76132-43-9Relevant academic research and scientific papers
Selective α-Deuteration of Cinnamonitriles using D2O as Deuterium Source
Guo, Beibei,de Vries, Johannes G.,Otten, Edwin
supporting information, p. 179 - 186 (2021/10/12)
The selective α-deuteration of α,β-unsaturated nitriles using the strong base tBuOK or a metal-ligand cooperative Ru pincer catalyst is described. With D2O as deuterium source and glyme as solvent at 70 °C, tBuOK is an efficient catalyst for deuteration at the α-C(sp2) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the tBuOK-catalysed protocol does not tolerate base-sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein's ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal-ligand cooperative Ru catalyst is found to be significantly higher than that of tBuOK, allowing reactions to proceed well even at room temperature. A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α-CH position when using tBuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa-Michael addition of D2O. (Figure presented.).
Rhodium-Catalyzed Cyanation of C(sp2)-H Bond of Alkenes
Chaitanya, Manthena,Anbarasan, Pazhamalai
, p. 3766 - 3769 (2015/08/18)
Efficient and selective rhodium-catalyzed cyanation of chelation-assisted C-H bonds of alkenes has been accomplished using environmentally benign N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as a cyanating reagent. The developed methodology tolerates various functional groups and allows the synthesis of diverse substituted acrylonitriles in good to excellent yields. Furthermore, the potential of the methodology was demonstrated through the formal synthesis of chlorpheniramine-based antagonist.
Chlorpheniramine Analogues Reverse Chloroquine Resistance in Plasmodium falciparum by Inhibiting PfCRT
Deane, Karen J.,Summers, Robert L.,Lehane, Adele M.,Martin, Rowena E.,Barrow, Russell A.
supporting information, p. 576 - 581 (2014/06/09)
The emergence and spread of malaria parasites that are resistant to chloroquine (CQ) has been a disaster for world health. The antihistamine chlorpheniramine (CP) partially resensitizes CQ-resistant (CQR) parasites to CQ but possesses little intrinsic antiplasmodial activity. Mutations in the parasite's CQ resistance transporter (PfCRT) confer resistance to CQ by enabling the protein to transport the drug away from its site of action, and it is thought that resistance-reversers such as CP exert their effect by blocking this CQ transport activity. Here, a series of new structural analogues and homologues of CP have been synthesized. We show that these compounds (along with other in vitro CQ resistance-reversers) inhibit the transport of CQ via a resistance-conferring form of PfCRT expressed in Xenopus laevis oocytes. Furthermore, the level of PfCRT-inhibition was found to correlate well with both the restoration of CQ accumulation and the level of CQ resensitization in CQR parasites.
Copper-catalyzed asymmetric reduction of 3,3-diarylacrylonitriles
Lee, Daehyung,Yang, Youngmin,Yun, Jaesook
, p. 2749 - 2751 (2008/02/07)
Equation Presented CuH-catalyzed enantioselective conjugate reduction of 3,3-diaryl-substituted acrylonitriles is described. A range of 3-aryl-3-pyridylacryionitriles were reduced with high levels of enantioselectivity under optimal conditions employing a
