Huang, David S.; Wong, Henry L.; Georg, Gunda I. published the artcile< Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin>, Product Details of C10H11NS2, the main research area is pironetin analog preparation antitumor structure activity; antitumor agents; natural products; tubulin binding agents; α,β-unsaturated lactones; α-tubulin.
Pironetin is a natural product with potent antiproliferative activity that forms a covalent adduct with α-tubulin via conjugate addition into the natural product’s α,β-unsaturated lactone. Although pironetin’s α,β-unsaturated lactone is involved in its binding to tubulin, the structure-activity relationship at different positions of the lactone have not been thoroughly evaluated. For a systematic evaluation of the structure-activity relationships at the C4 and C5 positions of the α,β-unsaturated lactone of pironetin, twelve analogs of the natural product, I (R1 = R2 = H, Me; R1 = Me, n-Pr, CH2CF3, cyclopropyl, iso-Bu, CH2Ph, iso-Pr, R2 = H; R1 = H, R1 = Et) and II (R1 = Et, R2 = H; R1 = H, R2 = Et), were prepared by total synthesis. Modifying the stereochem. at the C4 and/or C5 positions of the α,β-unsaturated lactone of pironetin resulted in loss of antiproliferative activity in OVCAR5 ovarian cancer cells. While changing the C4 Et substituent with groups such as Me, Pr, cyclopropyl, and iso-Bu were tolerated, groups with larger steric properties such as an iso-Pr and benzyl groups were not.
ChemMedChem published new progress about Antitumor agents. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Product Details of C10H11NS2.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica