Fluorogenic 2-oxy-3(2H)-furanone materials

• US 3,969,373 A
• Filed: 06/26/1975
• Issued: 07/13/1976
• Est. Priority Date: 03/05/1973
• Status: Expired due to Term

• Current Assignee: Hoffmann-La Roche Incorporated (Roche Holding AG)
• Original Assignee: Hoffmann-La Roche Incorporated (Roche Holding AG)
• Inventors: Weigele, Manfred, Leimgruber, Willy, Grunberg, Emanuel, Cleeland, Roy Jr.
• Primary Examiner(s): Moatz, Harry I.
• Application Number:
  US05/590,655
• Time in Patent Office: 383 Days
• Field of Search: 260/347.8, 260/347.4, 260/347.5, 260/326.16, 260/347.3
• US Class Current: 549/477
• CPC Class Codes: C07C 45/58 in three-membered rings
• CPC Class Codes: C07C 49/215 polycyclic
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: C12Q 1/12 Nitrate to nitrite reducing bacteria
• CPC Class Codes: G01N 33/533 with fluorescent label
• CPC Class Codes: Y10S 436/80 Fluorescent dyes, e.g. rhodamine

Abstract

Compounds of the formula ##SPC1##

Wherein R₁ is lower alkyl or phenyl lower alkyl; R₂ is phenyl or substituted phenyl; and R₃ is substituted or unsubstituted phenyl, naphthyl or indolyl;

Are fluorogenic reagents which react with primary amino groups to form fluorophors. The above compounds are useful for fluorescent labeling of materials of biological importance.

Claims

1. A compound of the formula ##SPC4##

wherein R₁ is lower alkyl or phenyl lower-alkyl, R₂ is phenyl, lower-alkoxyphenyl, di-lower-alkoxyphenyl, carboxyphenyl or carboxy-lower-alkylphenyl and R₃ is phenyl or nitrophenyl.

2. A compound according to claim 1 wherein R₁ is lower alkyl.

3. A compound according to claim 1 wherein R₂ and R₃ are both phenyl.

4. The compound of claim 3 which is 2-methoxy-2,4-diphenyl-3(2H)-furanone.

5. The compound of claim 3 which is 2-ethoxy-2,4-diphenyl-3(2H)-furanone.

6. The compound of claim 3 which is 2-benzyloxy-2,4-diphenyl-3(2H)-furanone.

7. The compound of claim 2 which is 2-methoxy-2-phenyl-4(4-nitrophenyl)-3(2H)-furanone.

8. The compound of claim 2 which is 2-methoxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanone.

9. The compound of claim 2 which is 2-methoxy-2-phenyl-4-[4-(2-carboxyethyl)phenyl]-3(2H)-furanone.