A Simple Synthesis of Dibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridines

Sampathkumar, Natarajan; Kumar, Nikhil; Rajendran, S. P.

doi:10.1081/scc-120037914

Cited by 19 publications

(6 citation statements)

References 6 publications

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“…Due to their biological and synthetic importance, the development of effective routes to synthesize naphthyridines continues to be an active area of research for synthetic organic chemists [11]. A survey of the literature shows that the major synthetic approaches used to prepare the naphthyridine system involved condensation of 2-aminopyridine derivatives with carbonyl compounds containing an activated methylene group [12,13,14,15,16,17,18,19] or with β -ketoesters [20].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

et al. 2015

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Abstract:The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo [3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable OPEN ACCESSMolecules 2015, 20 8500 antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.

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Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

et al. 2015

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“…Few methods are reported for the synthesis of dibenzo[ b , g ][1,8]naphthyridines . Recently, our laboratory focused on the synthesis of dibenzo[ b , g ][1,8]naphthyridines through a novel one‐step reaction of 2‐chloro‐3‐formyl quinolines with aryl amines as well as 1,2,3,4‐tetrahydro‐dibenzo [ b , g ][1,8]naphthyridines from 2‐amino‐3‐formyl quinolines through a Friedlander type condensation reaction.…”

Section: Introductionmentioning

confidence: 99%

A Facile Synthesis of 5‐Phenyl‐Dibenzo[b, g][1,8]Napthyridines

Sampathkumar

Murugesh

Rajendran

2015

Journal of Heterocyclic Chem

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“…Particularly, some dibenzonaphthyridines, that is, quinoline dimers, act as selective 3‐phosphoinositide‐dependent kinase‐I inhibitors . Many reports represent the synthesis of functionalized naphthyridine derivatives , linear dibenzonaphthridines , and angular dibenzonaphthridines , and only very few accomplish their construction through anilinoquinolines .…”

Section: Introductionmentioning

confidence: 99%

Effect of Substituents in the Syntheses of Phenyl‐Substituted Dibenzonaphthyridines

Manickam

Prasad

2013

Journal of Heterocyclic Chem

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A facile and elegant syntheses of linear and angular phenyl‐substituted dibenzonaphthyridines from 2,4‐dichloroquinolines through anilinoquinolines have been developed. The substituents in the 4th position of the anilinoquinoline and the temperature were found to play a vital role in the regulation of the yield towards the synthesis of the final compounds. The methyl group in the 7th position of the naphthyridin‐11‐ones was found to hinder the N‐methylation reaction sterically, consequently increasing the reaction time than other derivatives.

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A Simple Synthesis of Dibenzo[b,g][1,8]naphthyridines

Cited by 19 publications

References 6 publications

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

A Facile Synthesis of 5‐Phenyl‐Dibenzo[b, g][1,8]Napthyridines

Effect of Substituents in the Syntheses of Phenyl‐Substituted Dibenzonaphthyridines

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