Antitumour benzothiazoles. Part 15: The synthesis and physico-chemical properties of 2-(4-aminophenyl)benzothiazole sulfamate salt derivatives.
A series of sulfamate salt derivatives of the potent and selective 2-(4-aminophenyl)benzothiazole antitumour agents has been prepared and their evaluation as potential prodrugs for parenteral administration carried out. The salts were sparingly soluble under aqueous conditions (pH 4-9), and degradation to the active free amine was shown to occur under strongly acidic conditions. The salts were found to be markedly less active than their parent amines against sensitive human tumour cell lines in vitro.
Shi
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Cancer Research Laboratories, School of Pharmaceutical Sciences, University of Nottingham, UK.
Bradshaw
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Chua
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Westwell
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Stevens
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D000588:Amines / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles; D001943:Breast Neoplasms / Q000188:drug therapy; D004355:Drug Stability; D020536:Enzyme Activators / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006162:Guanylate Cyclase / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D006863:Hydrogen-Ion Concentration; D020128:Inhibitory Concentration 50; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011355:Prodrugs / Q000737:chemistry* / Q000494:pharmacology; D012995:Solubility; D013451:Sulfonic Acids / Q000138:chemical synthesis*; D013844:Thiazoles / Q000737:chemistry* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
C111133:2-(4-aminophenyl)benzothiazole; D000588:Amines; D000970:Antineoplastic Agents; D052160:Benzothiazoles; D020536:Enzyme Activators; D010975:Platelet Aggregation Inhibitors; D011355:Prodrugs; D013451:Sulfonic Acids; D013844:Thiazoles; C005741:sulfamic acid; D006162:Guanylate Cyclase; C005465:benzothiazole