237069-31-7Relevant articles and documents
Synthesis and evaluation of azole-substituted 2-aryl-6-methoxy-3,4- dihydronaphthalenes and -naphthalenes as inhibitors of 17α-hydroxylase- C17,20-Lyase (P450 17)
Zhuang, Yan,Hartmann, Rolf W.
, p. 25 - 30 (2007/10/03)
The synthesis and biological evaluation of azole-substituted 3,4- dihydronaphthalenes (7a, 7b, 14a, 14b) and naphthalenes (12a, 12b, 16a, 16b) as nonsteroidal inhibitors of 17α-hydroxylase-C17,20-lyase (P450 17, CYP 17) are described. In the case of the dihydronaphthalenes, introduction of the phenyl substituent into the 2-position was accomplished by coupling 2- hydroxy-3,4-dihydronaphthalene-2-trifluoromethanesulfonate 1 with the corresponding aryl-Zn-bromides 4a and 4b in the presence of Pd(PPh3)4 as catalyst yielding 5a and 5b as key intermediates. In the case of the naphthalenes, 2-bromonaphthalene 9 was reacted with the corresponding Grignard reagents yielding 10a and 10b. After transformation of the intermediate acetals 5a, 5b, 10a, 10b into the corresponding aldehydes, the latter compounds were reacted with tosylmethyl isocyanide and K2CO3 to give the oxazoles 7a, 7b, 12a, and 12b. The imidazoles 14a, 14b, 16a, and 16b were prepared by heating the corresponding 4-tosyloxazolines in ammonia, which were prepared by reacting the aldehydes with tosylmethyl isocyanide and NaCN. Using a microsomal fraction of human testicular enzyme, the title compounds did not inhibit the target enzyme.
