Aminoacridines

Adcock, B.

doi:10.1002/9780470186596.ch3

Cited by 4 publications

(2 citation statements)

References 113 publications

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“…However, for the exchangeable NH protons, divergence from the correlation line was noticeable; in concert with our previous findings the N-10' atom of the acridinyl moiety present in 3e – h is well known [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ] to have a strong propensity to retain a proton, i.e. the HN-10' tautomer (a 9',10'-dihydroacridine structure, see Figure 1 ) is expected to dominate the tautomeric equilibrium in the subseries.…”

Section: Resultssupporting

confidence: 86%

“…The reaction proceeded regioselectively with only attack by N-2 of (acridin-9-yl)hydrazine observed. As anticipated [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ], 10 also adopted a 9',10'-dihydro-acridine structure (the HN-10' tautomer, Scheme 5 ) as clearly evidenced by the diagnostically shielded signals of C-4' (116.8 ppm) and C-5' (118.3 ppm) [ 17 , 18 ].…”

Section: Resultsmentioning

confidence: 58%

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Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Tomascikova¹,

Imrich²,

Danihel³

et al. 2008

Molecules

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A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including four new compounds, were prepared in order to study substituent effects on cyclization reactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethyl acetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation under alkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f was also prepared. Altogether, twenty new compounds characterized and identified by IR, UV, 1H, 13C and 2D NMR and quantum chemical calculations are described. The tautomerism of the products and regioselectivity of the reactions were evaluated. Compounds 3f–h, 3h∙2HCl, 7b,d and 10 were screened for cytotoxic activity against the L1210 leukemia cell line and all compounds, except for 3f, exhibited promising inhibitions of cell growth.

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Section: Resultssupporting

confidence: 86%

Section: Resultsmentioning

confidence: 58%

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Tomascikova¹,

Imrich²,

Danihel³

et al. 2008

Molecules

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Tautomerism, regioisomerism, and cyclization reactions of acridinyl thiosemicarbazides

Klika

Balentová

Pihlaja

et al. 2006

Journal of Heterocyclic Chem

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The regioselectivities of methyl-and phenylhydrazine with acridin-9-yl isothiocyanate (thus yielding thiosemicarbazides with acridine substituted on the urea-type side) were examined. Methylhydrazine regioselectivity was high with the -nitrogen atom overwhelmingly more nucleophilic than the -nitrogen atom; phenylhydrazine regioselectivity was poor but varied with the solvent and only in the case of ethanol was nucleophilic predominance of the -nitrogen atom pronounced. Of note, whilst both phenyl thiosemicarbazides were present in solution only as spiro forms, the methyl product was present as an equilibrium mixture of open-chain and spiro thiosemicarbazides. Reactions on the NH 2 blocked analogue of methyl acridin-9-ylthiosemicarbazide (1-isopropylidene-2-methylthiosemicarbazide) were also examined. Interestingly, present in the starting material itself was a structural motif of novelty wherein a triazolethione represented the major species of an equilibrium between cyclic and open-chain forms.

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Spectroscopic, structural and theoretical studies of novel, potentially cytotoxic 4-acridonecarboxamide imines

Fröhlichová¹,

Imrich²,

Danihel³

et al. 2009

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Aminoacridines

Cited by 4 publications

References 113 publications

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Tautomerism, regioisomerism, and cyclization reactions of acridinyl thiosemicarbazides

Spectroscopic, structural and theoretical studies of novel, potentially cytotoxic 4-acridonecarboxamide imines

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