Ya. L. Garazd

Neoflavones. 2. Methods for Synthesizing and Modifying 4-Arylcoumarins

Literature data up to 2003 were presented and information on methods for preparing and modifying natural 4-arylcoumarins and their synthetic analogs were systematized.

NEOFLAVONES. 1. NATURAL DISTRIBUTION AND SPECTRAL AND BIOLOGICAL PROPERTIES

Data on neoflavones isolated from 58 plants belonging to the Clusiaceae, Fabaceae, Rubiaceae, Thelypteridaceae, Passifloraceae, Asteraceae, and Rutaceae families from the literature up to 2002 were systematized and reviewed. A list of 131 4-phenylcoumarins with information on the plant sources, structures, physicochemical data, and pharmacological properties with references to the original literature was composed.

Modified Coumarins. 17. Synthesis and Anticoagulant Activity of 3,4-Cycloannelated Coumarin D-Glycopyranosides

Abstract3,4-Cyclocondensed coumarin O-glycopyranosides containing glucose, galactose, xylose, and arabinose were synthesized by condensation of potassium salts of hydroxycoumarins and acetobromosugars. 7-(β-D-Galactopyranosyloxy)-2,3-dihydrocyclopenta[c]chromen-4-one, 3-(β-D-xylopyranosyloxy)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one, and 3-(α-D-arabinopyranosyloxy)benzo[c]chromen-6-one exhibited distinct anticoagulant activity.

MODIFIED COUMARINS. 6. SYNTHESIS OF SUBSTITUTED 5,6-BENZOPSORALENS

Substituted 5H-benzo[c]furo[3,2-g]chromen-5-ones, modified analogs of psoralen that contain a benzene ring annelated at the 5,6-position of a furo[3,2-g]chromen-7-one system, were synthesized from 3-hydroxy- 6H-benzo[c]chromen-6-ones.

Synthesis of amino-acid derivatives of chrysin

Various conjugates of amino acids with chrysin in which the amino acid was bonded through the C- or N-terminus to the flavone were prepared using peptide chemistry methods (symmetric anhydrides and activated esters).

Natural Dibenzo[b,d]Pyran-6-Ones: Structural Diversity and Biological Activity

Natural dibenzo[b,d]pyran-6-ones are common and structurally diverse secondary metabolites that occur frequently in plants, fungi, lichens, and animal waste and possess broad spectra of biological activities such as cytotoxic, antioxidant, antifungal, and antimicrobial. The literature on the isolation, structural diversity, and biological activity of natural dibenzo[b,d]pyran-6-ones from 1949 to December 2014 was reviewed.

Modified Coumarins. 12. Synthesis of 3,4-Cycloannelated Coumarin β-D-Glucopyranosides

O-β-D-Glucopyranosides were synthesized using 3,4-cycloannelated hydroxycoumarins as aglycons. Phenolic hydroxyls were O-glycosylated via condensation of coumarin potassium salts with acetobromoglucose in homogeneous medium and in a liquid-liquid system using a phase-transfer catalyst.

MODIFIED COUMARINS. 29. SYNTHESIS OF STRUCTURAL ANALOGS OF NATURAL 6-ARYLFURO(3,2-g)CHROMEN-7-ONES

3-Substituted 6-arylfuro[3,2-g]chromen-7-ones, structural analogs of natural furocoumarins, were synthesized by linear annelation of a furan fragment to a 3-arylcoumarin system.

Modified coumarins. 26. Synthesis of angular dihydrooxazinocoumarins from 3-hydroxy[b,d]pyran-6-one

N-Substituted angular pyranodihydrobenzoxazines were prepared by condensation of 3-hydroxy-dibenzo[b,d]pyran-6-one with various primary amines and two equivalents of formaldehyde in the presence of 4-N,N-dimethylaminopyridine as base.

Modified Coumarins. 4. Synthesis and Biological Properties of Cyclopentaneannelated Furocoumarins

Psoralen and allopsoralen analogs that contain an annelated cyclopentane were synthesized from 7-hydroxyand 9-hydroxy-1,2,3,4-tetrahydrocyclopenta[c]chromen-4-ones. 9-Phenyl-1,2,3,4-tetrahydrocyclopenta[c]furo[3,2-g]chromen-4-one exhibited low toxicity, acted as a CNS stimulant, and exhibited cardiotropic activity.