Iodine catalysed first synthesis of 2-Quinolone-Benzothiazolo-Quinazolinone derivatives
TL;DR: In this article, multi-component reactions to form heterocyclic compounds possessing quinolone, benzothiazole or quinazolinone moieties are very well-known.
Abstract: Multi-component reactions to form heterocyclic compounds possessing quinolone, benzothiazole or quinazolinone moieties are very well-known. Various derivatives of these molecules exhibit remarkable...
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TL;DR: In this article , the authors review all important multicomponent reactions catalyzed by molecular iodine reported since 2013 in order to envisage some new efficient protocols for the synthesis of structurally complex molecules.
Abstract: In multicomponent reactions, three or more reactants combine in one pot to form a product without the isolation of intermediate and most of the reactants contribute to newly formed product reducing number of steps involved and waste generated. Molecular iodine is mild, efficient, relatively nontoxic, inexpensive, commercially available, and catalyzes various organic reactions due to its Lewis acidic behaviour. The development of multicomponent reactions catalyzed by molecular iodine indeed is a good green alternative for synthetic organic chemistry. The aim of this article is to review all important multicomponent reactions catalyzed by molecular iodine reported since 2013 in order to envisage some new efficient protocols for the synthesis of structurally complex molecules.
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TL;DR: In this paper , the authors outline the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.
Abstract: Quinoline is a significant scaffold among heterocyclic compounds and can be used as a key building block for the development of novel medications. Quinoline and its derivatives are recognised as biologically active substances with a number of pharmacological properties. Nowadays, quinoline- based heterocycle scaffolds have achieved a prominent position in medicinal chemistry due to their significant pharmacological and biological properties. The discovery and creation of cutting-edge medications to treat a variety of diseases is an example of the usefulness of these compounds. The current study outlines the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.
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TL;DR: In this article , a new strategy is developed to synthesize different quinoline-based quinazolinones catalytically using InCl3 through a cyclocondensation reaction of isatoic anhydride and aniline with 2-substituted-quinoline-3-carbaldehyde to produce 2-(2-phenoxyquinolin-3yl)-3-phenyl-2,3- dihydroquinazolin-4(1H)-one derivatives (>90 % yields).
Abstract: Quinoline-based compounds are one of the most important classes of N-heterocyclics exhibiting a wide spectrum of biological activities. There is a constant demand for the synthesis of new quinoline-based molecules suitable for therapeutic applications. Here a new strategy is developed to synthesize different quinoline-based quinazolinones catalytically using InCl3 through a cyclocondensation reaction of isatoic anhydride and aniline with 2-substituted-quinoline-3-carbaldehyde to produce 2-(2-phenoxyquinolin-3-yl)-3-phenyl-2,3- dihydroquinazolin-4(1H)-one derivatives (>90 % yields). In contrast, the reduced electrophilicity at the metal center allows the hydrazide ligand to bind In(III) and serendipitously forms benzoic(2-phenoxyquinoline-3-carbonyl) carbamic anhydride (∼70 % yields). The mechanistic aspects of these reactions were rationally explained. The structure and purity of all the isolated derivatives were assessed by spectroscopic and analytical data. In view of a strong correlation existing between inflammation and cancer progression, the ex-vivo anti-inflammatory effect of the ligands was established. The anti-cancer property of the proposed ligand was delineated with a specific SIRT protein family. Further, the computational docking studies on the binding abilities of 22 synthesized compounds with the Sirt1 protein were discussed in detail.
TL;DR: In this article , a novel and efficient iodine-promoted bimolecular annulation of 2-benzylidene 1,3-indandiones has been developed, which features mild conditions, short reaction time, high efficiency, good chemoselectivity and remarkable functional group tolerance.
Abstract: Abstract A novel and efficient iodine-promoted bimolecular annulation of 2-benzylidene 1,3-indandiones has been developed. Following this protocol, a series of spirocyclopropane derivatives were furnished in good to excellent yields. The present protocol features mild conditions, short reaction time, high efficiency, good chemoselectivity and remarkable functional group tolerance. Graphical Abstract
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11 Sep 2006TL;DR: It is shown that domino reactions initiated by oxidation or reduction or reduction, as well as other mechanisms, can be inhibited by various materials, such as Na6(CO3)(SO4), Na2SO4, Na2CO3, and so on.
Abstract: Introduction Cationic domino reactions Anionic domino reactions Radical domino reactions Pericyclic domino reactions Photochemically induced domino processes Transition metal catalysis Domino reactions initiated by oxidation or reduction Enzymes in domino reactions Multicomponent reactions Special techniques in domino reactions
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TL;DR: Six of the 6-substituted heterocyclic 2-phenyl-4-quinozolinones showed significant cytotoxicity against a panel of human tumor cell lines with EC(50) values in the low micromolar to nanomolar concentration ranges.
Abstract: As part of our continuing search for potential anticancer candidates among 2-phenyl-4-quinolones and 2-phenyl-4-quinazolinones, two series of 6,7,2‘,3‘,4‘,5‘-substituted 2-phenyl-4-quinazolinones a...
383 citations
TL;DR: Two multicomponent reactions, the Ugi and Passerini reactions, are accelerated by the use of aqueous solutions, allowing direct isolation by precipitation in the preparation of small combinatorial libraries.
Abstract: Two multicomponent reactions, the Ugi and Passerini reactions, are accelerated by the use of aqueous solutions. The rate enhancements compared to those by organic solvents can approach 300-fold. Reactions performed in water offer another advantage that products are often insoluble, permitting direct isolation by precipitation. The methods were applied to the preparation of three small combinatorial libraries.
369 citations
TL;DR: Five series of thiourea derivatives bearing benzothiazole moiety were efficiently synthesized and evaluated for antimicrobial and anticancer activities and showed higher activity against fungi than bacteria.
Abstract: Five series of thiourea derivatives bearing benzothiazole moiety (20 compounds) were efficiently synthesized and evaluated for antimicrobial and anticancer activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bacteria. Compounds 1b, 2b, 3b, 4b and 5b exhibited the greatest antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electronic factors in benzothiazole rings had a great effect on the antimicrobial activity of these compounds. In preliminary MTT cytotoxicity studies, the thiourea derivatives (2d, 5c and 5d) were found most potent. In MCF-7 and HeLa cells, the IC(50) values were observed in the range of 18-26 microM and 38-46 microM, respectively.
354 citations