6-Substituted 2-Oxo-2h-1-Benzopyran-3-Carboxylic Acid Derivatives in a New Approach of the Treatment of Cancer Cell Invasion and Metastasis

in European Journal of Medicinal Chemistry (2008), 43(12), 2735-50

Novel 6-substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives were synthesized and their potency in reducing the invasive behaviour of HT 1080 fibrosarcoma cells was evaluated. Structure ... [more ▼]

Novel 6-substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives were synthesized and their potency in reducing the invasive behaviour of HT 1080 fibrosarcoma cells was evaluated. Structure-activity relationships were deduced from biological results and will be used in further design of new active compounds. In particular, the acetoxymethyl substituent found at the 6-position of previously described active compounds can be replaced by an acetamidomethyl substituent without loss of potency; while the presence of an aryl ester function at the 3-position was preferred to a thioester or an amide function to induce marked biological activity. This work confirms the interest of aryl esters of 6-substituted coumarin-3-carboxylic acids as potential new anti-cancer agents. [less ▲]

Evaluation pharmacologique du 6-acétoxyméthyl-2-oxo-2H-1-benzopyrane-3-carboxylate de 3-bromophényle en tant qu’agent anti-angiogénique

Poster (2005, May)

Effects of recently developed 6-substituted 3-bromophenyl 2-oxo-2H-1-benzopyran-3-carboxylate derivatives on HT1080 cell invasion in vitro

in Fundamental & Clinical Pharmacology (2004)

Effects of recently developed 6-substituted 3-bromophenyl 2-oxo-2H-1-benzopyran-3-carboxylate derivatives on HT1080 cell invasion in vitro

Poster (2003, November 22)

3-Bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo

in British Journal of Cancer (2003), 88(7), 1111-1118

In search for new anticancer agents, we have evaluated the antiinvasive and antimigrative properties of recently developed synthetic coumarin derivatives among which two compounds revealed important ... [more ▼]

In search for new anticancer agents, we have evaluated the antiinvasive and antimigrative properties of recently developed synthetic coumarin derivatives among which two compounds revealed important activity: 3-chlorophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate and 3-bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate, Both drugs were able to inhibit cell invasion markedly in a Boyden chamber assay, the bromo derivative being more potent than the reference matrix metalloprotease (MMP) inhibitor GI 129471. In vivo, tumour growth was reduced when nude mice grafted with HT 1080 or MDA-MB231 cells were treated i.p. 3 days week(-1) with the bromo coumarin derivative. These effects were not associated with the inhibition of urokinase, plasmin, MMP-2 or MMP-9. The mechanism of action of the drugs remains to be elucidated. However, these two coumarin derivatives may serve as new lead compounds of an original class of antitumour agents. [less ▲]

Les esters du 6-hydroxymethyl-2-oxo-2H-1-benzopyrane-3-carboxylate de 3-bromophényle inhibent l’invasion des cellules de fibrosarcome humain in vitro

Poster (2003, January 31)

Investigation of the inhibition mechanism of coumarins on chymotrypsin by mass spectrometry

in Tetrahedron (2003)

Synthèse et évaluation biologique de 2,3-dihydro-4H-1,2,4-pyridothiadiazine 1,1-dioxydes en tant que modulateurs allostériques positifs des récepteurs AMPA

Poster (2002, May)

Les esters du 6-hydroxyméthyl-2-oxo-2H-1-benzopyrane-3-carboxylate de 3-bromophényle en tant qu’agents inhibiteurs de l’invasion cellulaire in vitro

Poster (2002, May)

Effects on in vitro and in vivo cellular invasion of two 6-(acetoxymethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives

Poster (2001, October 16)