Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols.

ABSTRACT: A series of gibberellic acid-based aminodiols was designed and synthesized from commercially available gibberellic acid. Exposure of gibberellic acid to hydrochloric acid under reflux conditions resulted in aromatization followed by rearrangement to form allo-gibberic acid. The key intermediate, ethyl allo-gibberate, was prepared according to literature methods. Epoxidation of key intermediate and subsequent ring-opening of the corresponding epoxide with different nucleophiles resulted in N-substituted aminodiols. The regioselective ring closure of N-benzyl-substituted aminodiol with formaldehyde was also investigated. All aminodiol derivatives were well characterized using modern spectroscopic techniques and evaluated for their antiproliferative activity against a panel of h

SUBMITTER: Khdar ZA 

PROVIDER: S-EPMC9499365 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature