Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes

Abstract

Upper rim substituted tetraiodo calix [4]arenes are coupled to a variety of acrylamides using the palladium catalysed Heck reaction. Tetra-acrylamido upper rim substituted calix [4]arenes are obtained in good yields with exceptionally high stereoselectivity, to produce the all-trans isomers. Tetra-acrylamido calix[4]arenes derived from secondary acrylamides are shown to dimerise via eight hydrogen bonds to form dimeric capsules, which are able to include small organic molecules.

Design, synthesis and evaluation of novel polypharmacological antichlamydial agents

“…N-Acylation of 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide 3 with acryloyl chloride and NaH gave 12 in 47% yield and coupling of Boc-hydrazide to 4-bromobenzoic acid in presence of EDC$HCl and DMAP [23] yielded 4-bromobenzene-Boc- hydrazide 13 in 45% yield. The building blocks 12 and 13 were subjected to Heck coupling by using Pd(OAc) 2 as a catalyst and the ligand 1,3-bis(diphenylphosphino)propane (dppp) [24] to obtain intermediate 14a in 29% yield. Finally the Boc group was removed to achieve the hydrazide 14b as a HCl salt in 90% yield.…”

Hill coefficients of dietary polyphenolic enzyme inhibitiors: can beneficial health effects of dietary polyphenols be explained by allosteric enzyme denaturing?

“…With values of n>1, more than one molecule interacts with the receptor or enzyme. The value of n H corresponds to the reaction stoichiometry in supramolecular chemistry obtained through JOB plots [11]. Surprisingly for the large majority of dose-response curves analyzed by Prinz, a value of n>1 was observed.…”

Regioselective and Enantioselective Hydroformylation of Dialkylacrylamides

“…Dialkylacrylamides 1b, 1c and 1d were prepared according to literature procedures. [20,21] Me CgPPh and the POP ligands were prepared according to the literature. [3b,14] Other chiral ligands were donated by Chirotech.…”