyst in the creation of a wide range of bioactive heterocycles with extraordinarily high activity and selectivity, low energy consumption, and extended life. Among all heterocycles, many natural products, pharmaceuticals, and bioactive compounds contain pyran scaffolds which have a wide range of uses in biomedical research, industry, and medicine. Additionally, these are also widely used in the synthesis of novel heterocyclic systems as precursors. This study focused on recent advances in the last 5 years in using various magnetic recoverable and recycled nanoparticles and nanocomposites to synthesize pyran derivatives and their pharmacological activity. This article has been classified into three subsections: (i) MNPs‐metal nanocomposite catalyzed reactions, (ii) MNPs‐organic based nanocomposite catalyzed reactions, and (iii) MNPs‐ionic liquid nanocomposite catalyzed reactions and (iv) MNPs‐acid based nanocomposite to describe catalytic efficiency of magnetic nanocomposites for the synthesis of pyran derivatives. A comparative study of nanocomposites and different approaches for green synthesis of pyrans by highlighting the advantages and disadvantages along with catalyst recovery and recyclability has been mentioned, which will help scientists to probe and stimulate the study of these scaffolds.

An Efficient One-Pot and Regioselective Synthesis of Novel Heterocyclic Systems of 5,6-Dihydrobenzo[b]Pyrimido[5,4-f][1,4]Oxazepine

An efficient and convenient one-pot two-step process for the regioselective synthesis of the novel tricyclic system 2-chloro-4-methyl-5,6-dihydrobenzo[b]pyrimido[5,4-f][1,4] oxazepine has been described via heterocyclization of 5-(chloromethyl)-2,4-dichloro-6-methylpyrimidine and 2-aminophenol under mild condition followed by reaction with the various secondary amine in moderate to good yields and short time (4a-f).

An efficient synthesis of novel heterocyclic systems incorporating coumarin moiety

AbstractPolyfunctional 3‐chloro‐3‐(4‐chlorocoumarin‐3‐yl)prop‐2‐enal (1) used as a precursor for heterocyclic synthesis. Dichloro‐aldehyde 1 was allowed to react with variable nucleophilic reagents, and a diversity of heterocyclic systems linked coumarin moiety at position 3 was synthesized. The reaction of compound 1 with guanidine and cyanoguanidine produced 3‐(pyrimidin‐4‐yl)‐4‐chlorocoumarins 2 and 3. Treating compound 1 with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole yielded triazolo[4,3‐a]pyrimidine 4 and pyrimido[1,2‐a]benzimidazole 5. The treatment of compound 1 with cyanoacetamide, N‐benzyl‐2‐cyanoacetamide, and 1H‐benzimidazolylacetonitrile gave 2(1H)‐pyridones 6, 7 and pyrido[1,2‐a]benzimidazole 8. The reaction of compound 1 with 5‐amino‐3‐methyl‐1H‐pyrazole and 6‐aminouracil afforded pyrazolo[3,4‐b]pyridine 9 and pyrido[2,3‐d]pyrimidine 10, respectively. Compound 1 reacted with ethylenediamine, o‐phenylenediamine, o‐aminophenol, and o‐aminothiophenol leading to 5‐(imidazolylmethyl)chromeno[4,3‐e] [1,4]diazepine (12), 3‐(benzodiazepin/benzoxazepin‐2‐yl)‐4‐chlorocoumarins 13, 14, and 6‐(benzothiazol‐2‐ylmethyl)chromeno[4,3‐b][1,5]benzothiazepine 16, respectively. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.

Utility of Lauroyl Isothiocyanate as a Scaffold in the Synthesis of Some Novel Pyrimidine Derivatives and Their Antimicrobial Assessment.

The reaction of lauroyl isothiocyanate 1 with enaminonitrile derivative 2 furnished N-(6-cyano-3, 4-diphenylthieno[2,3-c]pyridazin-5-yl-carbamothioyl)dodecanamide 3, which was used as precursor for the synthesis of novel heterocyclic systems. Polyfunctional pyrimidine and fused pyrimidine derivatives were obtained by the cyclization of compound 3 under different basic conditions as well as its reactions with thiourea, o-aminothiophenol, hydrazine hydrate, phenyl hydrazine, ethyl phenyl acetate or ethyl benzoyl acetate. The structures of the new compounds were confirmed by microanalytical and spectral properties. The synthesised compounds were tested in-vitro for their antimicrobial activity and showed congruent results against most of the tested microorganisms compared to the standard drugs Gentamycin and Ketoconazol.

