Dibenzorhodamine dyes useful as florescent labelling agents

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 491/147 (2006.01) C07D 209/60 (2006.01) C07D 221/10 (2006.01) C07D 311/78 (2006.01) C07D 491/14 (2006.01) C07H 19/04 (2006.01) C07H 19/10 (2006.01) C07H 19/20 (2006.01) C07H 21/00 (2006.01) C09B 11/02 (2006.01) C09B 11/24 (2006.01) C12Q 1/68 (2006.01)

Patent

CA 2311476

Dibenzorhodamine compounds having structure (1) are disclosed, including nitrogen- and aryl-substituted forms thereof. In addition, intermediates useful for synthesizing such compounds are disclosed, such intermediates having structure formula (I). In formula (I), Ri is H or (a) wherein Y is H, lower alkyl, lower alkene, lower alkyne, aromatic, phenyl, polycyclic aromatic, heterocycle, water-solubilizing group, or linking group, including substituted forms thereof. When Ri is H, the C-12-bonded nitrogen and the C-12 and C-13 carbons form a first ring structure having from 4 to 7 members, and/or the C-12-bonded nitrogen and the C-11 and C-12 carbons form a second ring structure having from 5 to 7 members. The compounds of formula (I) further include aryl- and nitrogen-substituted forms thereof. The invention further includes energy transfer dyes comprising the dibenzorhodamine compounds, nucleosides labeled with the dibenzorhodamine compounds, and nucleic acid analysis methods employing the dibenzorhodamine compounds.

L'invention concerne des composés de dibenzorhodamine ayant la structure représentée par la formule (1), y compris les formes à substitution azote et aryle. L'invention concerne également des intermédiaires utiles pour la synthèse desdits composés, ayant la structure formule (I) représentée ci-après. Dans la formule (I), R1 est H ou (a) sachant que Y est H, alkyle inférieur, alcène inférieur, alkyne inférieur, un groupe aromatique, phényle, aromatique polycyclique, hétérocyclique, hydrosoluble ou de liaison, y compris les formes substituées. Lorsque R1 est H, l'azote lié en C-12 et les atomes de carbone C-12 et C-13 forment une première structure cyclique comprenant de 4 à 7 éléments, et/ou l'azote lié en C-12 et les atomes de carbone C-11 et C-12 forment une seconde structure cyclique comprenant de 5 à 7 éléments. Les composés représentés par la formule (I) englobent aussi les formes à substitution azote et aryle. L'invention concerne également des colorants à transfert d'énergie renfermant les composés de dibenzorhodamine considérés, des nucléosides marqués via ces composés, ainsi que des procédés relatifs à l'analyse des acides nucléiques reposant sur l'utilisation desdits composés.

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