33675-75-1Relevant academic research and scientific papers
Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization
Ansel, Annabel Q.,Montgomery, John
, p. 8538 - 8543 (2020/11/12)
A one-pot multicomponent copper-catalyzed protocol for borylation/ortho-cyanation of styrene derivatives followed by a Suzuki-Miyaura coupling provides a platform to explore the factors that control the selectivity between distal or proximal functionalization of arenes. The development of divergent nitrile-directed C-H functionalization (acetoxylation, pivalation, and methoxylation) offers an effective approach to rapidly increase synthetic complexity. Finally, the development of a mild reductive decyanation allows a traceless method to access functionalized biaryl motifs.
Topographical Mapping of Isoform-Selectivity Determinants for J-Channel-Binding Inhibitors of Sphingosine Kinases 1 and 2
Adams, David R.,Tawati, Salha,Berretta, Giacomo,Rivas, Paula Lopez,Baiget, Jessica,Jiang, Zhong,Alsfouk, Aisha,Mackay, Simon P.,Pyne, Nigel J.,Pyne, Susan
, p. 3658 - 3676 (2019/04/26)
Sphingosine kinase enzymes (SK1 and SK2) catalyze the conversion of sphingosine into sphingosine 1-phosphate and play a key role in lipid signaling and cellular responses. Mapping of isoform amino acid sequence differences for SK2 onto the recently available crystal structures of SK1 suggests that subtle structural differences exist in the foot of the lipid-binding "J-channel" in SK2, the structure of which has yet to be defined by structural biology techniques. We have probed these isoform differences with a ligand series derived from the potent SK1-selective inhibitor, PF-543. Here we show how it is possible, even with relatively conservative changes in compound structure, to systematically tune the activity profile of a ligand from ca. 100-fold SK1-selective inhibition, through equipotent SK1/SK2 inhibition, to reversed 100-fold SK2 selectivity, with retention of nanomolar potency.
Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
Moodie, Lindon W. K.,Trepos, Rozenn,Cervin, Gunnar,Brathen, Kari Anne,Lindgard, Bente,Reiersen, Rigmor,Cahill, Patrick,Pavia, Henrik,Hellio, Claire,Svenson, Johan
, p. 2001 - 2011 (2017/08/04)
The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn
Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues
Wilhelm, Anke,Kendrekar, Pravin,Noreljaleel, Anwar E. M.,Abay, Efrem T.,Bonnet, Susan L.,Wiesner, Lubbe,De Kock, Carmen,Swart, Kenneth J.,Van Der Westhuizen, Jan Hendrik
, p. 1848 - 1858 (2015/09/08)
(Chemical Equqation Presented). A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 μM. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.
Homo- and hetero-oxidative coupling of benzyl anions
Blangetti, Marco,Fleming, Patricia,O'Shea, Donal F.
experimental part, p. 2870 - 2877 (2012/04/23)
The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.
Syntheses and Platelet Aggregation Inhibitory and Antithrombotic Properties of ethyl>benzenes
Kikumoto, Ryoji,Hara, Hiroto,Ninomiya, Kunihiro,Osakabe, Masanori,Sugano, Mamoru,et al.
, p. 1818 - 1823 (2007/10/02)
A series of ethyl>benzene derivatives were synthesized and evaluated for their ability to inhibit collagen-induced platelet aggregation in vitro and to protect experimantal thrombosis in mice.The results showed that the compounds were in vitro inhibitors of collagen-induced platelet aggregation.Most of them were also effective in the mouse antithrombotic assay.The compounds were found to be potent antagonists to S2 serotonergic receptor, and good correlation (r = 0.85) between their S2 serotonergic receptor antagonism and their potency as platelet antiaggregatory drugs was observed.Among the compounds studied, monophenoxy>methyl>ethyl>succinate hydrochloride (12b, MCI-9042) was selected for further pharmacological and toxicological evaluation.
Preparation and Reactions of Dianions from the Cresols
Bates, Robert B.,Siahaan, Teruna J.
, p. 1432 - 1434 (2007/10/02)
With n-BuLi/KO-t-Bu, protons are removed from the hydroxyl and methyl groups of cresols 5 to give dianions 6 in yields of 85percent (ortho), 95percent (meta), and 42percent (para).These dianions react with alkyl halides, Me3SiCl, Bu3SnCl, CO2, and oxidizing agents at carbon only and with dialkyl sulfates at both carbon and oxygen.Thus phenol derivatives bearing primary alkyl groups can be prepared from the corresponding methylphenols via dianions 6.
