Reduction of 3-(carboxyaryl)isocoumarins with sodium borohydride

Ishchenko, V. V.; Voevoda, N. M.; Shablykina, O. V.; Туров, А. В.; Khilya, V. P.

doi:10.1007/s10593-012-0896-3

Cited by 6 publications

(6 citation statements)

References 10 publications

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“…However, we Acid 4 is formed by base-catalysed selfcondensation of AHPA that is well-known in AHPA chemistry [5][6][7][8]. In contrast, formation of diketone 5 was unexpected because only a few examples are known when aliphatic and aromatic carbonyl group of AHPA both attacked one molecule [9].…”

Section: Resultsmentioning

confidence: 99%

The interaction of homophthalic anhydride with (triphenylphosphoranylidene)acetates

2017

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condensation of homophthalic anhydride.In the study of the interaction of homophthalic anhydride and methyl (triphenylphosphoranylidene)-acetate, along with (1-oxo-1H-isochromen-3-yl)acetate obtaining, two minor products -(1,3-dioxo-1,2,3,4-tetrahydronaphthalene-2-yl)acetate and 2-((1-oxo-1H-isochromen-3-yl)methyl)benzoic acid -had been isolated. The action of tert-butyl (triphenylphosphoranylidene)acetate on homophthalic anhydride didn't lead to Wittig reaction; the encumbered ylide demonstrated only its basicity, and products of homophthalic anhydride self-condensation -2-((1-oxo-1H-isochromen-3-yl)methyl)-benzoic acid and 12-hydroxy-5H-dibenzo[c,g]chromen-5-one -were formed. ________________________________________________________________________________

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Section: Resultsmentioning

confidence: 99%

The interaction of homophthalic anhydride with (triphenylphosphoranylidene)acetates

2017

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“…The method for synthesizing 10-12 was published [8] and also gives the yields, melting points, elemental analyses, mass spectra, and PMR spectra of 10 and 12 and their synthetic intermediates 7 and 9. 3080, 3063, 2976, 2924, 2910, 1758, 1730, 1633, 1606, 1564, 1507, 1481, 1430, 1334, 1295, 1267, 1243, 1209, 1145, 1081, 1026, 957, 887, 820, 799 -2-(1-oxo-1H-isochromen-3-yl)phenoxy]acetate (6).…”

Section: Methodsmentioning

confidence: 99%

“…Starting 3-phenyl-3,4-dihydroisocoumarins 10-12 with a hydroxyacetic-acid fragment as a linker for attaching amino acids were synthesized by known methods [8] using an equivalent amount of ethyl chloroacetate instead of methyl bromoacetate as indicated in the article (Scheme 1). Activated esters [9,10] were used as before [1] to attach amino acids to the carboxylic group of 10-12 through an amide bond.…”

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3-Aryl-3,4-Dihydroisocoumarins with Amino-Acid Fragments

et al. 2016

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New amino-acid derivatives of 3-aryl-3,4-dihydroisocoumarins were prepared via acylation of the amine of natural amino acids by phenoxyacetic acids containing 3,4-dihydroisocoumarin substituents on the benzene ring.In continuation of research on new syntheses of isocoumarins modified by natural amino-acid fragments [1], we focused on 3,4-dihydroisocoumarin derivatives mainly because natural compounds with the 1-oxoisochromane core are dominated by saturated species [2]. Dihydroisocoumarins in living subjects can be associated with their unsaturated analogs, e.g., glycosides of dihydrohomalicine and homalicine [3], the aglycons of which are 3-(3-hydroxyphenyl)-3,4-dihydroisocoumarin and 3-(3-hydroxyphenyl)isocoumarin, respectively. According to recent reports [4,5], dihydroisocoumarins are often encountered among compounds produced by fungal microorganisms. Furthermore, ochratoxin A [6] and amicoumacin B [7], two of few known natural isocoumarins with amino-acid fragments, also contain a 3,4-dihydroisocoumarin ring and are characterized by high biological activity.Starting 3-phenyl-3,4-dihydroisocoumarins 10-12 with a hydroxyacetic-acid fragment as a linker for attaching amino acids were synthesized by known methods [8] using an equivalent amount of ethyl chloroacetate instead of methyl bromoacetate as indicated in the article (Scheme 1). Activated esters [9, 10] were used as before [1] to attach amino acids to the carboxylic group of 10-12 through an amide bond. Thus, the acid group to be modified was converted to the N-hydroxysuccinimide (SuOH) ester (Scheme 2).The resulting esters 13-15 reacted with an optically pure natural L-amino acid to give N-acyl amino-acid derivatives 16-18 (Table 1).

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“…The synthesis method, yields, melting points, elemental analyses, and PMR spectra of 7 and 8 were published before [6]. (7).…”

Section: Methodsmentioning

confidence: 99%

“…Herein we present results from modification of homalicin aglycon analogs, i.e., 3-(4-hydroxyphenyl)isocoumarin (5) and 3-(2-hydroxy-5-methylphenyl)isocoumarin (6), at the active hydroxyl by various natural amino acids. The linker was hydroxyacetic acid.…”

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3-Arylisocoumarins with Amino-Acid Fragments

Shilin¹,

Shablykina²,

Ishchenko³

et al. 2014

Chem Nat Compd

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New amino-acid derivatives of 3-arylisocoumarins were prepared via acylation of the amine groups of natural amino acids by phenoxyacetic acids containing an isocoumarin substituent on the benzene ring.Keywords: [4-(1-oxo-1H-isochromen-3-yl)phenoxy]acetic acid, [2-(1-oxo-1H-isochromen-3-yl)-4-methylphenoxy]acetic acid, N-hydroxysuccinimide, activated ester, amino acid.Interest in isocoumarins has risen consistently since the first mention of natural [1] and synthetic [2] compounds with this core because they are widely distributed in nature and possess high biological activity. The variety of modifications of this heterocyclic system was apparent after the isolation and identification of natural isocoumarins and dihydroisocoumarins from plants and microorganisms.Plant isocoumarins can include both simple molecules and complicated polycyclic structures in both the free and bound state. For example, the heterocyclic isocoumarin ring can be found in glycosides [homalicin (1) and dihydrohomalicin (2)] and as amino-acid derivatives of active functional groups such as ochratoxin A (3) [3] and amicoumacin B (4) [4]. The antibacterial and gastric-protection activities of a group of amicoumacins isolated from plant material were especially high [4,5]. This confirmed that research on the design of natural compound analogs that combine an isocoumarin core with an amino acid was important and urgent.Herein we present results from modification of homalicin aglycon analogs, i.e., 3-(4-hydroxyphenyl)isocoumarin (5) and 3-(2-hydroxy-5-methylphenyl)isocoumarin (6), at the active hydroxyl by various natural amino acids. The linker was hydroxyacetic acid.Isocoumarin derivatives 5 and 6 were alkylated by chloroacetic acid ester with subsequent hydrolysis of the ester [6] to obtain 7 and 8 with a carboxylic acid that was capable of reacting with the amino-acid NH 2 group.

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Reduction of 3-(carboxyaryl)isocoumarins with sodium borohydride

Cited by 6 publications

References 10 publications

The interaction of homophthalic anhydride with (triphenylphosphoranylidene)acetates

The interaction of homophthalic anhydride with (triphenylphosphoranylidene)acetates

3-Aryl-3,4-Dihydroisocoumarins with Amino-Acid Fragments

3-Arylisocoumarins with Amino-Acid Fragments

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