Azetidine-substituted fluorescent compounds

Patent metadata

Field	Value
Publication number	US-2019107534-A1
Application number	US-201816211388-A
Country	US
Kind code	A1
Filing date	Dec 6, 2018
Priority date	Apr 1, 2014
Publication date	Apr 11, 2019
Grant date	—

Abstract

The presently-disclosed subject matter includes azetidine-substituted fluorescent compounds, where the compounds may be used as probes, dyes, tags, and the like. The presently-disclosed subject matter also includes kits comprising the same as well as methods for using the same to detect a target substance.

First claim

What is claimed is:

1 . A compound of the formula:

wherein:
each R is independently selected from halogen, H, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 ,CHO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , SO 3 H, and alkyl, alkyl being optionally substituted with one or more heteroatoms independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , and/or SO 3 H;
Q is selected from CR 2 , NR′, O, S, SiR 2 , and Se;
R′ is independently selected from halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , SO 3 H, and alkyl, alkyl being optionally substituted with one or more heteroatoms independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , and/or SO 3 H;
W is selected from C and N;
X is selected from a lone pair of electrons, H, alkyl, aryl, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 ,CHO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , and SO 3 H, X being optionally substituted with one or more heteroatoms independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), C(O)NR 2 , PO 3 H 2 , and/or SO 3 H;
M is selected from CR 2 , C(O), SO 2 , and PO 2 ;
L is selected from O, S, NR, and CN 2 , wherein optionally L and W, taken together with the atoms to which they are bonded, can form a substituted or unsubstituted 5-7 membered ring;
U and V are independently selected from H, alkyl, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , and SO 3 H, alkyl being optionally substituted with one or more heteroatoms independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , and/or SO 3 H, or wherein U and V, taken together with the atoms to which they are bonded, can form a substituted or unsubstituted 5-7 membered ring;
Y is selected from CR 2 , C(O)NR 2 , NR, O, and S; and

Z is selected from H, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , SO 3 H, aryl, and alkyl, alkyl and aryl being optionally substituted with one or more heteroatoms independently selected from N, O, and S, halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO 2 , CHO, COOH, C(O)NR 2 , COO(alkyl), COO(aryl), PO 3 H 2 , and SO 3 H, or wherein Z and Y, taken together with the atoms to which they are bonded, can form a substituted or unsubstituted 5-7 membered ring.

Assignees

• Hughes Howard Med Inst

Inventors

• Lavis Luke D
• Grimm Jonathan B
• Chen Jiji
• Lionnet Timothee
• Zhang Zhengjian
• Revyakin Andrey
• Slaughter Joel

Classifications

• C07D205/06

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• C09B19/00

  Oxazine dyes · CPC title

• C09B69/008

  Dyes containing a substituent, which contains a silicium atom · CPC title

• C07D493/10

  Spiro-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title