3-(2-Quinolyl)- and 3-(5-carbethoxyfuryl-2)coumarins

Shablykina, O. V.; Khilya, O. V.; Ishchenko, V. V.; Khilya, V. P.

doi:10.1007/s10600-005-0198-4

Cited by 4 publications

(6 citation statements)

References 3 publications

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“…Sulfonamides 4 were synthesized in an acetonitrile solution in the presence of pyridine as a base (Scheme 2). Previously, we obtained similar sulfamides in 1,4-dioxane with Et3N as a base [6,7]. It is worth noting that both methods are equally effective to synthesize amides with excellent yields.…”

Section: Resultsmentioning

confidence: 97%

“…Yield: 5.63 g, 78%. (Alternative procedure of sulfonyl chloride 2 obtaining as well as spectra data was also described in [6]).…”

Section: Synthesis 4-(1-oxo-1h-isochromen-3-yl)benzenesulfonyl Chlori...mentioning

confidence: 99%

“…Previously, we presented a method for constructing sulfonamides based on 3-phenylisocoumarin 1 (Scheme 1) by chlorosulfonation and subsequent reaction of the resulting sulfochloride 2 with amines [6,7]. In this communication we describe a synthesis of new derivatives of isocoumarin 1 and a preliminary assessment of their anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

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4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect on cancer cell growth

2021

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Sulfonamide derivatives of 3-phenyl-1H-isochromen-1-one were synthesized by reaction of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride with amines. The specific parameters of chlorosulfonation of 3-phenyl-1H-isochromen-1-one have been identified; the procedure for synthesis of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride and its by-product (disulfochloride) was optimized. The evaluation of anticancer activity of obtained sulfonamides showed no appreciable cytotoxicity

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Section: Resultsmentioning

confidence: 97%

“…Yield: 5.63 g, 78%. (Alternative procedure of sulfonyl chloride 2 obtaining as well as spectra data was also described in [6]).…”

Section: Synthesis 4-(1-oxo-1h-isochromen-3-yl)benzenesulfonyl Chlori...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect on cancer cell growth

2021

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“…There are known synthesis pathways for 2-quinolyl coumarins [ 34 , 35 , 36 , 37 ], but our reaction ( Scheme 5 ) provides a more convenient alternative synthetic route. The reaction was further tested for functionalised aromatic aldehydes such as 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 4-Hydroxyquinolines as Potential Cytotoxic Agents

Csuvik

Szemerédi

Spengler

et al. 2022

IJMS

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The synthesis of alkyl 2-(4-hydroxyquinolin-2-yl) acetates and 1-phenyl-4-(phenylamino)pyridine-2,6(1H,3H)-dione was optimised. Starting from 4-hydroxyquinolines (4HQs), aminomethylation was carried out via the modified Mannich reaction (mMr) applying formaldehyde and piperidine, but a second paraformaldehyde molecule was incorporated into the Mannich product. The reaction also afforded the formation of bisquinoline derivatives. A new 1H-azeto [1,2-a]quinoline derivative was synthesised in two different ways; namely starting from the aminomethylated product or from the ester-hydrolysed 4HQ. When the aldehyde component was replaced with aromatic aldehydes, Knoevenagel condensation took place affording the formation of the corresponding benzylidene derivatives, with the concomitant generation of bisquinolines. The reactivity of salicylaldehyde and hydroxynaphthaldehydes was tested; under these conditions, partially saturated lactones were formed through spontaneous ring closure. The activity of the derivatives was assessed using doxorubicin-sensitive and -resistant colon adenocarcinoma cell lines and normal human fibroblasts. Some derivatives possessed selective toxicity towards resistant cancer cells compared to doxorubicin-sensitive cancer cells and normal fibroblasts. Cytotoxic activity of the benzylidene derivatives and the corresponding Hammett–Brown substituent were correlated.

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“…Раніше нами було синтезовано досить великий масив 3-(гет)арилкумаринів загальної формули 12 (рис. 4) та їх алкоксипохідних 13 [12][13][14], що цікавили нас передусім своїми спектральними характеристиками [15]. Перетворення 12  13 відбувалось у ацетоні (рідше -у ДМФА), переважно з високими виходами, і розкриття лактонової системи у жодному із випадків не було зафіксовано.…”

Section: рис 3 одержання практично значущих похідних о-алкоксикоричunclassified

CERTAIN CASES OF o-ALKOXYCINNAMIC ACIDS CREATION FROM COUMARINS IN O-ALKYLATION CONDITION

2019

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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A number of new derivatives of o-alkoxy cinnamic acids were obtained from various coumarins by opening the lactone fragment and O-alkylation of the endocyclic Oxygen atom. The α-hetaryl-β-(2-alkoxy-5-chlorophenyl)cinnamic acids were obtained from 3-(benzothiazol-2-yl)-6-chlorocoumarin and 3-(benzimidazol-2-yl)-6-chlorocoumarin by treatment with diluted alkali followed by p-methylbenzyl chloride or dimethyl sulfate addition, respectively. A similar reaction stages (opening in aqueous alkali and alkylation of the phenolate anion) was applied to the synthetic analogues of psoralen – 5-methylfuro[3,2-g]coumarins with various substituents in the furan fragment. Thus it was possible to obtain a number of 3- and 4-substituted 3-(6-alkoxybenzofuran-5-yl)but-2-enoic acids. But in this case, the conversion of the starting furo[3,2-g]coumarins to cinnamic acid derivatives was not complete even after long time of reaction with a big excess of an alkylation agent. Therefore, the necessary step is the separation of the target acid from unreacted coumarin by dissolving the product in a saturated NaHCO3 solution. The insoluble part is a practically pure starting material, which can be recycled in the reaction; so the total yield of the product would be increased. To demonstrate the synthetic abilities of 3-(6-alkoxybenzofuran-5-yl)but-2-enoic acids these compounds were used in synthesis of amides with pharmacophore fragments: a phenethylamine derivative with an additional sulfamide group and a β-alanine derivative. The experiments showed that the 3-azolylcoumarins and furo[3,2-g]coumarins coumarin cycle's opening occurs only in aqueous alkali, and when alkylated in an organic solvent in the presence of K2CO3, the lactone fragment remains unchanged. The 7-hydroxy-6-(isocoumarin-3-yl)-4-methylcoumarin cycle turned out to be more labile. The result of alkylation of this compound with ethyl acetate of chloroacetic acid in the presence of K2CO3 depended on the nature of the aprotic solvent and the temperature of reaction. So, when this reaction was carried out in boiling acetone, only the free hydroxyl group at position 7 of coumarin was alkylated. But when the initial coumarin was heated at 100°С with an excess of an alkylating agent in DMSO, simultaneous alkylation of both the free 7-OH group and the endocyclic Oxygen atom occurred.

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3-(2-Quinolyl)- and 3-(5-carbethoxyfuryl-2)coumarins

Cited by 4 publications

References 3 publications

4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect on cancer cell growth

4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect on cancer cell growth

Synthesis of 4-Hydroxyquinolines as Potential Cytotoxic Agents

CERTAIN CASES OF o-ALKOXYCINNAMIC ACIDS CREATION FROM COUMARINS IN O-ALKYLATION CONDITION

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