Meso-monoiodo-substituted tetramacrocyclic compounds and...

C - Chemistry – Metallurgy – 07 – F

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C07F 3/06 (2006.01) C07D 487/22 (2006.01) C07D 519/00 (2006.01) C07F 1/08 (2006.01) C07F 5/00 (2006.01) C07F 7/00 (2006.01) C07F 13/00 (2006.01) C07F 15/04 (2006.01) C07H 15/26 (2006.01) C07J 43/00 (2006.01)

Patent

CA 2205366

A meso-monoiodo-substituted tetramacrocyclic compound having formula (I), wherein: each of A through D is independently a 5-membered, nitrogen- containing ring having the members necessary to compmlete a porphyrin, chlorin, bacteriochlorin or isobacteriochlorin nucleus; R1 through R8 are independently a hydrogen atom, a lower alkyl group, a lower alkyl carboxylic acid or acid ester group, keto, hydroxy, nitro, amino, or a group that, taken together with another ring, ring substituent or meso-substituent, forms a fused 5- or 6-membered ring; and each of S1 through S3 is H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring. A method for synthesizing the compound comprises the step of iodinating a corresponding unhalogenated, de-metallated tetramacrocyclic compound, followed by metallating. The compound of the invention is an intermediate capable of coupling with an alkyne to achieve a desired mono-meso-alkynyl compound.

Composé tétramacrocyclique à substitution méso-monoiodo de la formule (I), dans laquelle chaque symbole de A à D représente un cycle à 5 chaînons contenant de l'azote et renfermant les chaînons nécessaires pour compléter un noyau porphyrine, chlorine, bactériochlorine ou isobactériochlorine; R¿1? à R¿8? représentent indépendamment un atome d'hydrogène, un groupe alkyle inférieur, un groupe ester d'acide ou d'acide carboxylique d'alkyle inférieur, céto, hydroxy, nitro, amino ou un groupe qui, avec un autre cycle, substituant ou mésosubstituant de cycle, forme un cycle fusionné à 5 ou 6 chaînons; et chaque symbole de S?1¿ à S?3¿ représente H, alkyle substitué ou non substitué, cycloalkyle substitué ou non substitué, un cycle aromatique éventuellement substitué, ou un hétérocycle éventuellement substitué. Un procédé de synthèse du composé consiste à ioder un composé tétramacrocyclique non halogéné et démétallaté, suivi d'une métallation. Le composé selon l'invention est un intermédiaire capable d'être couplé à un alcyne pour produire un composé mono-méso-alcynyle requis.

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