Synthesis and structure of 3-oxopyrano[3,4-c]pyridines

Paronikyan, E. G.; Sirakanyan, S. N.; Lindeman, Sergey V.; Aleksanyan, M. S.; Karapetyan, A. A.; Noravyan, A. S.; Struchkov, Yu. T.

doi:10.1007/bf00479620

Cited by 10 publications

(9 citation statements)

References 3 publications

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“…The structure of newly obtained compounds 2a – d , g , h (the physico-chemical characterization of compounds 2e , f [ 7 , 8 ] and 2i – o [ 9 ] were already reported) was confirmed by NMR, IR spectroscopy and by elemental analysis. Thus, in the 1 H-NMR spectra of these new compounds 2a – d , g , h the presence of the NH group proton at 12.05−12.19 ppm was observed.…”

Section: Resultsmentioning

confidence: 65%

“…For the first time a “one-pot” synthetic method for the preparation of new as well as already known 3-oxo derivatives of cyclopenta[ c ]pyridine 2a – d , of 5,6,7,8-tetrahydroisoquinoline [ 7 , 8 ] 2e – h and of pyrano[3,4- c ]pyridine [ 9 ] 2i – o was developed and is described. Thus, the reaction of ketones 1 with morpholine in anhydrous benzene led to the formation of the corresponding enamines.…”

Section: Resultsmentioning

confidence: 99%

“…After, the acylation of the enamines, followed by the cyclocondensation intermediate compounds with 2-cyanoacetamide in the presence of diethylamine led to the formation of the aimed compounds 2a – o in good to high yields ( Scheme 1 ). This approach of synthesis for compounds 2 was not described in the literature but, although no significant difference was observed in terms of yields compared to the already described multistep synthesis of these compounds 2 [ 7 , 8 , 9 ], it has some advantages: it reduces the time required to obtain these compounds, requires fewer reagents and solvents, and is less laborious.…”

Section: Resultsmentioning

confidence: 99%

“…+44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ). Compounds 2e , f [ 7 , 8 ] , 2i – o [ 9 ] , 3a , b , d – m , o [ 6 , 10 , 11 , 12 , 13 ] , and 4a , b , d , e , g – m , o [ 6 , 10 , 11 , 12 , 13 ] were already described.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Neurotropic Activity of New Heterocyclic Systems: Pyridofuro[3,2-d]pyrrolo[1,2-a]pyrimidines, Pyridofuro[3,2-d]pyrido[1,2-a]pyrimidines and Pyridofuro[3′,2′:4,5]pyrimido[1,2-a]azepines

et al. 2021

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Background: Neurotic disturbances, anxiety, neurosis-like disorders, and stress situations are widespread. Benzodiazepine tranquillizers have been found to be among the most effective antianxiety drugs. The pharmacological action of benzodiazepines is due to their interaction with the supra-molecular membrane GABA-a-benzodiazepine receptor complex, linked to the Cl-ionophore. Benzodiazepines enhance GABA-ergic transmission and this has led to a study of the role of GABA in anxiety. The search for anxiolytics and anticonvulsive agents has involved glutamate-ergic, 5HT-ergic substances and neuropeptides. However, each of these well-known anxiolytics, anticonvulsants and cognition enhancers (nootropics) has repeatedly been reported to have many adverse side effects, therefore there is an urgent need to search for new drugs able to restore damaged cognitive functions without causing significant adverse reactions. Objective: Considering the relevance of epilepsy diffusion in the world, we have addressed our attention to the discovery of new drugs in this field Thus our aim is the synthesis and study of new compounds with antiepileptic (anticonvulsant) and not only, activity. Methods: For the synthesis of compounds classical organic methods were used and developed. For the evaluation of biological activity some anticonvulsant and psychotropic methods were used. Results: As a result of multistep reactions 26 new, five-membered heterocyclic systems were obtained. PASS prediction of anticonvulsant activity was performed for the whole set of the designed molecules and probability to be active Pa values were ranging from 0.275 to 0.43. The studied compounds exhibit protection against pentylenetetrazole (PTZ) seizures, anti-thiosemicarbazides effect as well as some psychotropic effect. The biological assays evidenced that some of the studied compounds showed a high anticonvulsant activity by antagonism with pentylenetetrazole. The toxicity of compounds is low and they do not induce muscle relaxation in the studied doses. According to the study of psychotropic activity it was found that the selected compounds have an activating behavior and anxiolytic effects on the models of “open field” and “elevated plus maze” (EPM). The data obtained indicate the anxiolytic (anti-anxiety) activity of the derivatives of pyrimidines, especially pronounced in compounds 6n, 6b, and 7c. The studied compounds increase the latent time of first immobilization on the model of “forced swimming” (FST) and exhibit some antidepressant effect similarly to diazepam. Docking studies revealed that compound 6k bound tightly in the active site of GABAA receptor with a value of the scoring function that estimates free energy of binding (ΔG) at −7.95 kcal/mol, while compound 6n showed the best docking score and seems to be dual inhibitor of SERT transporter as well as 5-HT1A receptor. Conclusions: Тhe selected compounds have an anticonvulsant, activating behavior and anxiolytic effects, at the same time exhibit some antidepressant effect.

