147167-25-7Relevant academic research and scientific papers
The Renaissance of an Old Problem: Highly Regioselective Carboxylation of 2-Alkynyl Bromides with Carbon Dioxide
Miao, Bukeyan,Li, Gen,Ma, Shengming
, p. 17224 - 17228 (2015)
A steric effect-controlled, zinc-mediated carboxylation of different 2-alkynyl bromides under an atmospheric pressure of CO2 has been developed by careful tuning of different reaction parameters, including the metal, solvent, temperature, and additive. 2-Substituted 2,3-allenoic acids were afforded from primary 2-alkynyl bromides, whereas the carboxylation of secondary 2-alkynyl bromides yielded 3-alkynoic acids in decent yields. A rationale for the observed regioselectivity has been proposed.
Small-molecule inhibitors of protein geranylgeranyltransferase type I
Castellano, Sabrina,Fiji, Hannah D. G.,Kinderman, Sape S.,Watanabe, Masaru,De Leon, Pablo,Tamanoi, Fuyuhiko,Kwon, Ohyun
, p. 5843 - 5845 (2008/03/14)
Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics. Copyright
Cycloadditions, XX, Thermally Induced Intramolecular Reactions of 2-Methyl-2,3-butadienamides
Himbert,Gerhard,Schlindwein, Hans-Juergen
, p. 1785 - 1794 (2007/10/02)
The 2-methyl-2,3-butadienamides 4a-m are directly synthesized by the reaction of the corresponding allenic acid chloride 2 with the secondary amines 3.At heating, 4a-j undergo the intramolecular Diels-Alder reaction, by using their ω-standing double bond and the ?-system of the directly bonded phenyl groups or of the "methylenic" bonded arenes of furans.Thereby the tricycles 6a-g (bearing five-membered lactam moieties) and/or the tricycles 7-9 (bearing six-membered lactam moieties) are formed.The influence of the geminal methyl group on the chemoselectivity and on the velocity of the IMDA reactions is investigated.The N-allyl derivatives of 4 (s. 4l and m) form the bicycles 10 by intramolecular -Cycloaddition. Key words: 2-Methyl-2,3-butadienamides, Intramolecular - and -Cycloadditions
