Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidaseElectronic supplementary information (ESI) available: Proton NMR spectra for the intermediate piperidines 56–60 and acetylenes 63-81 and 85,86. See http://www.rsc.org/suppdata/ob/b2/b209165h/

Abstract

The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.

Alkynylgold(I) C3‐Chiral Concave Complexes: Aggregation and Luminescence

“…CTB(H,C 2 H) was obtained in two steps in 80 % overall yield from CTB(H,OTf) [56] by Sonogashira cross‐coupling with trimethysilylacetylene using [Pd(PPh 3 ) 2 Cl 2 ] as catalyst and Et 3 N as base, followed by removal of the TMS protecting groups with tetrabutylammonium fluoride [66] . The trinuclear gold complexes CTB(H,C 2 AuPR 3 ) (R=Ph: 1 ; R=Et: 2 , and R=Cy: 3 ), were prepared by nucleophilic substitution of [Au(PR 3 )Cl] (R=Ph, Et, and Cy) in the presence of sodium methoxide [67,68] .…”

An Adamantyl-Substituted Retinoid-Derived Molecule That Inhibits Cancer Cell Growth and Angiogenesis by Inducing Apoptosis and Binds to Small Heterodimer Partner Nuclear Receptor: Effects of Modifying Its Carboxylate Group on Apoptosis, Proliferation, and Protein-Tyrosine Phosphatase Activity

“…The nitro group in the coupled product, 51 , was then transformed to the bromo group by reduction to the amine and diazotization under hydrophobic conditions using tert -butyl nitrite in the presence of cupric bromide . Aryl bromide 53 underwent Sonagashira coupling with trimethylsilylacetylene to give the protected phenylacetylene 54 . Desilylation of 54 with tetra( n -butyl)ammonium fluoride 52 provided phenylacetylene 55 .…”

Total Synthesis of Gastrodinol via Photocatalytic 6π Electrocyclization

“…Then we came to the final stage of the synthesis of key segment 4 : Sonogashira coupling between sulfonic ester 13 and (triisopropylsilyl)­acetylene. Initially, we applied the reaction conditions reported in the literature which yielded desired product 14 with a conversion rate of less than 50% . After a few attempts, we found that a phase transfer catalyst (TBAB) could shorten the reaction time obviously and achieve complete conversion .…”

“…Initially, we applied the reaction conditions reported in the literature which yielded desired product 14 with a conversion rate of less than 50%. 14 After a few attempts, we found that a phase transfer catalyst (TBAB) could shorten the reaction time obviously and achieve complete conversion. 15 Finally, deprotection of silyl ether 14 proceeded smoothly to afford key segment phenylacetylene 4.…”