A series of dicarbonyl compds. have been designed and prepd. to mimic the rigid tetracyclic core of estradiol and dihydrotestosterone. Non-sym. tri- and tetra-substituted oxamides, e.g., I, were prepd. by the sequential addn. of primary and secondary amines to Ph cholorooxoacetate. Oxoamides, e.g., II, were prepd. via a Friedel-Crafts acylation/amide coupling protocol. Crystallog. data showed a good correlation between the structure of the dicarbonyl mimic and dihydrotestosterone complexed with the androgen receptor suggesting the mol. scaffolds may well prove versatile platforms for ligand design.
- tetra-substituted oxamides
- Ph cholorooxoacetate
Jones, I. L., Schofield, D. J., Strevens, R. R., Horton, P. N., Hursthouse, M. B., & Tomkinson, N. C. O. (2007). Novel steroid mimics: synthesis of tri- and tetra-substituted oxamides and oxoamides. Tetrahedron Letters, 48(4), 521-525. https://doi.org/10.1016/j.tetlet.2006.11.139