Isothiazoles. Part XV. A mild and efficient synthesis of new antiproliferative 5-sulfanylsubstituted 3-alkylaminoisothiazole 1,1-dioxides
Copyright policy )Isothiazoles. Part XV. A mild and efficient synthesis of new antiproliferative 5-sulfanylsubstituted 3-alkylaminoisothiazole 1,1-dioxides
5-Sulfanyl-3-alkylaminoisothiazole dioxide derivatives have been identified as a new class of potent inhibitors of rat aortic myocite proliferation. They were prepared by applying a simple methodology able to introduce a heteroatom on C-5 of the 3-alkylaminoisothiazole dioxide system. 3-Aminosubstituted-5-chloroisothiazole dioxides react smoothly not only with S-nucleophiles but also with N- and O-nucleophiles affording the corresponding 5-heterosubstituted isothiazole dioxides through an addition-elimination reaction. The behavior of 3-alkylamino-4-bromo-isothiazole 1,1-dioxide with S-, N- and O-nucleophiles affording the same products has also been described. On the contrary, the 3-amino-4,5-unsubstituted isothiazole dioxide system reacts easily only with sulfur nucleophiles affording the corresponding 4,5-dihydro-5-sulfanylderivatives through a simple Michael addition reaction.
- University of Padua Italy
- University of Milan Italy
- University of Washington United States
Male, Alkyl and Aryl Transferases, Alkylation, Molecular Structure, Myocytes, Smooth Muscle, Rats, Oxygen, Rats, Sprague-Dawley, Structure-Activity Relationship, Thiazoles, Cell proliferation (prepn. of 5-sulfanyl-substituted 3-alkylaminoisothiazole 1; 1-dioxides as inhibitors of cell proliferation and as inhibitors of PFTase and PGGTase-I), Animals, Enzyme Inhibitors, Farnesyl transferase; Isothiazoles; Nucleophilic addition; Smooth muscle cell, Cells, Cultured, Sulfur, Amination, Cell Proliferation
Male, Alkyl and Aryl Transferases, Alkylation, Molecular Structure, Myocytes, Smooth Muscle, Rats, Oxygen, Rats, Sprague-Dawley, Structure-Activity Relationship, Thiazoles, Cell proliferation (prepn. of 5-sulfanyl-substituted 3-alkylaminoisothiazole 1; 1-dioxides as inhibitors of cell proliferation and as inhibitors of PFTase and PGGTase-I), Animals, Enzyme Inhibitors, Farnesyl transferase; Isothiazoles; Nucleophilic addition; Smooth muscle cell, Cells, Cultured, Sulfur, Amination, Cell Proliferation
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