Ph-responsive fluorescent false neurotransmitters and their use
AssigneeThe Trustees of Columbia University in the City of New York
InventorsDalibor Sames, David Sulzer, Minhee Lee, Niko Gubernator
Life of this patent
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Abstract
This invention relates to compounds having the following structure: wherein Y is O, X is O, bond α is absent and bond β is present, or Y is H, X is CH, bond α is present, and bond β is absent; atom Z is a carbon and bonds χ, δ and γ are present, or atom Z is a nitrogen and bonds χ, δ and γ are absent, or atom Z is a nitrogen and bonds χ and δ are present and γ is absent. R1, R2, R3, R4, R5, and R6 are various substituents as described in the specification.
Claims25
A compound having the following structure:
- wherein
- Y is O, X is O, bond α is absent and bond β is present, or
- Y is H, X is CH, bond α is present, and bond β is absent;
- atom Z is a carbon and bonds χ, δ and γ are present, or atom Z is a nitrogen and bonds χ, δ and γ are absent, or
- atom Z is a nitrogen and bonds χ and δ are present and γ is absent;
- R1 is —OH, —O—R7, or —O−,
- wherein R7 is alkyl, alkenyl or alkynyl;
- R2 is —H, halogen, alkyl, alkenyl, alkynyl;
- R3 is —H, —OH, alkyl, alkenyl, alkynyl, or halogen;
- or
- R1 is H, and R2 together with R3 form a substituted or unsubstituted aromatic ring;
- R4 is —H, —CH2CH2NH2, or —CH2CH2N(R8)2:
- wherein R8 is alkyl, alkoxycarbonyl, alkenyl, or alkynyl;
- R5 is —H, —CH2CH2NH2, or —(C═O)CH2CH2NH2, —CH2CH2N(R9)2;
- wherein R9 is alkyl, alkoxycarbonyl, alkenyl, or alkynyl;
- and
- R6 is H, alkyl, alkenyl, alkynyl, or halogen;
- wherein each occurrence of alkyl, alkoxy, alkenyl, or alkynyl is substituted or unsubstituted, straight chain or branched,
- or a pharmaceutically acceptable salt thereof.
A process for preparing a compound having the structure
- wherein
- Y is O, X is O, bond α is absent and bond β is present, or
- Y is H, X is CH, bond α is present, and bond β is absent;
- atom Z is a carbon and bonds χ, δ and γ are present, or atom Z is a nitrogen and bonds χ, δ and γ are absent, or
- atom Z is a nitrogen and bonds χ and δ are present and γ is absent;
- R1 is —OH, —O—R7, or —O−,
- wherein R7 is alkyl, alkenyl or alkynyl;
- R2 is —H, halogen, alkyl, alkenyl, alkynyl;
- R3 is —H, —OH, alkyl, alkenyl, alkynyl, or halogen;
- or
- R1 is H, and R2 together with R3 form a substituted or unsubstituted aromatic ring;
- R4 is —H, —CH2CH2NH2, or —CH2CH2N(R8)2;
- wherein R8 is alkyl, alkoxycarbonyl, alkenyl, or alkynyl;
- R5 is —H, —CH2CH2NH2, or —(C═O)CH2CH2NH2, —CH2CH2N(R9)2;
- wherein R9 is alkyl, alkoxycarbonyl, alkenyl, or alkynyl;
- and
- R6 is H, alkyl, alkenyl, alkynyl, or halogen;
- wherein each occurrence of alkyl, alkoxy, alkenyl, or alkynyl is substituted or unsubstituted, straight chain or branched, comprising:
- a) contacting a compound having the structure
- with a compound having the structure
- wherein R10 is —OH, alkoxy, alkenyloxy, alkynyloxy, aryloxy, halogen, or heteroaryl,
- wherein each occurrence of alkoxy, alkenyloxy, alkynyloxy, aryloxy, and heteroaryl is substituted or unsubstituted;
- or
- a′) contacting a compound having the structure
- with a compound having the structure
- wherein R11 is —OH, alkoxy, alkenyloxy, alkynyloxy, aryloxy, halogen, or heteroaryl;
- R12 and R13 are each H or together form ═O;
- n is 1 or 2;
- wherein each occurrence of alkoxy, alkenyloxy, alkynyloxy, aryloxy, and heteroaryl is substituted or unsubstituted;
- to form a compound having the structure
- b′) contacting the compound formed in step a′) with a suitable base;
- so as to prepare the compound.
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Dependencies are inferred from the claim text.