Pyridylthio ketones

Abstract

Abstract PYRIDYLTHIO KETONES HAVING THE FOLLOWING STRUCTURAL FORMULA DISCLOSED. (1-(O=),R""-PYRID-2-YL)-SO2-(CH2)N-(C(-R)(-R''))M-CO- C6H3(-R")-R''" IN THE ABOVE R IS HYDROGEN, LOWER ALKYL OR PHENYL; R'' IS HYDROGEN, LOWER ALKYL OR PHENYL; R" AND R"" MAY BE HYDROGEN, ALKYL, HALO, ALKOXY, ALKYLTHIO, METHYLSULFONYL, METHYLSULFINYL, NITRO AMINO, PHENYL, OR TAKEN TOGETHER TO BE METHYLENEDIOXY OR BENZO; RIV MAY BE HYDROGEN, LOWER ALKYL, HALO, NITRO OR PHENYL. THE SULFUR ATOM MAY BE OXIDIZED TO SULFOXIDE, SULFONE OR NON-OXIDIZED AS THE SULFIDE. THE VALUES FOR M AND N MAY BE 0, 1, 2 OR 3. THESE COMPOUNDS ARE USEFUL AS ANTIFUNGAL AND ANTIBACTERIAL AGENTS. SOME OF THE COMPOUNDS ALSO EXHIBIT ANTISECRETORY AND IMMUNO SUPPRESSANT ACTIVITY. THE PYRIDYLTHIO COMPOUNDS ARE PREPARED BY THE REACTION OF A SALT OF A 2-MERCAPTO PYRIDINE-N OXIDE (II) (M=CATIONIC SPECIES) WITH A SUITABLY SUBSTITUTED COMPOUND III (WHERE X=CHLORO OR BROMO) IN AN (1-(O=),R""-PYRID-2-YL)-S-M(+), AND R"-C6H3(-R''")-CO- (C(-R)(-R''))M-(CH2)N-X -> (1-(O=),R""-PYRID-2-YL)-S- (CH2)N-(C(-R)(-R''))M-CO-C6H3(-R")-R''" APPROPRIATE SOLVENT (SUCH AS WATER, ALCOHOLS, DMSO, DMF, ACETONITRILE, ETC.). THESE REACTIONS ARE USUALLY CARRIED OUT ABOVE ROOM TEMPERATURE AND WHEN COMPLETE, THE PRODUCT IS PRECIPITATED (IF NECESSARY) BY ADDITION OF WATER AND COOLING. OXIDATION OF THE PYRIDYLTHIO COMPOUNS OF TYPE IV WITH PERACIDS SUCH AS M-CHLOROPERBENZOIC, PERFORMIC OR PERACETIC GIVE THE PYRIDYLSULFINYL COMPOUNDS OF TYPE V. (1-(O=),R""-PYRID-2-YL)-SO-(CH2)N-(C(-R)(-R''))M-CO- C6H3(-R")-R''" OXIDATION OF COMPOUNDS OF TYPE IV WITH AT LEAST TWO MOLES OF OXIDIZING AGENT RESULTS IN THE PREPARATIO OF KETO SULFONES OF TYPE VI. THE SAME COMPOUNDS ARE PREPARED BY THE OXIDATION OF SULFOXIDES OF TYPE V. (1-(O=),R""-PYRID-2-YL)-SO2-(CH2)N-(C(-R)(-R''))M-CO- C6H3(-R")-R''" THESE COMPOUNDS ARE USEFUL AS ANTI-FUNGAL AND ANTIBACTERIAL AGENTS. SOME OF THE COMPOUNDS ALSO EXHIBIT ANTI-SECRETORY AND IMMUNOSUPPRESSANT ACTIVITY.

Inventors

• 👤 D Kaminsky
• 👤 M Wise

Bibliographic Details