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Section: Resultsmentioning

confidence: 65%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis and Neurotropic Activity of New Heterocyclic Systems: Pyridofuro[3,2-d]pyrrolo[1,2-a]pyrimidines, Pyridofuro[3,2-d]pyrido[1,2-a]pyrimidines and Pyridofuro[3′,2′:4,5]pyrimido[1,2-a]azepines

et al. 2021

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“…IR spectra, ν, cm -1 : 3320 (NH), 1600 (C=C Ar). 1 H NMR spectrum, δ, ppm (J , Hz): 1.28 (6H, d, 3 J = 6.7, CH(CH 3 ) 2 ); 1.36 (6H, s, C(CH 3 ) 2 ); 2.26 (6H, s, N(CH 3 ) 2 ); 2.56 (2H, t, 3 J = 6.5, CH 2 N(CH 3 ) 2 ); 3.04 (1H, sept, 3 J = 6.7, CH(CH 3 ) 2 ); 3.32 (2H, s, CH 2 ); 3.64 (2H, td, 3 J = 6.5, 3 J = 5.8, NHCH 2 ); 4.86 (2H, s, OCH 2 ); 7.40 (1H, t, 3 . IR spectrum, ν, cm -1 : 3350 (NH), 1610 (C=C Ar).…”

Section: Synthesis Of Compounds 6a-t (General Method)mentioning

confidence: 98%

Synthesis of 8-amino derivatives of condensed furo[3,2-d]pyrimidines

Sirakanyan

Paronikyan

Ghukasyan

et al. 2010

Chem Heterocycl Comp

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We have previously reported on the synthesis of condensed thieno [3,2-d]pyrimidines [1,2]. The present work is concerned with the extension of our studies in this field to the synthesis of condensed derivatives of furo[3,2-d]pyrimidines. As starting compounds we used 6-oxo derivatives of pyrano[3,4-c]pyridines 1 [3] which on interaction with ethyl chloroacetate were converted into the corresponding O-alkylated derivatives 2. Cyclization of the latter into furo[2,3-b]pyridines 3 occurred only in absolute ethanol under the influence of sodium ethoxide. The presence in the furan ring of compound 3 of two similar functional groups permits cyclization by condensation of the latter with formamide. As a result we synthesized the condensed furo-[3,2-d]pyrimidones 4 which were converted into the corresponding chloro derivatives 5 under the influence of phosphorus oxychloride. Further reaction of the chloride with various amines led to the required 8-amino derivatives 6. EXPERIMENTALIR spectra of nujol mulls were recorded with a UR-20 spectrometer. 1 H NMR spectra of DMSO-d 6 solutions with TMS as internal standard were recorded on a Varian Mercury-300VX (300 MHz) instrument.The course of reactions and the purity of the compounds synthesized were monitored by TLC on Silufol UV-254 plates. Synthesis of Compounds 2a,b (General Method).Ethyl chloroacetate (13.48 g, 0.11 mol) was added dropwise with stirring to a suspension of pyrano[3,4-c]pyridine 1a,b (0.1 mol) and potash (15 g, 0.11 mol) in dry DMF (150 ml). The temperature of the reaction mixture was maintained at 75-80°C for 2 h, then cooled to room temperature, and poured into cold water. The crystals of compound 2 formed were filtered off, washed with water, dried, and recrystallized from ethanol.

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