3453-00-7Relevant articles and documents
Novel cobalt(0)- or magnesium-mediated approaches to β-ketophosphonates
Orsini, Fulvia,Di Teodoro, Emanuela,Ferrari, Marinella
, p. 1683 - 1688 (2002)
Two novel approaches to β-ketophosphonates, based on cobalt(0)- or magnesium-mediated reactions of α-halophosphonates with esters are described.
Synthesis and antiproliferative evaluation of new zampanolide mimics
Chen, Guanglin,Patanapongpibul, Manee,Jiang, Ziran,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,White, James D.,Chen, Qiao-Hong
, p. 3830 - 3844 (2019)
(?)-Zampanolide is a marine microtubule-stabilizing macrolide that has been shown by in vitro experiments to be a promising anticancer lead compound. Through its unique covalent-binding with β-tubulin, zampanolide exhibits cytotoxic potency towards multi-drug resistant cancer cells that is superior to paclitaxel. However, the limited availability of zampanolide impedes its further in vivo evaluation as a viable drug candidate. Zampanolide is envisioned to become more drug-like if its chemically fragile side chain can be stabilized; hence, this project aims to develop mimics of zampanolide with a stable side chain using straightforward synthetic methods. To this end, twelve novel zampanolide mimics (51-62) with conjugated and planar side chains have been synthesized via a 24-step sequence for each mimic from commercially available 2-butyn-1-ol as starting material. A Horner-Wadsworth-Emmons reaction incorporates the α,β-unsaturated ketone side chain and also closes the core macrocycle. WST-1 cell proliferation assays in three docetaxel-sensitive and two docetaxel-resistant human prostate cancer cell models confirm that a suitably designed side chain can serve as a bioisostere for the N-acyl hemiaminal side chain in zampanolide. Mimic 52 with a 17R chiral center was identified as the optimal candidate with IC50 values of 0.29-0.46 μM against both docetaxel-sensitive (PC-3 and DU145) and docetaxel-resistant prostate cancer cell lines (PC-3/DTX and DU145/DTX). Zampanolide mimic 52 exhibited equivalent antiproliferative potency towards both docetaxel-sensitive and docetaxel-resistant cell lines, with relative resistance in the range of 0.9-1.6.
Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessinggem-P-containing methanes
Touqeer, Saad,Ielo, Laura,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 2425 - 2429 (2021/04/02)
The direct transfer of different α-substituted methyllithium reagents to chlorinated phosphorous electrophiles of diverse oxidation state (phosphates, phosphine oxides and phosphines) is proposed as an effective strategy to synthesize geminal P-containing
Iron-Catalyzed and Air-Mediated C(sp3)?H Phosphorylation of 1,3-Dicarbonyl Compounds Involving C?C Bond Cleavage
Ou, Yingcong,Huang, Yuanting,Liu, Yu,Huo, Yanping,Gao, Yang,Li, Xianwei,Chen, Qian
supporting information, p. 5783 - 5787 (2020/11/30)
A C(sp3)?H phosphorylation has been achieved via the iron-catalyzed cross-coupling reactions between 1,3-dicarbonyl compounds and P(O)?H compounds involving C?C bond cleavages with air as the oxidant. This transformation provides a straightforward way to construct C(sp3)?P bonds, leading to the formation of β-ketophosphine oxides in up to 93% yield with good functional group tolerance. (Figure presented.).