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US 2006/0040908 A1Published application
Novel chalcogenoxanthylium dyes for purging blood pathogens and for photodynamic therapy
AssigneeThe Research Foundation of State University of New York
InventorsMichael Detty, David Donnelly, Stephen Wagner
Life of this patent
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Abstract
Provided are chalcogenoxanthylium compounds which can effectively be used as sensitizers in photodynamic therapy, virucides in photodynamic antimicrobial chemotherapy and reversal agents of Pgp function in cancer cells. Further provided is a general method for the preparation of chalcogenoxanthylium compounds.
Claims20
1) A compound having the structure of Formula I:
- wherein E is S or Se and A− is an anionic group selected from the group consisting of halides, sulfonates;
- carboxylates;
- hexafluorophosphate, and tetrafluoroborate;
- and
- I)
- i) W, X, Y, and Z are hydrogen;
- ii) R1′, R2′, R1″ and R2″ are independently hydrogen or C1 through C8 branched or unbranched alkyl, and, optionally,
- 1) R1′ and R2′ are alkyl groups connected such that they comprise a 3-, 4-, 5-, 6- or 7-membered ring
- which, optionally, bears alkyl or aryl substituents;
- and/or
- 2) R1″ and R2″ are alkyl groups connected such that they comprise a 3-, 4-, 5-, 6- or 7-membered ring
- which, optionally, bears alkyl or aryl substituents;
- iii) R is hydrogen or a C1 through C8 alkyl, aryl, heteroaryl, substituted aryl or substituted heteroaryl group;
- wherein if E is S, R is not a 2-substituted phenyl group bearing groups in the 2-position of the following form:
- —CO2H, —CO2R4, or
- wherein R4 and R5 are C1 through C8 alkyl groups;
- and
- wherein if E is Se, R is not hydrogen;
- or
- II)
- i) W, X, Y and Z are independently hydrogen or C1 through C8 alkyl;
- ii) R1′, R2′, R1″ and R2″ are independently hydrogen or C1 through C8 alkyl, and wherein
- R1′ and Y are connected such that they comprise a five, six or seven-membered ring
- or
- and/or R2′ and Z are connected such that they comprise a five-, six- or seven-membered ring
- and/or R1″ and W are connected such that they comprise a five-, six- or seven-membered ring
- and/or R2″ and X are connected such that they comprise a five-, six- or seven-membered ring:
- and
- iii) R is a C1 through C8 alkyl, aryl, substituted aryl, heterocyclic or substituted heterocyclic group.
26 more elements
11) A method for the preparation of a compound, said method comprising the steps of:
- a) providing a compound (1) of the following structure:
- wherein
- I)
- i) Y and Z are hydrogen;
- ii) R1′ and R2′, are independently hydrogen or C1 through C8 branched or unbranched alkyl and, optionally, R1′ and R2′ are alkyl groups connected such that they comprise a three, four, five, six or seven-membered ring,
- which, optionally, bears alkyl or aryl substituents;
- or
- II)
- i) Y and Z are independently hydrogen or C1 through C8 alkyl and R1′ and R2′ are independently hydrogen or C1 through C8 alkyl;
- wherein R1′ and Y are connected such that they comprise a five, six or seven-membered ring:
- and/or R2′ and Z are connected such that they comprise a five-, six- or seven-membered ring:
- b) forming a reaction mixture comprising said compound (1), N,N,N,N-tetramethylethylenediamine (TMEDA), tert-butyl lithium and a solvent whereby said compound (1) is lithiated at the 2 position;
- c) adding a compound of the following structure:
- to the reaction mixture such that a compound (3),
- is formed;
- wherein E is S or Se, and
- I)
- i) W and X are hydrogen;
- ii) R1″ and R2″ are independently hydrogen, C1 through C8 branched or unbranched alkyl and, optionally, R1″ and R2″ are alkyl groups connected such that they comprise a five, six or seven-membered ring:
- which, optionally bears alkyl or aryl substituents;
- or
- II)
- i) W and X are independently hydrogen or C1 through C8 alkyl;
- ii) R1″ and R2″ are independently hydrogen or C1 through C8 alkyl, and
- wherein R1″ and W are connected such that they comprise a five, six or seven-membered ring:
- and/or R2″ and X are connected such that they comprise a five-, six- or seven-membered ring:
- d) contacting said compound (3) with lithium diisopropylamide (LDA) such that a compound (4) of the following structure is formed:
- e) converting compound (4) to a compound (5) of the following structure:
25 more elements
Dependencies are inferred from the claim text.