Selenophene-fused aromatic compound and manufacturing method thereof

Patent metadata

Field	Value
Publication number	US-9365590-B2
Application number	US-201414228493-A
Country	US
Kind code	B2
Filing date	Mar 28, 2014
Priority date	Sep 28, 2011
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

The present disclosure relates to a method for more easily and economically producing a selenophene-fused aromatic compound derivative containing various substituents and the selenophene-fused aromatic compound produced according to the method, and the selenophene-fused aromatic compound can be used for various purposes such as an intermediate of an anti-bacterial or anticancer substance, an indicator of which color is changed depending on a solvent, or a fluorescent substance.

First claim

We claim:

1. A selenophene-fused aromatic compound comprising:
a compound represented by the following Chemical Formula 1:

wherein R 1 is selected from the group consisting of —CO 2 H, —CO 2 R, 4-NO 2 -Ph, 4-CN-Ph, 4-RO 2 C-Ph, 4-X-Ph, or the following Chemical Formula A:

R 2 is selected from the group consisting of —NHCOR, —CX 3 , —OR, -diOR, —OH, a substitutable alkylene-dioxy group, a substitutable amino group, or a halo group;
X represents a halo group,
R 3 is selected from the group consisting of —OH, or —NH 2 ,
R 4 and R 5 are C;
R 6 represents H, or a substitutable alkoxy group,
R 7 represents H,
R 8 represents a halo group, and
R is selected from the group consisting of H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative.

2. The selenophene-fused aromatic compound of claim 1 , wherein Chemical Formula 1 is selected from the following Chemical Formula:

wherein in the formula,
R 11 represents —CO 2 H, —CO 2 R, 4-NO 2 -Ph, 4-CN-Ph, 4-RO 2 C-Ph, or 4-X-Ph,
R 12 represents —NHCOR, —CX 3 , —OR, -diOR, —OH, a substitutable alkylene-dioxy group, a substitutable amino group, or a halo group,
X represents a halo group, and
R represents H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative.

3. A selenophene-fused aromatic compound comprising:
a compound represented by the following Chemical Formula 1:

wherein R 1 is selected from the group consisting of —CO 2 R a , 4-NO 2 -Ph, 4-CN-Ph, 4-RO 2 C-Ph, 4-X-Ph, or the following Chemical Formula A:

R 2 is selected from the group consisting of —NHCOR, —CX 3 , —OR, -diOR, —OH, a substitutable alkylene-dioxy group, a substitutable amino group, or a halo group;
X represents a halo group,
R 3 is selected from the group consisting of H, —OH, or —NH 2 ,
R 4 and R 5 are C;
R 6 represents H, or a substitutable alkoxy group,
R 7 represents H,
R 8 represents a halo group,
R a is selected from the group consisting of H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative; and,
R is selected from the group consisting of H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative.

4. The selenophene-fused aromatic compound of claim 3 , wherein Chemical Formula 1 is selected from Chemical Formulas 7 and 8:

wherein in the formulas,
R 4 and R 5 are C;
R 11 is selected from the group consisting of —CO 2 R a , 4-NO 2 -Ph, 4-CN-Ph, 4-RO 2 C-Ph, or 4-X-Ph,
R 12 is selected from the group consisting of —NHCOR, —CX 3 , —OR, -diOR, —OH, a substitutable alkylene-dioxy group, a substitutable amino group, or a halo group,
X represents a halo group,
R a is selected from the group consisting of H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative, and,
R represents H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative.

5. The selenophene-fused aromatic compound of claim 3 , wherein Chemical Formula 1 is selected from Chemical Formulas 10 to 12:

wherein in the formulas,
R 2 is selected from the group consisting of —NHCOR, —CX 3 , —OR, -diOR, —OH, a substitutable alkylene-dioxy group, a substitutable amino group, or a halo group,
R 4 and R 5 are C;
R 6 represents H, or a substitutable alkoxy group,
R 7 represents H,
R 8 represents a halo group,
L represents a linker, and
R represents H, a substitutable alkyl group, a substitutable aryl group, a substitutable amino group, a substitutable amino acid group, a substitutable peptide group, a substitutable C 1-7 alkoxy group, or a residue of a substitutable carbohydrate or carbohydrate derivative.

6. An anti-bacterial composition, an indicator composition, a fluorescent composition or an anticancer composition comprising a selenophene-fused aromatic compound according to claim 1 .

7. A method of producing the selenophene-fused aromatic compound represented by Chemical Formula 4 of claim 2 , the method comprising:
preparing a reaction mixture containing a diselenide compound represented by a general formula of R 11 —CH 2 —Se—Se—CH 2 —R 11 , a solvent, and a reducing agent; and
adding an aromatic starting material represented by Chemical Formula 4a and a base to the reaction mixture to be reacted:

8. A method of producing the selenophene-fused aromatic compound represented by Chemical Formula 6 of claim 2 , the method comprising:
preparing a reaction mixture containing a diselenide compound represented by a general formula of R 11 —CH 2 —Se—Se—CH 2 —R 11 , a solvent, and a reducing agent; and
adding an aromatic starting material represented by Chemical Formula 6a and a base to the reaction mixture to be reacted:

9. The method of claim 7 , wherein the reducing agent contains a thiol group.

10. A producing method of producing the selenophene-fused aromatic compound represented by Chemical Formula 7 according to claim 4 , the method comprising:
reacting an aromatic starting material represented by Chemical Formula 7a and R 11 CH 2 X via heating to form a reaction intermediate represented by Chemical Formula 7b; and
adding a solvent and a base to the reaction intermediate to be reacted:

wherein
R 13 represents a substitutable alkyl group.

11. A method of producing the selenophene-fu

Assignees

• Univ Sejong Ind Acad Coop Gr
• Samsung Life Public Welfare Foundation

Inventors

• Lim Dongyeol
• Nam Do-Hyun
• Dubey Rashmi
• Lee Hangeun

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• C07D421/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D517/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D345/00 Primary

  Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms · CPC title