Preliminary Evaluation of Antimicrobial Activity of Diastereomeric cis/trans-3-Aryl(Heteroaryl)-3,4-dihydroisocoumarin-4-carboxylic Acids

Abstract

Preliminary differentiating screening of the antibacterial and antifungal activity of a series of diastereomeric cis/trans-3-aryl(heteroaryl)-3,4-dihydroisocoumarin-4-carboxylic acids (3a- i) was performed by the agar diffusion method against twelve microorganism strains of different taxonomic groups. S. aureus and A. niger were the most sensitive strains to the antibiotic effect of the tested compounds, both inhibited by 10 of 12 compounds. The most potent antibacterial agent was cis-3-phenyl-3,4-dihydroisocoumarin-4-carboxylic acid (cis-3a), exhibiting activity against all seven bacterial test strains

Methyltrans-6-oxo-11-thiophen-2-yl-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylate

“…The systematic studies on the synthesis of new heterocyclic compounds with expected pharmacological activities on the basis of homophthalic anhydride carried out in our laboratory (Haimova et al, 1977;Kozekov et al, 2002;Stoyanova et al, 2003) focused our attention on some isochroman-1-one derivatives Bogdanov et al, 2005). Thus, we have isolated the title compound (I) as a by-product of a reaction between homophthalic anhydride and thiophene-2-carbaldehyde in pyridine.…”

(S)-Methyl 2-[(3R,4R)-2-benzyl-3-(2-furyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamido]-3-(1H-indol-3-yl)propanoate

“…Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999). As a part of our studies on the synthesis of new heterocyclic compounds with expected pharmacological activities carried out in our laboratory (Bogdanov et al, 2007;Burdzhiev & Stanoeva, 2006;Kandinska et al, 2006) we focused our attention to some 3,4-dihydroisoquinolin-1-ones, containing amino acid moieties. The title compound (I) was synthesized while searching for new ACE inhibitors of this type.…”

Highly Enantioselective Catalytic Kinetic Resolution of α‐Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides

“…We (and others) have reported catalytic asymmetric cycloaddition reactions between homophthalic anhydrides 17 , behaving as nucleophiles, with different electrophiles, for example, aldehydes, ketones, alkylidene oxindoles, imines, and nitrostyrenes . The processes involving aldehydes provide one‐pot access to dihydroisocoumarins, such as 14 (Figure D): core structural units in a range of natural products possessing a diverse array of medicinally relevant biological activities, for instance: cytotoxic/antiproliferative, antimicrobial, antifungal, antiulcer, antimalarial, anti‐inflammatory, antioxidant and antiallergic properties. A weakness associated with these methodologies is that they provide no catalytic access to dihydroisocoumarins incorporating a stereocentre adjacent to the lactone core—a feature of a number of structurally important natural products, such as the potent respiratory chain inhibitor Ajudazol A ( 15 ) and the recently discovered highly active herbicide Bacilosarcin ( 16 , Figure D) .…”