65783-21-3Relevant academic research and scientific papers
One-Pot Evolution of Ageladine A through a Bio-Inspired Cascade towards Selective Modulators of Neuronal Differentiation
Iwata, Takayuki,Otsuka, Satoshi,Tsubokura, Kazuki,Kurbangalieva, Almira,Arai, Daisuke,Fukase, Koichi,Nakao, Yoichi,Tanaka, Katsunori
, p. 14707 - 14716 (2016/10/03)
A bio-inspired cascade reaction has been developed for the construction of the marine natural product ageladine A and a de novo array of its N1-substituted derivatives. This cascade features a 2-aminoimidazole formation that is modeled after an arginine post-translational modification and an aza-electrocyclization. It can be effectively carried out in a one-pot procedure from simple anilines or guanidines, leading to structural analogues of ageladine A that had been otherwise synthetically inaccessible. We found that some compounds out of this structurally novel library show a significant activity in modulating the neural differentiation. Namely, these compounds selectively activate or inhibit the differentiation of neural stem cells to neurons, while being negligible in the differentiation to astrocytes. This study represents a successful case in which the native biofunction of a natural product could be altered by structural modifications.
Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2
Blake, James F.,Gaudino, John J.,De Meese, Jason,Mohr, Peter,Chicarelli, Mark,Tian, Hongqi,Garrey, Rustam,Thomas, Allen,Siedem, Christopher S.,Welch, Michael B.,Kolakowski, Gabrielle,Kaus, Robert,Burkard, Michael,Martinson, Matthew,Chen, Huifen,Dean, Brian,Dudley, Danette A.,Gould, Stephen E.,Pacheco, Patricia,Shahidi-Latham, Sheerin,Wang, Weiru,West, Kristina,Yin, Jianping,Moffat, John,Schwarz, Jacob B.
, p. 2635 - 2639 (2014/06/09)
The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts.
Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2
Blake, James F.,Gaudino, John J.,De Meese, Jason,Mohr, Peter,Chicarelli, Mark,Tian, Hongqi,Garrey, Rustam,Thomas, Allen,Siedem, Christopher S.,Welch, Michael B.,Kolakowski, Gabrielle,Kaus, Robert,Burkard, Michael,Martinson, Matthew,Chen, Huifen,Dean, Brian,Dudley, Danette A.,Gould, Stephen E.,Pacheco, Patricia,Shahidi-Latham, Sheerin,Wang, Weiru,West, Kristina,Yin, Jianping,Moffat, John,Schwarz, Jacob B.
, p. 2635 - 2639 (2015/02/19)
The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts.
Synthesis and biological activity of 2-anilino-4-(1H-pyrrol-3-yl) pyrimidine CDK inhibitors
Wang, Shudong,Wood, Gavin,Meades, Christopher,Griffiths, Gary,Midgley, Carol,McNae, Iain,McInnes, Campbell,Anderson, Sian,Jackson, Wayne,Mezna, Mokdad,Yuill, Rhoda,Walkinshaw, Malcolm,Fischer, Peter M.
, p. 4237 - 4240 (2007/10/03)
A series of 2-anilino-4-(1H-pyrrol-3-yl)pyrimidines were prepared and evaluated for their ability to inhibit cyclin-dependent kinases (CDKs). A number of analogues were found to be potent CDK2 and CDK4 inhibitors and to exhibit anti-proliferative activity
Solid-phase synthesis of N-aryl-N′-carboalkoxy guanidines by the mitsunobu reaction of Fmoc-guanidines
Robinson, Dale E.,Seth, Punit P.,Jefferson, Elizabeth A.
, p. 2743 - 2749 (2007/10/03)
A new method for the solid-phase synthesis of N-aryl-N′-carboalkoxy guanidines is described. Aromatic amines were reacted with Fmoc-isothiocyanate to provide Fmoc-thioureas, which were coupled with Rink amide resin to provide the corresponding resin-bound Fmoc-guanidines. Subsequent Mitsunobu alkylation with a variety of alcohols delivered N-aryl-N′ carboalkoxy guanidines in good to high purity after resin cleavage.
