Styrylbenzodiazinones 1. Synthèse, structure et propriétés photophysiques

Cazaux, Louis; Faher, Mourad; Picard, Claude; Tisnès, P.

doi:10.1139/v93-250

Cited by 17 publications

(12 citation statements)

References 4 publications

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“…Alkylation of quinoxalinones, in the presence of bases, generally affords mixtures of N 1 -alkylquinoxalino-2-ones and 2-alkoxyquinoxalines [2,[165][166], but in a few cases only the N 1 -alkylquinoxalino-2-ones are obtained [167][168]. Some examples are reported in Fig.…”

Section: Reactions Of Quinoxalin-2-onesmentioning

confidence: 99%

“…Likewise, both ethyl 2-oxo-3-quinoxalinecarboxylates and unsubstituted quinoxalinone react with ethyl iodide and -phenylalkylhalogens, under sodium hydride catalysis, affording the corresponding mixtures (4 and 5) [2] and (6 and 7) [165]. On the other hand, methylation of 3-azidoquinoxalin-2-one and 3-methylquinoxalin-2-one with methyl iodide and methyl paratoluenesolphonate respectively, both in the presence of potassium carbonate, afford the N 1 -alkylquinoxalino-2-ones (8) [167] and (9) only [168].…”

Section: Reactions Of Quinoxalin-2-onesmentioning

confidence: 99%

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Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Carta

Piras²,

Loriga

et al. 2006

MRMC

221

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Quinoxaline derivatives have received much attention in recent years owing to their both biological properties and pharmaceutical applications. In this review we focus the attention on quinoxalin-2(3)-ones and quinoxalin-2,3-diones. These derivatives are particularly interesting since some of them showed antimicrobial (against several bacteria, viruses, fungi, etc), or anticancer activities. Furthermore, others are reported to be potent no-NMDA glutamate receptor antagonists, endowed with anxiolytic, deconditioning, analgesic, antispastic, antiallergic, antithrombotic activities. In this article we also report SAR studies and the most important methods of synthesis of the quinoxalin-2(3)-(di)ones.

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Section: Reactions Of Quinoxalin-2-onesmentioning

confidence: 99%

Section: Reactions Of Quinoxalin-2-onesmentioning

confidence: 99%

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Carta

Piras²,

Loriga

et al. 2006

MRMC

221

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“…These values agree with a previous report, which established that for a series of styryl‐ benzodiazinones, the maxima of absorption are in the range 390–450 nm for polar solvents. In particular the compound here called Me 2 NSQx depicted an absorption maximum at 446 nm in ethanol …”

Section: Resultsmentioning

confidence: 99%

Modulation of Lactam‐Lactim Tautomerism of Quinoxalin‐2‐one Induced by Cucurbit[7]uril: A Comparative Study with Oxazin‐2‐one

et al. 2018

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The formation of inclusion complexes between cucurbit[7]uril (CB7) and N,N‐(dimethylamino)styrylquinoxalin‐2‐one (Me2NSQx) or the N,N‐(dimethylamino)styryloxazin‐2‐one (Me2NSOxa) dyes, was carried out using spectroscopy techniques (UV‐vis, fluorescence and NMR), flash photolysis, mass spectrometry and docking studies. Results show that: (i) both dyes form inclusion complexes with a CB7 excess, which depicts huge bathochromic shifts (>100 nm); (ii) Me2NSQx and Me2NSOxa, firstly form a 1:1 complex and at higher CB7 concentrations, a 2:1 host:guest complex is generated; (iii) the inclusion complex for Me2NSQx changes from its stable lactam form to the lactim tautomer, while for Me2NSOxa the equilibrium is shifted to the oxazinium tautomer. Finally, in the case of Me2NSQx dye, spectroscopic and docking studies indicate that the most stable complex is Me2NSQx@CB7 (1:2) in its lactim form, while in Me2NSOxa the equilibrium is shifted to the oxazinium containing complex. Therefore, our results evidence the importance of the interaction of CB7 as another form of controlling the tautomerism equilibrium of lactam or lactones derivatives.

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“…12, the increase in the quantum yield of fluorescence upon complexation of crown-containing styrylbenzodiazinone was attributed to the fact that the metal cation prevents transition of the excited molecule to a twisted state with the charge transfer (the TICT state). Generally, the opposite effect is observed for styryl compounds containing benzocrown Lls or N-phenylaza-crown t6 fragments, although there are exceptions to this rule.…”

Section: C2h Smentioning

confidence: 99%

Crown-containing styryl dyes

et al. 1997

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Complexation of styryl dyes containing the N-phenylaza-I5-crown-5 fragment (trans-2a,h) with Ca 2. ions in MeCN was studied. Unlike cationic dye trans-2a, betaine trans-2b forms both complexes of t : I stoichiometo' and aggregates consisting of four dye molecules and one Ca 2" ion. Cation-induced aggregation was observed also for the analog of dye trans-2b, which contains a dimethyiamino group instead of an azacrown ether fragment (trans-3). Apparently, the interaction between a metal cation and sulfo groups of molecules trans-2b or trans-3 makes the main contribution to the stability of aggregates. The dependence of the stability of aggregates on the nature of the metal cation was studied.Macrocycfic compounds, which are capable of binding metal cations selectively and absorbing light in the visible region, can be used as reagents for colorimetric or luminescent determination of metal cations z and as elements of photoswitched molecular systems, z,3Previously, we synthesized a number of styryl dyes trans-la~d containing a 15-crown-5 fragment. 4,5 %,.)trans-1 a---d

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Styrylbenzodiazinones 1. Synthèse, structure et propriétés photophysiques

Cited by 17 publications

References 4 publications

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Modulation of Lactam‐Lactim Tautomerism of Quinoxalin‐2‐one Induced by Cucurbit[7]uril: A Comparative Study with Oxazin‐2‐one

Crown-containing styryl dyes

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