Oximes of Nucleosides and Related Compounds: Synthesis, Reactions and Biological Activity

Background: Literature data on the synthesis and structure of oximes of nucleosides and related nitrogenous bases from pyrimidine and purine were reviewed. Synthesis of novel heterocyclic systems from nucleoside oximes related pyrimidine oximes was described. The biological activity of derivatives of nucleoside and nitrogenous base oximes was also reviewed. <p> Objective: The review focuses on the recent progress in the area of nucleoside oxime synthesis, reactions and biological activity. Conclusion: In summary, literature data on the synthesis and structure of oximes of nucleosides and related nitrogenous bases derived from pyrimidine, which play an important role in the biological processes, were reviewed. Synthesis of novel heterocyclic systems from nucleoside oximes related pyrimidine oximes was described. The biological activity of derivatives of nucleoside and nucleotide oximes was also reviewed. The studied class of compounds show a wide range of imino-amino and imino-nitroso tautomerism, which was investigated in the presented literature by 1H, 13C and 15N NMR spectroscopy methods. Also, according to the authors point of view, due to imino-amino and/or imino-nitroso tautomerism the nucleoside oximes show interesting activity. Most of the compounds exhibit biological activity characteristic of not only oxime derivatives, but also activity of hydroxylamines or nitroso compounds.

Novel thiazolo[3,2-b]-1,2,4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: Synthesis, biological evaluation and molecular modeling studies

3-Substituted-1,2,4-triazole-5-thiones are versatile synthetic intermediates for the preparation of several biologically active N-bridged heterocyclic compounds, given that they have two reactive sites, thiocarbonyl and an amine nitrogen (N1/N4). For several years, our interest has focused on the synthesis of novel heterocyclic systems derived from 3-substituted-1,2,4-triazole-5-thiones having analgesic/anti-inflammatory activity. In this study, a series of novel thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one derivatives bearing naproxen was synthesized and evaluated for their in vivo analgesic and anti-inflammatory properties in acute experimental pain and inflammation models. The compounds were also tested for their ulcerogenic potential. Our findings showed that all the newly synthesized derivatives attenuate nociception and inflammation compared with a control. All the synthesized compounds exhibited much lower ulcerogenic risk than the standard drugs indomethacin and naproxen. Some compounds with significant analgesic and/or anti-inflammatory activities as well as low ulcer scores were further evaluated for in vitro COX-1 and COX-2 inhibitory potential in a COX-catalyzed prostaglandin biosynthesis assay. Among the tested compounds, compound 1q showed the highest selectivity index (SI) of 4.87. The binding mode for some of the tested compounds to the cyclooxygenase (COX) enzymes was predicted using docking studies.

ChemInform Abstract: Synthesis of Indazole Motifs and Their Medicinal Importance: An Overview

AbstractReview: 139 refs.

Synthesis of indazole motifs and their medicinal importance: an overview.

Indazoles is an important class of heterocyclic compounds having a wide range of biological and pharmaceutical applications. There is enormous potential in the synthesis of novel heterocyclic systems to be used as building blocks for the next generation of pharmaceuticals as anti-bacterial, anti-depressant and anti-inflammatory. Fused aromatic 1H and 2H-indazoles are well recognized for anti-hypertensive and anti-cancer properties. The present review focuses on novel routes of their synthesis and various biological activities.

Synthesis of novel heterocyclic systems, benzo[b]furobenzimidazoles

Two new tetracyclic heterocompounds are obtained by cyclization under modified Phillips conditions within short reaction times.

ChemInform Abstract: Synthesis of Novel Heterocyclic System 9‐Methyl‐8‐phenyl‐1,4‐dihydro‐5H‐pyrazolo[5′,1′:2,3]pyrimido[4,5‐e] [1,2,4]triazepin‐5‐one.

AbstractThe title compound (IV) is obtained in the reaction of carbohydrazide (II) with triethyl orthoformate.

Synthesis of novel heterocyclic system 9-methyl-8-phenyl-1,4-dihydro-5H-pyrazolo-[5',1':2,3]pyrimido[4,5-e][1,2,4]triazepin-5-one

The title compound (IV) is obtained in the reaction of carbohydrazide (II) with triethyl orthoformate.

