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Novel steroid mimics: synthesis of tri- and tetra-substituted oxamides and oxoamides

Jones, Ian L. and Schofield, Daniel J. and Strevens, Robert R. and Horton, Peter N. and Hursthouse, Michael B. and Tomkinson, Nicholas C. O. (2007) Novel steroid mimics: synthesis of tri- and tetra-substituted oxamides and oxoamides. Tetrahedron Letters, 48 (4). pp. 521-525. ISSN 0040-4039

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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.