Journal of Medicinal Chemistry p. 752 - 757 (1991)
Update date:2022-08-03
Topics:
Randad, Ramnarayan S.
Mahran, Mona A.
Mehanna, Ahmed S.
Abraham, Donald J.
Three isomeric series of 2-(aryloxy)-2-methylpropionic acids were prepared and studied for their ability to decrease the oxygen affinity of human hemoglobin A.The isomeric aryloxy groups included 4-<<(aryloyl)amino>methyl>phenoxy, 4-(arylacetamido)phenoxy, and 4-<<(arylamino)carbonyl>methyl>phenoxy.A total of 20 compounds were synthesized and tested.Structure-activity relationships are presented.Several of the new compounds were found to be strong allosteric effectors of hemoglobin.The two most active compounds are 2-<4-<<(3,5-dichloroanilino)carbonyl>methyl>phenoxy>-2-methylpropionic acid and the corresponding 3,5-dimethyl derivative.The latter two compounds have been compared to other known potent allosteric effectors in the same assay and show greater activity.Both compounds also exhibit a right shift in the oxygen equilibrium curve when incubated with whole blood.The new compounds may be of interest in clinical or biological areas that require or would benefit from a reversal of depleted oxygen supply (i.e., ischemia, stroke, tumor radiotherapy, blood storage, blood substitutes, etc.).They are also structurally related to several marketed antilipidemic agents.
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