Aminodiols, aminotetraols and 1,2,3-triazoles based on -gibberic acid: stereoselective syntheses and antiproliferative activities.

A new series of aminodiols, aminotetraols and 1,2,3-triazoles based on -gibberic acid were synthesized in a stereoselective manner, starting from commercially available gibberellic acid. -Gibberic acid, prepared from gibberellic acid according to a literature method, was applied to SeO/-BuOOH-mediated allylic oxidation, yielding the triol, which is a key intermediate. After protecting the 1,4-diol functionality as acetonide, epoxidation was performed using either -CPBA or -BuOOH/VO(acac) to produce the epoxy alcohol.

Gibberellic Acid (GA): A Versatile Chiral Building Block for Syntheses of Pharmaceutical Agents.

Gibberellic acid (GA), an ent-kaurene tetracyclic diterpene, has been considered to be a chiral pool for the chemical transformation of significant heterocyclic compounds. This chiral pool continues to influence modern synthetic chemistry as an inexpensive and versatile starting material since it is widely applied in agriculture. This review focuses on the stereoselective syntheses of bioactive agents with pharmaceutical potency prepared from Gibberellic acid.

Stereoselective synthesis and antiproliferative activity of -gibberic acid-based 1,3-aminoalcohol regioisomers.

A new library of -gibberic acid-based aminoalcohol regioisomers was synthesised stereoselectively starting from commercially available gibberellic acid, which yields -gibberic acid under mild acidic conditions. The successful formation of hydroxymethyl ketone derivative 5, by acid-mediated rearrangement of previously prepared epoxide, paved the way to obtain the desired 1,3-aminoalcohols through Schiff base formation. To obtain the desired regioisomers, the primary alcohol functionality of 5 was subjected to mesylation, then replaced with either primary amine or sodium azide.

Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols.

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.

New 1,3,4-thiadiazoles derivatives: synthesis, antiproliferative activity, molecular docking and molecular dynamics.

A series of 1,3,4-thiadiazole himachalene hybrids were prepared from the treatment of a himachalen-4-one thiosemicarbazone derivative with N-aryl-C-ethoxycarbonyl-nitrilimines and diarylnitrilimines via a 1,3-dipolar cycloaddition reaction. The structures were confirmed by NMR, IR and high-resolution mass spectroscopy (HRMS). The newly synthesized hybrid compounds were tested for their antitumor activities against a panel of cancer cell lines including fibrosarcoma (HT-1080), lung carcinoma (A-549) and breast carcinoma (MCF-7 and MDA-MB-231).

Design, synthesis, evaluation of new 3-acetylisoxazolines and their hybrid analogous as anticancer agents: In vitro and in silico analysis.

3-Acetylisoxazolines were synthesized by the reaction of natural (R)-limonene and (R)-carvone with acetone in the presence of iron (III) nitrate. The reaction showed to be highly peri- and regioselective. Next, using a 1,3-dipolar cycloaddition reaction, the mono-3-acylisoxazolines derived from these monoterpenes were evaluated for their reactivity with nitrilimines.