Novel antagonists of 5-HT3 receptors. Synthesis and biological evaluation of piperazinylquinoxaline derivatives

Since 1940s, Quinoxaline 1,4-dioxides (QdNO's) are known as potent antibacterial agents, and subtherapeutic levels have been used to promote growth and improve efficiency of feed conversion in animal feed. They have also shown a selective cytotoxicity against hypoxic cells present in solid tumours. Furthermore, recent studies have put in evidence that QdNO's are endowed with antitubercular, antiprotozoal and anticandida activities. On the other hand, several authors have reported about photoallergic and mutagenic effects of some derivatives. QdNO's may also cause the development of antibiotic-resistant bacteria and influence the horizontal transfer of virulence genes between bacteria. In this review article we report the biological properties, the mode of action and Structure Activity Relationship (SAR) studies of the QdNO derivatives. Furthermore, some cytogenetic and genotoxic effects, classical and more recent method of synthesis, the quinoxaline 1,4-dioxides, and some of their most important reactions, were also reported.

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“…BFO's react with this substrate to give 3-amino-2-quinoxalinecarbonitrile 1,4-dioxides (9) [103,105,134,[151][152] showed in Fig. (18).…”

Section: Anti-protozoal and Anti-candida Activitiesmentioning

confidence: 99%

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Carta

Corona²,

Loriga

2005

CMC

136

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“…Quinoxalines and their derivatives are an important class of benzoheterocycles exhibiting a broad spectrum of biological activities [129][130][131][132][133][134][135][136][137] and also found applications as dyes 138,139 and as building blocks in the synthesis of organic semiconductors. 140,141 In 2012, Shaabani et al 142 developed a novel and efficient one-pot multicomponent reaction for the synthesis of 1,6dihydro-6,6-dimethylpyrazine-2,3-dicarbonitriles (38) from the reaction between alkyl or aryl isocyanides (35), 2,3-diaminomaleonitrile (36) and 3-oxopentanedioic acid (37) at room temperature (Scheme 13).…”

Section: Catalyst-free One-pot Multicomponent Reactionsmentioning

confidence: 99%

Design for carbon–carbon bond forming reactions under ambient conditions

Brahmachari

2016

RSC Adv.

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Carbon-carbon (C-C) bond forms the 'backbone' of nearly every organic molecule, and lies at the heart of the chemical sciences! This transformation has always been one of the most useful and fundamental reactions in the development of organic chemistry. Currently, the concept of 'green chemistry' is globally acclaimed and has already advanced quite significantly to come out as a distinct branch of chemical sciences. Among the principles of 'green chemistry', one principle is dedicated to "design of energy efficiency" -that is to develop synthetic strategies that require less/minimum amount of energy to carry out a specific reaction with optimum productivity. And the most effective way-out to save energy is to develop strategies/protocols that are capable enough to carry out the transformations at ambient temperature and pressure! As part of on-going developments on green synthetic strategies, designing for reactions under ambient conditions coupled with other green aspects is, thus, an area of current choice. This review is aimed to offer an up-to-date development on the design of carbon-carbon bond forming protocols to access a wide variety of organic molecules of topical significance under ambient conditions. The account highlights on the brilliant applications of reaction conditions such as the use of solvents or no solvent, catalysts or no catalyst, and the use of green tools like ball-milling, ultrasonication and visible light in achieving the goal! Design for Carbon Carbon Frameworks at Ambient ConditionsN Me Me Me O O COOH Br Br (Graphic for TOC)

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“…Among the various classes of nitrogen containing heterocyclic compounds, quinoxaline derivatives display a broad spectrum of biological activities (Seitz et al, 2002;Monge et al, 1993;Kim et al, 2004). Quinoxalines play an important role as a basic skeleton for the design of a number of antibiotics such as echinomycin, actinomycin and leromycin.…”

Section: Data Collectionmentioning

confidence: 99%

3-[2-(3-Phenyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]-1,3-oxazolidin-2-one

Daouda¹,

Doumbia²,

Essassi³

et al. 2013

Acta Cryst E

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The dihydroquinoxaline ring system of the title molecule, C19H17N3O3, is approximately planar [maximum deviation = 0.050 (2) Å], the dihedral angle between the planes through the two fused rings being 4.75 (8)°. The mean plane through the fused-ring system forms a dihedral angle of 30.72 (5)° with the attached phenyl ring. The molecular conformation is enforced by C—H⋯O hydrogen bonds. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

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Novel antagonists of 5-HT3 receptors. Synthesis and biological evaluation of piperazinylquinoxaline derivatives

Cited by 59 publications

References 11 publications

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Design for carbon–carbon bond forming reactions under ambient conditions

3-[2-(3-Phenyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]-1,3-oxazolidin-2-one

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