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.
“…(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.…”
Section: Literature Citedmentioning
confidence: 99%
“…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.…”
because the ortho aromatic protons of some compounds are found several cps (15-40) upfield with respect to the other (meta and para) protons.In fact, when the shielded ortho protons belong to 1,2disubstituted central ring-i.e., Table V: compounds 3-5the four central nuclear protons show the characteristic
“…(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.…”
Section: Literature Citedmentioning
confidence: 99%
“…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.…”
because the ortho aromatic protons of some compounds are found several cps (15-40) upfield with respect to the other (meta and para) protons.In fact, when the shielded ortho protons belong to 1,2disubstituted central ring-i.e., Table V: compounds 3-5the four central nuclear protons show the characteristic
“…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.…”
“…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.…”
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