Studies in synthesis of new psoralenamines

Patel, J. M.; Soman, Shubhangi S.

doi:10.1002/jhet.327

Cited by 5 publications

(5 citation statements)

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“…The starting materials 7-hydroxy-4methyl-2H-chromen-2-one (1) 22 , 4-methyl-7-(2oxopropoxy)-2H-chromen-2-one (2) 23 , 4substituted-3-thiosemicarbazides (3a-d) 24 , and phenacyl bromides (5a-e) 25 ; were synthesized according to reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

“…The starting material 4-methyl-7-(2oxopropoxy)-2H-chromen-2-one (2) was prepared according to a reported procedure through reaction of 7-hydroxy-4-methyl-2Hchromen-2-one (1) with chloroacetone in the presence of anhydrous potassium carbonate using acetone as a solvent 25 . Structure of compound 2 was confirmed by comparison of its physical and spectral data with the reported ones 25 . 1 H NMR spectrum of compound 2 showed two singlets at δ 2 and 2.10 ppm (two methyl groups), singlet at δ 4.9 ppm (OCH 2 ), singlet at δ 6.3 ppm (C-H 3 of coumarin ring) besides multiplet (2H) at 6.8-7.3 ppm corresponding to C-H 6 and C-H 8 of coumarin, in addition to a doublet (1H) at 7.4-7.6 ppm corresponding to C-H 5 coumarin.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Biological Evaluation of Some New Coumarin Derivatives as Antimicrobial Agents

Youssif

2013

Bulletin of Pharmaceutical Sciences. Assiut

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The purity of all new compounds was checked by TLC and elucidation of their structures was confirmed by IR, 1 H NMR, and mass spectrometry along with elemental microanalyses. All the target compounds were evaluated for their possible antimicrobial activity. Most of the tested compounds showed weak to moderate antibacterial activity against most of the bacterial strains used in comparison with gatifloxacin as a reference drug. The most active compounds were 6b, 6c, 7b, 8b, 8c, and 9c against B. cereus, E. coli and S. marcescens. Results of antifungal activity revealed that all compounds showed weak to moderate activity against S. brevicaulis, while ketoconazole as a reference drug was completely inactive . Compounds 6a, 6b, 6c, 6e and 7b were even more active than ketoconazole against F. oxysporum.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Biological Evaluation of Some New Coumarin Derivatives as Antimicrobial Agents

Youssif

2013

Bulletin of Pharmaceutical Sciences. Assiut

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“…Наступними об'єктами дослідження були фурокумарини 18a-d. Дані сполуки легко синтезувати з 7-гідрокси-4-метилкумарину 19 за методом Робінсона [17][18][19][20], а саме: алкілюванням гідроксигрупи -галогенокетонами та наступним замиканням фуранового циклу в сильно лужному середовищі (рис. 6).…”

Section: рис 4 3-гетарилкумарини та їх 2-імінопохідні в реакції вілunclassified

“…Вихідні сполуки синтезовані за методиками, наведеними в наступних джерелах: сполука 16а - [13], 16b - [12], 18a - [17], 18b - [18], 18c - [19], 18d - [20], 23 - [25]. 3-(2,4-Біс(2-етокси-2-оксоетокси)-5-(1-оксо-1H-ізохромен-3-іл)феніл)бут-2-енова кислота (25).…”

Section: рис 7 синтез амідів 3-(3-r-6-алкоксибензофуран-5-іл)акрилоunclassified

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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