Effect of substituents in the dihydropyridine ring on the reactivity of the ester group of 3,5-dialkoxycarbonyl-1,4-dihydropyridines

Chekavichus, B. S.; Sausin, A. E.; Dubur, G. Ya.

doi:10.1007/bf00506586

Cited by 5 publications

(3 citation statements)

References 10 publications

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“…Finally, these last compounds reacted with triethylamine, benzotriazole-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (Bop reagent), and 33% aqueous ammonia under N 2 atmosphere to give the 3,5-diamides 3a − d (Scheme ). Among the synthesized derivatives, compounds 1b , 1c , and their corresponding acids 2b and 2c are known in the literature ( 1b and 2b , 1c , 2c ). Chemical and physical data for compounds 1 − 3 are reported in Table .…”

Section: Chemistrymentioning

confidence: 99%

Study of 1,4-Dihydropyridine Structural Scaffold: Discovery of Novel Sirtuin Activators and Inhibitors

et al. 2009

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NAD(+)-dependent sirtuin deacetylases have emerged as potential therapeutic targets for treatment of human illnesses such as cancer, metabolic, cardiovascular, and neurodegenerative diseases. The benefits of sirtuin modulation by small molecules have been demonstrated for these diseases. In contrast to the discovery of inhibitors of SIRT1, -2, and -3, only activators for SIRT1 are known. Here, we rationalized the potential of the previously unexplored dihydropyridine scaffold in developing sirtuin ligands, thus we prepared a series of 1,4-dihydropyridine-based derivatives 1-3. Assessment of their SIRT1-3 deacetylase activities revealed the importance of the substituent at the N1 position of the dihydropyridine structure on sirtuin activity. Placement of cyclopropyl, phenyl, or phenylethyl groups at N1 conferred nonselective SIRT1 and SIRT2 inhibition activity, while a benzyl group at N1 conferred potent SIRT1, -2, and -3 activation. Senescence assays performed on hMSC and mitochondrial function studies conducted with murine C2C12 myoblasts confirmed the compounds' novel and unique SIRT-activating properties.

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Section: Chemistrymentioning

confidence: 99%

Study of 1,4-Dihydropyridine Structural Scaffold: Discovery of Novel Sirtuin Activators and Inhibitors

et al. 2009

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“…The ester group (COOEt) does not react under these mild conditions, showing that it is deactivated, most probably due to conjugation of the carbonyl function of the COOEt with the NH group in the HN-C=C-C=O(OR) system [14], and the -NH … O=C-hydrogen bonding.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Some Reactions of 3-Chloro-2-(cyanomethylene)-1,2-dihydroquinoxalines

Obafemi

Pfleiderer

2004

Molecules

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2,3-Dichloroquinoxaline and some of its derivatives have been reacted with malononitrile and ethyl cyanoacetate to yield a variety of 3-chloro-2-(cyanomethylene)-1,2-dihydroquinoxaline derivatives. The reaction of 3-chloro-2-(dicyanomethylene)-1,2-dihydroquinoxaline (2e) with pyridine and its methyl derivatives led to the zwitterionic structures 6a-6c. The structures of the newly synthesized compounds were assigned by spectroscopic data and elemental analyses.

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“…Substituents at positions 3 and 5 of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates have crucial influence on biological activities and chemical properties such as hydrolysis, and transesterification [4]. Thus, alkyl esters at positions 3 and 5 of 1,4-DHP are exceptionally stable upon treatment with nucleophilic reagents due to electronic and steric reasons [5]. In the case of ethoxycarbonylmethyl 1,4-dihydropyridine-3-carboxylates, alkaline and enzyme-catalysed hydrolysis takes place only at the more remote from the 1,4-DHP cycle ester groups forming the corresponding carboxymethyl esters because of steric and electronic factors [6,7].…”

Section: Introductionmentioning

confidence: 99%

Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates

et al. 2015

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Abstract:The ethoxycarbonylmethyl esters of 1,4-dihydropyridines were directly converted into carbamoylmethyl esters in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in good to excellent yields under mild conditions. The use of TBD is crucial for the successful aminolysis of ethoxycarbonylmethyl ester of 1,4-dihydropyridines with secondary amines as without it the reaction does not proceed at all. The aminolysis reaction proceeded regioselectively, as the alkyl ester conjugated with the 1,4-dihydropyridine cycle was not involved in the reaction.

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Effect of substituents in the dihydropyridine ring on the reactivity of the ester group of 3,5-dialkoxycarbonyl-1,4-dihydropyridines

Cited by 5 publications

References 10 publications

Study of 1,4-Dihydropyridine Structural Scaffold: Discovery of Novel Sirtuin Activators and Inhibitors

Study of 1,4-Dihydropyridine Structural Scaffold: Discovery of Novel Sirtuin Activators and Inhibitors

Synthesis and Some Reactions of 3-Chloro-2-(cyanomethylene)-1,2-dihydroquinoxalines

Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates

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