Synthesis of a novel dual inhibitor of thromboxane A2 synthetase and 5-lipoxygenase (E3040) via the direct coupling reaction of hydroquinone with 3-pyridinecarboxaldehyde.
Synthesis of a novel dual inhibitor of thromboxane A2 synthetase and 5-lipoxygenase, 5,7-dimethyl-6-hydroxy-2-methylamino-4-(3- pyridylmethyl)benzothiazole (E3040), was accomplished via a new coupling reaction, in which a key intermediate, (3,6-dihydroxy-2,4-dimethylphenyl)-(3-pyridyl)methanol, was easily synthesized in a high yield from 2,6-dimethyl-1,4-benzohydroquinone and 3-pyridinecarboxaldehyde in 6 N hydrochloric acid. The regio isomers of 3-pyridinecarboxaldehyde also gave the corresponding coupling products in high yields.
Komatsu
Y
Y
Eisai Tsukuba Research Laboratories, Ibaraki, Japan.
Minami
N
N
D052160:Benzothiazoles; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013930:Thromboxane-A Synthase / Q000037:antagonists & inhibitors*
D052160:Benzothiazoles; D016859:Lipoxygenase Inhibitors; D011725:Pyridines; D013844:Thiazoles; C095803:E 3040; D013930:Thromboxane-A Synthase