115833-93-7Relevant articles and documents
1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration
Jeon, Young-Kyo,Kim, Won-Suk
supporting information, p. 7545 - 7549 (2021/10/12)
The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%.
Squarylium compound
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Paragraph 0100; 0101; 0103, (2018/08/30)
PROBLEM TO BE SOLVED: To provide a squarylium compound excellent in stability in a polar solvent, a solution containing the same and a resin composition. SOLUTION: There is provided a squarylium compound represented by the following formula (1), where Rs
Dipyrimidine amines: A novel class of chemokine receptor type 4 antagonists with high specificity
Zhu, Aizhi,Zhan, Weiqiang,Liang, Zhongxing,Yoon, Younghyoun,Yang, Hua,Grossniklaus, Hans E.,Xu, Jianguo,Rojas, Mauricio,Lockwood, Mark,Snyder, James P.,Liotta, Dennis C.,Shim, Hyunsuk
experimental part, p. 8556 - 8568 (2011/02/28)
The C-X-C chemokine receptor type 4 (CXCR4)/stromal cell derived factor-1 (SDF-1 or CXCL12) interaction and the resulting cell signaling cascade play a key role in metastasis and inflammation. On the basis of the previously published CXCR4 antagonist 5 (WZ811), a series of novel nonpeptidic anti-CXCR4 small molecules have been designed and synthesized to improve potency. Following a structure-activity profile around 5, more advanced compounds in the N,N-(1, 4-phenylenebis(methylene)) dipyrimidin-2-amines series were discovered and shown to possess higher CXCR4 binding potential and specificity than 5. Compound 26 (508MCl) is the lead compound and exhibits subnanomolar potency in three in vitro assays including competitive binding, Matrigel invasion and Gαi cyclic adenosine monophosphate (cAMP) modulation signaling. Furthermore, compound 26 displays promising effects by interfering with CXCR4 function in three mouse models: paw inflammation, Matrigel plug angiogenesis, and uveal melanoma micrometastasis. These data demonstrate that dipyrimidine amines are unique CXCR4 antagonists with high potency and specificity.