Syntheses and spectral studies of some dienic and enynic esters

Multidrug resistance (MDR) reversers: High activity and efficacy in a series of asymmetrical N,N-bis(alkanol)amine aryl esters

“…The other designed compounds 1e2, 4e8 and 10e26 were eventually obtained by reaction of 54e68 with the proper carboxylic acid using EDCI and DMAP in anhydrous CH 2 Cl 2 . The suitable acids are either commercially available ((E)-3-(3,4,5-trimethoxyphenyl)acrylic acid, 3,4,5-trimethoxybenzoic acid, anthracene-9-carboxylic acid, 9H-fluorene-carboxylic acid), synthesized according to the literature (3-(3,4,5-trimethoxyphenyl)propiolic acid [34,35]) or synthesized as reported in Scheme 2. Commercially available quinine and quinidine were transformed in the corresponding ethyl acetate derivatives 69 and 70, which yielded the acids 71 and 72 after alkaline hydrolysis (Scheme 2).…”

Intramolecular Diels-Alder reactions. 10. Synthesis and cyclizations of some N-(cinnamyl and phenylpropargyl)cinnamamides and phenylpropiolamides

“…Phenylpropargylamine Hydrochloride (2). N-(Phenylpropargyl)phthalimide was prepared from phenylpropargyl chloride10 and K phthalimide in a manner similar to that previously described,27 mp 152.…”

“…Cyclization of a seventh parent amide will be considered in a subsequent paper. 8 Used in the syntheses of the unsaturated amides were the hydrochloride salts of trans -cinnamylamine (l),9 phenylpropargylamine (2), and cis -cinnamylamine (3). Amine salt 2 was obtained in 79% overall yield by Gabriel synthesis from phenylpropargyl chloride.10 Low-pressure catalytic hydro-genation of 2 in the presence of Pd-BaSOi-quinoline gave nearly a quantitative yield of 3.…”

Arylamino Esters As P‐Glycoprotein Modulators: SAR Studies to Establish Requirements for Potency and Selectivity

“…The reaction between 13 and the commercially available amino alcohol 3‐aminopropan‐1‐ol led to 14 , which was alkylated by reductive methylation with HCOOH/HCHO to give the tertiary amine 15 . The final compound 5 was obtained by esterification of 15 with 3‐(3,4,5‐trimethoxyphenyl)propiolic acid,20 using the same procedure described above.…”

“… Reagents and conditions : a) Br(CH 2 ) 3 OH, EDCI, DMAP, anhydrous CH 2 Cl 2 , RT, 48 h, 96 %; b) NH 2 (CH 2 ) 3 OH, anhydrous CH 3 CN, 60 °C, 6 h, 36 %; c) HCOOH/HCHO, EtOH, 80 °C, 5 h, 78 %; d) 3‐(3,4,5‐trimethoxyphenyl)propiolic acid,20 EDCI, DMAP, anhydrous CH 2 Cl 2 , RT, 72 h, 10 %. …”