Thyromimetics. VII. Isopropyl Analogs of Thyroid Hormones

Abstract

Attempts were made to prepare thyroidal hormones with isopropyl groups in place of the iodine atoms. 3,3'-Diisopropyl-and 3,3',5'-triisopropyl-DL-thyronines (I and III) were prepared successfully. The more desirable isopropyl analogs of 3,3',5-triiodothyronine (l-Ts) and thyroxine (II and IV) were not obtained. A number of possible routes to II and IV were studied and are described. Ill was tested and found inactive as a hypocholesteremic or antigoitrogenic agent and as an inhibitor of L-Ts.

Synthesis of biphenyl portion of decinine

“…(6) Hauser, C. R., Hoffenberg, D. S., Puterbaugh, W. H., Frostick, F. C., ibid., 20, 1531 (1955). (7) Huston, R. C., Ewing, D. T., J. Amer. Chem.…”

“…The conversion of 8a and b to the cinnamic acids 6a and b, the reduction of 8a in aqueous potassium hydroxide to the propionic acid 9a, and the esterification of 9a to 9b proceeded readily, and in good yields. The chloromethylation of 9a and b with chloromethylmethyl ether (12) or paraformaldehyde and hydrogen chloride (7,29) gave poor yields of the solid chloromethyl derivatives 10a and b. Completion of the Sommelet reaction (2) did not lead to the isolation of any aldehyde.…”

Some compounds active as antirhinovirus in the plaque inhibition test

“…Previous attempts to synthesize 3,5-diisopropyl analogs of T3 failed. 6 In the present paper we report the synthesis of 3,5-diisopropvl-3'-iodo-DL-thyronine as summarized in Scheme I.…”

The synthesis of 3,5-diisopropyl-3'-iodo-DL-thyronine

“…Previous attempts to synthesize 3,5-diisopropyl analogs of T3 failed. 6 In the present paper we report the synthesis of 3,5-diisopropvl-3'-iodo-DL-thyronine as summarized in Scheme I.…”