Synthesis of novel heterocyclic systems. 2,3-dihydropyrido[1,2-b][1,4,2]oxaselenazin-5-ium

Synthesis of novel heterocyclic systems. 2,3-dihydropyrido[1,2-b][1,4,2]oxaselenazin-5-ium

A novel transformation of 1,2-dithiole-3-thiones into 1,3-thiazine-4-thiones

1,2 Dithiole 3 thiones 1 exhibit a variety of reactivi ties.1 1,3 Dipolar cycloaddition of these compounds is best studied: the reaction involves ring opening with participation of the thione group. Transformations with retention of the thione group are much more uncommon. 1,2 Dithiole 3 thiones have been reported to react with α,β unsaturated nitriles to give thiopyran thiones2 and with amines to give 1,2 thiazole 3 thiones or 1,2 isothiazole 5 thiones.3 We discovered a novel transformation of the dithiole ring. In reactions of 1,2 dithiole 3 thiones 1a—d with 3,4 dihydropyrrolo[1,2 a]pyrazine (2), the imine frag ment of compound 2 is inserted into the 1,2 dithiole ring with extrusion of the S atom (the latter was isolated as elemental sulfur in a nearly quantitative yield) to give fused 1,3 thiazine 4 thiones 3a—d in high yields (Scheme 1). The transformation is possible for both fused (1a—c) and monocyclic 1,2 dithioles (1d). Such reactions in volving the insertion of nitrogen containing fragments into the 1,2 dithiole ring give wide scope for the synthesis of novel heterocyclic systems. The structures of 1,4 thiazine 4 thiones 3a—d were fully confirmed by elemental analysis data and 1H and 13C NMR, IR, and mass spectra. Some of the spectral Scheme 1

Synthesis of Novel Heterocyclic System [1,2,4] Triazolo [4,3,a] pyrimido [4,5-e] [1,3,4] thiadiazines

Article Synthesis of Novel Heterocyclic System [1,2,4] Triazolo [4,3,a] pyrimido [4,5-e] [1,3,4] thiadiazines was published on October 1, 2004 in the journal Heterocyclic Communications (volume 10, issue 4-5).

Condensed Isoquinolines. Part 12. Synthesis of Novel Heterocyclic Systems Containing a Partially Hydrogenated Spiro[isoquinoline‐4,4′‐(2H)‐pyran] Fragment

AbstractFor Abstract see ChemInform Abstract in Full Text.

Condensed Isoquinolines. 12. Synthesis of Novel Heterocyclic Systems Containing a Partially Hydrogenated Spiro[isoquinoline-4,4'-(2H)-pyran] Fragment

By condensation of 4-(2-bromomethyl)-3,4,5,6-tetrahydro-2H-pyran-4-carbonitrile with anthranilic acid, its derivatives substituted in the benzene ring (esters, nitrile), and with esters of 2-aminothiophene-3-carboxylic acids and 3-amino-5-bromobenzofuran-2-carboxylic acid there have been synthesized novel derivatives which include spiro-linked tetrahydropyran and 5,10-dihydro-3H-pyrimido[1,2-b]isoquinoline fragments. The pyrimidine ring of the latter was annelated by a substituted benzene, thiophene, or 5-bromobenzofuran ring.

ChemInform Abstract: 1,5‐Di(tetrazol‐5‐yl)‐3‐oxapentane as a Substrate in the Synthesis of Novel Heterocyclic Systems.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

1,5-Di(tetrazol-5-yl)-3-oxapentane as a substrate in the synthesis of novel heterocyclic systems

The preparation of novel bifunctional and macroheterocyclic systems by N-alkylation and N-acylation of 1,5-di(tetrazol-5-yl)-3-oxapentane has been developed

Base catalyzed rearrangement of bispropargyl sulfides, ethers, and amines. Synthesis of novel heterocyclic systems

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBase catalyzed rearrangement of bispropargyl sulfides, ethers, and amines. Synthesis of novel heterocyclic systemsPeter J. Garratt and Soon Bin NeohCite this: J. Am. Chem. Soc. 1975, 97, 11, 3255–3257Publication Date (Print):May 1, 1975Publication History Published online1 May 2002Published inissue 1 May 1975https://doi.org/10.1021/ja00844a075RIGHTS & PERMISSIONSArticle Views310Altmetric-Citations63LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (356 KB) Get e-Alerts Get e-Alerts