56691-74-8Relevant articles and documents
Enantioselective Synthesis Muqubilin and Negombatoperoxides B and C/D
Wang, Xiao-Tao,Wu, Yikang
, p. 4205 - 4219 (2021/03/01)
Muqubilin, negombatoperoxide B, and negombatoperoxide C/D were synthesized through enantioselective routes, with the quaternary center derived from a peroxy chiral building block of known absolute configuration. The C-2/C-3 stereogenic centers were introduced by asymmetric aldol condensation, and the 1,2-dioxane ring was constructed via an intramolecular alkylation of a hydroperoxide with a mesylate. The synthetic samples showed physical and spectroscopic data consistent with those reported in the literature and thus verified the configurations of the natural products. A potentially more expeditious enantioselective entry to the 1,2-dioxane-aldol moiety (C-1 to C-6) of such cyclic peroxides was also briefly explored, where the C-2/C-3 stereogenic centers were installed through a [2+2] cycloaddition and the 1,2-dioxane ring was closed via an intramolecular alkylation coupled with an alkyl-oxygen cleavage of a β-lactone.
Synthesis, antimicrobial and antineoplastic activities for agelasine and agelasimine analogs with a β-cyclocitral derived substituent
Proszenyak, Agnes,Charnock, Colin,Hedner, Erik,Larsson, Rolf,Bohlin, Lars,Gundersen, Lise-Lotte
, p. 625 - 634 (2008/12/21)
Agelasines and agelasimines are antimicrobial and cytotoxic purine derivatives isolated from marine sponges (Agelas sp.). We have synthesized structurally simplified analogs of these natural products starting from β-cyclocitral. The novel compounds were found to be strong inhibitors of a wide variety of pathogenic microorganisms (incl. Mycobacterium tuberculosis) as well as cancer cell lines. The biological activities were generally in the same range as those previously found for the structurally more complex agelasines and agelasimines isolated in small amounts from natural sources. We also report for the first time that agelasine and agelasimine analogs inhibit growth of protozoa (Acanthamoeba castellanii and Acanthamoeba polyphaga). Acanthamoeba keratitis is an increasingly common and severe corneal infection, closely associated with contact lens wear.
3-(15-hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one and its effect on neuropeptide secretion
Girlanda-Junges, Celine,Lutz-Bucher, Bernadette,Gonzalez de Aguilar, Jose-Luis,Loeffler, Jean-Philippe,Luu, Bang
, p. 2537 - 2539 (2007/10/03)
The aim of the present study was to describe the synthesis of a trimethyl cyclohexenonic long chain fatty alcohol (t-CFA), and analyze its biological activity. Specifically, 3-(15-hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one, the t-CFA containing