Synthesis of novel isoxazole-linked steroidal glycoconjugates—an application of a novel steroidal nitrile oxide

C‐3β‐Tethered Functional Cholesterol Conjugates by Nitrile Oxide Alkyne Cycloaddition (NOAC)

“…Steroidal glycoconjugate formation is demonstrated by the regioselective formation of 23 (85 %) by the reaction of putative nitrile oxide p-17 with protected d-galactose 22 as a model sugar dipolarophile. [17] The selective tethering of one or two cholesterol units to a thymidine skeleton was demonstrated by trapping of the same dipole by 5Ј-protected mono-or bis-propargylated thymidines 24 or 26 [18] to give conjugates 25 and 27 in 81 and 68 % yields, respectively (Scheme 5). The mono-and bis-steroidal conjugates are potentially useful building blocks for the formation of syn-thetic oligonucleotides with tuneable amphiphilic properties.…”

Pillar[5]arene-Based Polycationic Glyco[2]rotaxanes Designed as Pseudomonas aeruginosa Antibiofilm Agents

“…1 LecB were produced in Escherichia coli, purified by affinity chromatography, dialyzed, and lyophilized as previously described. 29 Protein concentration was assessed using Nanodrop 2000 UV−vis spectrophotometer by measurement of absorbance at 280 nm using a theoretical molarity extinction coefficient of 27 960 and 6990 nM −1 cm −1 for LecA and LecB, respectively. ITC experiments were performed with a VP-ITC isothermal titration calorimeter (Micro-Cal-Malvern).…”

Steroids: partial synthesis in medicinal chemistry

“…Methods for the addition of extra carbocyclic and heterocyclic rings at C-16 and their influence on the biological activity of the pregnanes have been reported. [148][149][150] The role of glucocorticoids in the treatment of asthma has been reviewed, 151 whilst the use of inhibitors of the 11b-hydroxy steroid dehydrogenase in glucocorticoid metabolism as a treatment for type 2 diabetes has been described. 152 Novel adenylyl cyclase inhibitors based on C-21 phenylsulfonates (e.g.…”