67992-11-4Relevant academic research and scientific papers
Design,: In silico studies, and synthesis of new 1,8-naphthyridine-3-carboxylic acid analogues and evaluation of their H1R antagonism effects
Gurjar, Vinod Kumar,Pal, Dilipkumar
, p. 13907 - 13921 (2020)
New 1,8-naphthyridine-3-carboxylic acid derivatives were designed, synthesized and evaluated for their in vivo antihistaminic activity on guinea pig trachea by using chlorpheniramine as the standard drug. It was found that compound 5a1 displayed a promising bronchorelaxant effect in conscious guinea pigs using the in vivo model. A molecular docking study was performed to understand the molecular interaction and binding mode of the compounds in the active site of the H1 receptor. Furthermore, in silico computational studies were also performed to predict the binding modes and pharmacokinetic parameters of these derivatives. Prior to the start of experimental lab work, PASS software was used to predict the biological activities of these compounds. An in silico PASS, Swiss ADME assisted docking approach was found to be suitable to derive and synthesize effective antihistaminic agents for the present study.
A simple and efficient synthesis of novel naphthyridine-1-H-pyrazole-4- carboxylic acid esters/carbaldehydes using Vilsmeier-Haack reagent
Chaitanya, Muggu V.S.R.K.,Dubey, Pramod K.
, p. 49 - 55 (2013/05/23)
The reaction of hydrazide 4 with β-keto esters 5 gave hydrazones 6. Cyclization of 6 with Vilsmeier-Haack reagent (DMF-POCl3 ) for 20 min at room temperature gave 1-(4-oxo-1,4-dihydro-[ 1 ,8]naphthyridine-3-carbonyl)- 1 H -pyrazole-4-carboxylic acid ethyl esters 7. The treatment of 4 with substituted acetophenones 8 yielded the corresponding hydrazones 9 of substituted aceto phenones. The treatment of 9 with Vilsmeier-Haack reagent (DMF-POCl3) for 30 min at room temperature gave product 10, the reaction of which with (diacetoxyiodo)benzene in ethanol at room temperature for 12 h in the presence of molecular iodine furnished 7.
A rapid and convenient synthesis of naphthyridinoyl pyrazolidinones under microwave irradiation condition
Chaitanya, Muggu V.S.R.K.,Dubey, Pramod K.
, p. 368 - 374 (2012/08/28)
Microwave-assisted synthesis of naphthyridinoylpyrazolidinones (7a-7j) has been achieved rapidly via the reaction of naphthyridine hydrazide (4) with different β-keto esters and ethoxymethylenemalonic ester (EMME) (5a-5e). Initially, the reaction of naphthyridine hydrazide (4) with various β-keto esters under microwave irradiation for 5 mins at 130oC results in the formation of condensed products 6a-6j. This condensation was followed by cyclization, also, in diphenyl ether under microwave irradiation for 10 mins at 230-250oC, yielding the corresponding cyclized products 7a-7j. Alternatively, both reactants 4 and each of the β -keto esters/EMME (5a-5e) were treated in diphenyl ether under microwave irradiation for 15 mins at 230-250oC giving the target molecules 7a-7j as one-pot reaction in good yields.
Efficient synthesis of novel 3-[5-(1H-benzimidazol-2-ylmethanesulfonyl)-4- phenyl-4H-(1,2,4)triazol-3-Yl]-1H-(1,8)naphthyridin-4-one derivatives
Venkateshwarlu,Chaitanya,Dubey
scheme or table, p. 711 - 721 (2012/06/29)
of 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbohydrazide (4) with substituted phenyl isothiocyanates (5) in ethanol under reflux for 30 min gave thiosemicarbazide derivatives 6, which on cyclization in 2N NaOH under refluxing conditions for 1 h resulted in 3-(5-mercapto- 4-phenyl-4H-1,2,4-triazol-3-yl)- 1,8-naphthyridin-4(1H)-one (7). Alternatively, 7 could also be prepared from following sequence of reactions, i.e., 4→8→7. In another sequence of reactions, condensation of 7 with chloroacetic acid in dimethylformamide (DMF) and K2CO3 as a mild base at 120 °C for 2 h resulted in 2-((5-(1,4-dihydro-4-oxo-1,8-naphthyridin-3-yl)-4-phenyl-4H-1,2,4-triazol-3-yl) sulfanyl)acetic acid (10). The latter, on reaction with substituted o-phenylenediamine (11) in 6N HCl for 4 h yielded 3-(5-((1H-benzo[d]imidazol-2- yl)methylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-1,8-naphthyridin-4(1H)-one (12). Alternatively, 12 could also be prepared by reacting 7 with 13 in DMF and K 2CO3 as a mild base at 120 °C for 2 h, followed by oxidation with H2O2 resulting in the corresponding sulfonyl derivatives 14. Copyright
Synthesis of novel napththyridines as potential antibacterial agents
Chaitanya,Dubey
, p. 105 - 108 (2013/09/23)
The reaction of 2-aminopyridine (1) with ethoxymethylenemalonic ester gave 4-ethoxy-3-oxo-2-(pyridine-2-yl aminomethylene)-butyric acid ethyl ester (2) which on cyclization in the presence of hot PPA gave 4-oxo-1,4-dihydro-[1,8] naphthyridine-3-carboxylic
A facile and convenient synthesis of naphthyridinoyl pyrazoles
Chaitanya,Dubey
, p. 109 - 112 (2013/09/23)
The reaction of naphthyridine hydrazide (4) with each of the different β-keto esters like ethyl 2-chloroacetoacetate (5), ethyl benzoylacetate (6) and ethyl 4-chloroacetoacetate (7) and with ethoxymethylenemalonic ester (8), independently, in ethanol, resulted in the formation of condensed products 2-chloro-3-[4-oxo-1,4-dihydro-[1,8] naphthyridine-3-carbonyl hydrazono]-butyric acid ethyl ester (9), 3-[(4-oxo-1,4-dihydro-[1,8] naphthyridine-3-carbonyl)- hydrazono]-3-phenyl propionic acid ethyl ester (10), 4-chloro-3-[(4-oxo-1,4- dihydro-[1,8] naphthyridine-3-carbonyl)-hydrazono]-butyric acid ethyl ester (11) and 2-[N-(6-bromo-4-oxo-1,4-diydro-[1,8] naphtyiridine-3-carbonyl- hydrazinomethylene)-malonic acid diethyl ester] (12) respectively. Each of these on heating with diphenyl ether yielded the corresponding cyclized products 3-(4-chloro-3-methyl-5-oxo-4,5-dihydro-pyrazole-1-carbonyl)-1H-[1,8] naphthyridin-4-ohe (13), 3-(5-oxo-3-phenyl-4,5-dihydro-pyrazole-1-carbonyl)-1H- [1,8] naphthyridine-4-one (14), 3-(3-chloromethyl-5-oxo-4,5-dihydropyrazole-1- carbonyl)-1 H-[1,8] naphthyridine-4-one (15) and 3-(4-chloro-3-methyl-5-oxo-4,5- dihydropyrazole-1-carbonyl)-1H-[1,8] naphthyridin-4-one (16). Alternatively, treatment of naphthyridine hydrazide (4) with each of the β-keto esters 5,6 & 7 and with EMME (8) directly in diphenylether at 2507deg; as one-pot reaction, gave the final products 13,14,15 & 16 in good yields.
