1,8-Naphthyridine-3-carboxamide derivatives with anticancer and anti-inflammatory activity

Kumar, Vivek; Jaggi, Manu; Singh, Anu; Madaan, Alka; Sanna, Vinod K.; Singh, Pratibha; Sharma, Pramod Kumar; Irchhaiya, Raghuveer; Burman, Anand C.

doi:10.1016/j.ejmech.2009.03.015

Cited by 42 publications

(23 citation statements)

References 12 publications

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“…The deprotection of the BOC group was conducted according to the literature procedure 18. A portion of the impure BOC‐protected compound 9 (130 mg, still contaminated with urea derivative) was dissolved in trifluoroacetic acid (1.5 mL) and dichloromethane (1.5 mL) and stirred at 0 °C for 1 h. After warming to room temperature, the solution was stirred for further 15 h. The solution was neutralized with an aqueous solution of NaHCO 3 and extracted with dichloromethane (3×20 mL).…”

Section: Methodsmentioning

confidence: 99%

Tuning the Redox Properties of Photochromic Diarylethenes by Introducing Electron‐Withdrawing Substituents

Berberich

Würthner

2013

Asian J Org Chem

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A series of seven photochromic diarylethenes (DAEs) with various electron‐withdrawing substituents and their respective closed‐form isomers (DAEC) were synthesized and the optical and redox properties of these photochromes were investigated by UV/vis absorption spectroscopy and cyclic voltammetry. Our comparative studies with these DAEs revealed that the absorption properties of the closed forms and the redox potentials of the open and closed isomers appreciably depend on the number and nature of the electron‐withdrawing groups introduced into the DAE unit. The DAE derivatives can be photochemically switched between two different states with different redox properties. Most prominently, photochrome 3 with two nitro groups has a first reduction potential for the open form 3 o of −1.51 V and for the corresponding closed form 3 c of −0.96 V, and, therefore, is particularly interesting as switchable electron‐acceptor moiety in photochromic systems.

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Section: Methodsmentioning

confidence: 99%

Tuning the Redox Properties of Photochromic Diarylethenes by Introducing Electron‐Withdrawing Substituents

Berberich

Würthner

2013

Asian J Org Chem

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“…Our group has specifically explored 1,8-naphthyridine-3-carboxamide derivatives for in vitro anti-inflammatory activity via modulation of the cytokine arm. For the first instance, we demonstrated the inhibitory action of this class of compounds on cytokines TNF-a, MIP-1-a, IL-1-b, IL-6 secreted by key immune cells such as dendritic cells (DC) against LPS-induced levels in vitro [100,101]. Immunostimulatory potential of compounds of this series was also assessed by enhancement of secretion of cytokines in dendritic cellsbased assay from the basal levels [102].…”

Section: Antiviral Activity (Hiv/hcv)mentioning

confidence: 98%

“…The study identified three compounds of interest, 1-phenyl-3- (100) have also demonstrated anti-allergic activity [163]. Another compound, Sch 37224, 1-(1,2-dihydro-4-hydroxy-2-oxo-1-phenyl-1,8-naphthyridin-3-yl)pyrrolidinium (101) has been reported as leuketriene inhibitor. This compound was able to inhibit leukotriene LTD4 and thromboxane B2 release by anaphylactic guinea pig lung [164].…”

Section: Anti-allergic Activitymentioning

confidence: 98%

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Madaan

Verma

Kumar

et al. 2015

Archiv der Pharmazie

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The 1,8-naphthyridine group of compounds have gained special attention of researchers on account of their demonstrating a variety of interesting biological activities. A wide range of biological properties establishes them as potent scaffolds in therapeutic and medicinal research. The broad spectrum of activities primarily includes antimicrobial, antiviral, anticancer, anti-inflammatory, and analgesic activities. 1,8-Naphthyridine derivatives have also exhibited potential applications in neurological disorders such as Alzheimer's disease, multiple sclerosis, and depression. In addition, these synthetic derivatives have been found to possess activities such as anti-osteoporotic (α(v)β(3) antagonists), anti-allergic, antimalarial, gastric antisecretory, bronchodilator, anticonvulsant, anti-hypertensive, platelet aggregation inhibition, anti-oxidant, EGFR inhibition, protein kinase inhibition, ionotropic agent, β-3 antagonist, MDR modulator, adenosine receptor agonist, adrenoceptor antagonist, and pesticide activities. In spite of the widespread application of the 1,8-naphythyridine scaffolds, only a limited number of review articles are available till date. In this review, we attempt to compile and discuss the key data available in the literature for the multiple biological activities of 1,8-naphthyridine derivatives, in a chronological manner. This review compilation (with 199 references) may be helpful in understanding the diverse biological properties of 1,8-naphthyridines and provide insights into their mechanism of action. This may direct future research in the synthesis of new derivatives and exploring this scaffold for other possible biological activities.

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“…The Vilsmeier cyclization of N-(pyridine-2-yl)acetamide was carried out by adding POCl3 to substrate in DMF at 0-5 °C followed by heating to 90 °C [21] (Scheme 1)…”

Section: Synthesismentioning

confidence: 99%

Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine

Saleh

Ayoub

2014

Eur. J. Chem.

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A simple and regioselective synthesis of 2-chloro-3-formyl-1,8-naphthyridine, through Vilsmeier-Haack cyclization of N-(pyridin-2-yl)acetamide has been reported. The reaction of 2-chloro-3-formyl-1,8-naphthyridine is also investigated and new series of 1,8-naphthyridine derivatives such as 3-chloro-4-(2-chloro-1,8-naphthyridine-3-yl)-1-(phenylamino)azetidin-2one, 3-chloro-4-(2-chloro-1,8-naphthyridin-3yl)-1-((4-nitrophenyl) amino)-azetidin-2-one and 3-chloro-4-(2-chloro-1,8-naphthyridine-3-yl)-1-((2,4-dinitrophenyl) amino)-azetidin-2one have been prepared. The formyl group in the 1,8-naphthyridine is subjected to further transformation into alkoxy carbonyl (NIS-K2CO3/alcohol) to afford 3-alkoxy carbonyl-1,8naphthyridine and new hetero cyclic compounds such as oxadiazolo, thiadiazolo-thion and triazolo-thion have been prepared. The reaction between 2-chloro-3-formyl-1,8naphthyridine and sodium sulphide in DMF produced 2-mercapto-3-formyl-1,8naphthyridine. Some of the prepared compounds were found to have good biological activity against Staphylococcus aureus and Staphylococcus epidermidis.Triazol Thiadizol Azetidine Oxadiazol Naphthyridine Vilsmeier-Haack

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1,8-Naphthyridine-3-carboxamide derivatives with anticancer and anti-inflammatory activity

Cited by 42 publications

References 12 publications

Tuning the Redox Properties of Photochromic Diarylethenes by Introducing Electron‐Withdrawing Substituents

Tuning the Redox Properties of Photochromic Diarylethenes by Introducing Electron‐Withdrawing Substituents

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine

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