Reactions of Bisazomethines of the Naphtalene Series with 1,3-Diketones

Козлов, С. Н.; Basalaeva, L. I.; Ol’khovik, V. K.; Kalechits, G. V.; Matveenko, Yu. V.

doi:10.1023/b:rugc.0000015994.57381.23

Cited by 5 publications

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“…First, (1,1′-biphenyl)-4,4′-diyldimethanol was reacted with pyridinium chlorochromate (PCC) at room temperature to form the (1,1′-biphenyl)-4,4′-dicarbaldehyde intermediate; then it was condensed with appropriate amines to achieve the final compounds. [29][30][31] Unlike biphenyl-diimine derivatives, the synthesis of the biphenyl-diazo compounds was realized in one step as illustrated in Scheme 2. 4,4′-Dinitrobiphenyl was reacted with appropriate anilines at 150°C with potassium hydroxide (KOH).…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, acetylcholinesterase, butyrylcholinesterase, and amyloid‐β aggregation inhibition studies of substituted 4,4ʹ‐diimine/4,4ʹ‐diazobiphenyl derivatives

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Tarikogullari

Alptüzün

et al. 2022

Archiv der Pharmazie

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A series of 4,4′-diimine/4,4′-diazobiphenyl derivatives were designed, synthesized, and evaluated for their ability to inhibit both the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes, as well as Aβ 1-42 aggregation, in vitro. The AChE and BChE inhibition assays demonstrated that all compounds displayed moderate AChE inhibitory activity in the range of IC 50 = 5.77-16.22 μM, while they displayed weak or no BChE inhibition. Among the title compounds, compound 2l, 4,4′-bis(quinolin-8yldiazenyl)-1,1′-biphenyl, having a diazo-quinoline moiety demonstrated the most potent inhibition against AChE with an IC 50 value of 5.77 μM. Furthermore, diazo derivatives 2d, 4,4′-bis[(4-methoxyphenyl)diazenyl]-1,1′-biphenyl, and 2i, 4,4′-bis(pyridin-3-yldiazenyl)-1,1′-biphenyl, provided better potency on Aβ 1-42 aggregation, with an inhibition value of 74.08% and 78.39% at 100 μM and 55.35% and 61.36% at 25 μM, respectively. Molecular modeling studies were carried out for the most active compound against AChE, compound 2l. All the results suggested that compounds 2d and 2i have better inhibitory potencies on Aβ 1-42 aggregation and moderate AChE enzyme activity, and therefore can be highlighted as promising compounds.

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Section: Chemistrymentioning

confidence: 99%

Design, synthesis, acetylcholinesterase, butyrylcholinesterase, and amyloid‐β aggregation inhibition studies of substituted 4,4ʹ‐diimine/4,4ʹ‐diazobiphenyl derivatives

Parlar

Tarikogullari

Alptüzün

et al. 2022

Archiv der Pharmazie

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“…Thanks to its high reactivity, indan-1,3-dione is widely used in synthetic organic chemistry, including the synthesis of heterocyclic compounds [1,3].…”

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Vanillin esters in reactions with indan-1,3-dione

Козлов¹,

Basalaeva²

2006

Chem Heterocycl Compd

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Keywords: 2-arylidenindan-1,3-diones, O-acylvanillins, indan-1,3-dione, 2-methoxy-4-(12-oxo-12H-benzo[f]indeno[1,2-b]quinolin-13-yl)phenyl esters of carboxylic acids, 2-naphthylamine.Thanks to its high reactivity, indan-1,3-dione is widely used in synthetic organic chemistry, including the synthesis of heterocyclic compounds [1,3].In the present work we have presented the results of a study of a three component condensation of indan-1,3-dione 1, 2-naphthylamine 2, and vanillin esters 3a-h. The condensation was carried out by heating equimolar amounts of the components in ethanol. We assumed that formation of the final heterocyclic compound of the indenoquinoline series occurred via intermediate amino ketone A, which then lost a water molecule and cyclized to the corresponding 4-(12,13-dihydro-12-7H-benzo[f]indeno[1,2-b]quinolin-13-yl)-2-methoxyphenyl esters of the carboxylic acids 5a-h. Oxidation of the latter gave 2-methoxy-4-In all the experiments under the experimental conditions the esters 5a-h were found in mixtures with 2-methoxy-4-(12-oxo-12H-benzo[f]indeno[1,2-b]quinolin-13-yl)phenyl esters of the carboxylic acids 6a-h in a ratio of 1:9 according to the 1 H NMR spectra. At recrystalization of compounds 5a-h their further oxidation occurs and separation of them from the reaction mixture in pure form proved impossible. In view of the difficulty of separating compounds 5a-h and 6a-h, immediate dehydration of the mixture obtained by boiling in nitrobenzene for 3-4 h was carried out.During monitoring of the course of the reaction we established that 4-[(1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)methyl]-2-methoxyphenyl esters of the carboxylic acids 4a-h were always present in the reaction mixture. From this it can be proposed that condensed reaction products of the dihydrobenzoindenoquinoline series 5a-h are formed by reaction of the 2-arylideneindan-1,3-diones 4a-h with 2-naphthylamine 2.To confirm this idea we have synthesized 4-[(1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)methyl]-2-methoxyphenyl esters of the carboxylic acids 4a-h by the reaction of indan-1,3-dione with O-acylvanillins 3a-h and condensing them with 2-naphthylamine 2 under analogous conditions. Mixtures of the esters 5a-h and 6a-h were formed as a result of the condensation, analogous to the mixtures from the three component condensation of compounds 1, 2, and 3a-h.

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