74447-44-2Relevant academic research and scientific papers
Synthesis and evaluation of (2-phenethyl-2H-1,2,3-triazol-4-yl)(phenyl)methanones as Kv1.5 channel blockers for the treatment of atrial fibrillation
Blass, Benjamin E.,Coburn, Keith,Lee, Wenlin,Fairweather, Neil,Fluxe, Andrew,Wu, Shengde,Janusz, John M.,Murawsky, Michael,Fadayel, Gina M.,Fang, Bin,Hare, Michelle,Ridgeway, Jim,White, Ron,Jackson, Chris,Djandjighian, Laurent,Hedges, Richard,Wireko, Fred C.,Ritter, Amanda L.
, p. 4629 - 4632 (2006)
A series of novel (2-phenethyl-2H-1,2,3-triazol-4-yl)(phenyl)methanones were prepared and examined for utility as Kv1.5 channel blockers for the treatment of atrial fibrillation.
New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition
Roy, Pierre-Philipe,Faye, Diene,Blanchard, Sébastien,Cormier, Marc,Doiron, Jérémie A.,Surette, Marc E.,Touaibia, Mohamed
, (2017/05/29)
Leukotrienes are biosynthesized by the conversion of arachidonic acid by 5-Lipoxygenase and play a key role in many inflammatory disorders. Inspired by caffeic acid phenylethyl ester (CAPE) (2) and an analog carrying a triazole substituted by cinnamoyl an
RAFT polymerization of bromotyramine-based 4-acryloyl-1,2,3-triazole: A functional monomer and polymer family through click chemistry
Andjouh, Sofyane,Bressy, Christine,Blache, Yves
, p. 14496 - 14504 (2016/02/19)
Four new functional acryloyl-triazole monomers derived from bromotyramine were successfully synthesized. These monomers were prepared in an efficient way from organic azides and propargyl acrylate via a copper catalyzed 1,3-dipolar cycloaddition. Polymers containing bromotyramine as a pendant group were obtained via reversible addition-fragmentation chain transfer (RAFT) polymerization. The influence of the chain transfer agent (CTA), solvent, temperature and the length of the linker between the triazole and bromotyramine groups on the polymerization kinetics was studied. It was found that triazoles containing acrylate monomers are characterized by fast polymerization and polymers with controlled molar masses (20 000 g mol-1) and low dispersities (DM 1.5) can be prepared. Glass transition temperatures of these acrylic polymers ranged from 48 °C to 20 °C by controlling the length of the linker between the bromotyramine side groups and the backbone.
Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries
Suzuki, Takayoshi,Ota, Yosuke,Ri, Masaki,Bando, Masashige,Gotoh, Aogu,Itoh, Yukihiro,Tsumoto, Hiroki,Tatum, Prima R.,Mizukami, Tamio,Nakagawa, Hidehiko,Iida, Shinsuke,Ueda, Ryuzo,Shirahige, Katsuhiko,Miyata, Naoki
, p. 9562 - 9575 (2013/01/16)
To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.
Formation and stability of the 4-methoxyphenonium ion in aqueous solution
Tsuji, Yutaka,Hara, Daisuke,Hagimoto, Rui,Richard, John P.
supporting information; experimental part, p. 9568 - 9571 (2012/01/02)
The reaction of 2-methoxyphenylethyl tosylate (MeO-1-Ts) is first-order in [N3-]. A carbon-13 NMR analysis of the products of the reactions of MeO-1-[α-13C]Ts shows the formation of MeO-1-[β-13C]OH and MeO-1-[β-13C]N3 from the trapping of a symmetrical 4-methoxyphenonium ion reaction intermediate 2+. An analysis of the rate and product data provides a value of kaz/ks = 83 M- 1 for partitioning of 2 + between addition of azide ion and solvent. These data set a limit for the lifetime of 2+ in aqueous solution.
A radical procedure for the anti-markovnikov hydroazidation of alkenes
Kapat, Ajoy,Koenig, Andreas,Montermini, Florian,Renaud, Philippe
supporting information; experimental part, p. 13890 - 13893 (2011/10/31)
A one-pot procedure for the efficient hydroazidation of alkenes involving hydroboration with catecholborane followed by reaction with benzenesulfonyl azide in the presence of a radical initiator is described. The regioselectivity is controlled by the hydroboration step and corresponds in most cases to an anti-Markovnikov regioselectivity. This procedure is applicable to a wide range of alkenes and gives excellent results with 1,2-disubstituted and trisubstituted alkenes.
Design, synthesis, and structure-activity relationships of novel 2-substituted pyrazinoylguanidine epithelial sodium channel blockers: Drugs for cystic fibrosis and chronic bronchitis
Hirsh, Andrew J.,Molino, Bruce F.,Zhang, Jianzhong,Astakhova, Nadezhda,Geiss, William B.,Sargent, Bruce J.,Swenson, Brian D.,Usyatinsky, Alexander,Wyle, Michael J.,Boucher, Richard C.,Smith, Rick T.,Zamurs, Andra,Johnson, M. Ross
, p. 4098 - 4115 (2007/10/03)
Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent short-circuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloríde and displayed the lowest IC50 value ever reported for an ENaC blocker.
