Mh220250.rar
Mh220250.rar
A structure-activity relationship (SAR) study of a series of 9-oxo-N-substituted pyran-4-amines was performed in an effort to further delineate this class of RAR-agonist. While a number of compounds were capable of inducing skeletal myogenesis in immature myoblasts, no compounds were identified with a greatly enhanced (RAR)-selectivity. The most potent agonist 6 was capable of inducing some in vivo differentiation of rhabdomyosarcoma cells in tumor-bearing rats, however this was accompanied by evidence of toxicity and was not enhanced by the presence of an RXR-selective retinoid 9. In addition, pyran-4-amine 6 was not an agonist for retinoic acid receptor β (RAR-β), a finding that distinguished the high affinity agonist, AGN-193836 (1) from this class of RAR-selective retinoid. A side-chain modification was conducted on the pyran-4-amine class, and based on data from our initial SAR, illustrated here, did not generate compounds with a greatly improved selectivity. Examination of the effect of the introduction of a methyl group on the oxygen atom (6b) and removal of the oxime function (6c) illustrated the impact that these changes were having on the RAR-selectivity and affinity of the molecule. The SAR demonstrated that the greatest loss of affinity for the RAR was observed with the removal of the oxime function, where compound 6c showed a three-fold loss in potency. Subsequent introduction of a methyl group (6e) caused a decrease in activity for both RAR and RXR. The introduction of a different oxygen atom (O-methyl) and a different oxime moiety (methyl) produced a much reduced impact on RAR-selectivity for both compounds (6e and 6h), when compared to the native compound 6a. For the RAR-RXR pair, the introduction of either a methyl or methoxy group (6j) on the oxygen atom reduced potency as expected, however, the lack of RAR-selectivity with a methoxy group, illustrated by compound 6k, was unexpected for this class of compounds. The most interesting result of this SAR study was the loss in affinity that was observed with the removal of the oxime group. We conclude that this class of RAR-agonist warrants further development, particularly in the area of improving RAR-selectivity.
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