Solid-phase synthesis of libraries of ethynylated aminosteroid derivatives as potential antileukemic agents was written by Talbot, Amelie;Maltais, Rene;Kenmogne, Lucie Carolle;Roy, Jenny;Poirier, Donald. And the article was included in Steroids in 2016.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:
Steroids possessing an ethynyl group at position 17伪 (tertiary alcs.) are well known to be more stable than their non-ethynyl analogs (secondary alcs.). To facilitate the development of new drugs with better metabolic stability, we developed a new diethylsilyl acetylenic linker allowing us to rapidly synthesize libraries of ethynylated steroid derivatives using a solid-phase strategy. To illustrate its usefulness, this linker was used to expand the mol. diversity of a lead compound having a hydroxy acetylenic pattern and to potentially find new compounds with interesting cytotoxic activity against leukemia cell lines. Herein, we report the chem. synthesis and the characterization of three libraries of ethynylated aminosteroid derivatives using the diethylacetylenic linker. We discuss their antiproliferative activities obtained in 2 leukemia cell lines (HL-60 and Jurkat), which results provided new structure-activity relationships. We also identified a new promising aminosteroid derivative with an azetidine moiety, compound I, inhibiting 60% and 75% of HL-60 and Jurkat cell proliferation, resp., at 1 渭M. More generally, these results validate the use of a diethylsilyl acetylenic linker for researchers interested in generating libraries of alc. derivatives with better stability and drug profile. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).
(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N鈥揌 bond in an axial position, and the other in an equatorial position.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem