397843-71-9Relevant articles and documents
Thieno [3, 2 - c] pyridine compound, its preparation method and application
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Paragraph 0237; 0238; 0239, (2018/09/02)
The invention relates to a thieno-[3,2-c] pyridine type compound and an application thereof. The compound has a structure shown by a formula (I) in the specification. The compound of which the structure is shown by the formula (I), provided by the invention has a very good effect of inhibiting the activity of Bruton kinase. The invention also relates to the application of the compound in preventing and/or treating diseases which are improved by virtue of BTK (Bruton tyrosine kinase) activity inhibition.
Discovery of thieno[3,2-c]pyridin-4-amines as novel Bruton's tyrosine kinase (BTK) inhibitors
Zhao, Xinge,Xin, Minhang,Wang, Yazhou,Huang, Wei,Jin, Qiu,Tang, Feng,Wu, Gang,Zhao, Yong,Xiang, Hua
, p. 6059 - 6068 (2015/11/11)
A novel series of BTK inhibitors bearing thieno[3,2-c]pyridin-4-amine framework as the core scaffold were designed, synthesized and well characterized. In this paper, twenty one compounds displayed variant inhibitory activities against BTK in vitro, and c
Universal solid-phase approach for the immobilization, derivatization, and resin-to-resin transfer reactions of boronic acids
Gravel, Michael,Thompson, Kim A.,Zak, Mark,Berube, Christian,Hall, Dennis G.
, p. 3 - 15 (2007/10/03)
Boronic acid-containing molecules are employed in a broad range of biological, medicinal, and synthetic applications. These compounds, however, tend to be difficult to handle by solution-phase methods. Herein, this problem is addressed with the development of the first general solid-phase approach for the derivatization of functionalized boronic acids. This approach is based on the use of a diethanolamine resin anchor that facilitates boronic acid immobilization by avoiding the need for exhaustive removal of water in the esterification process. The immobilization of a wide variety of boronic acids onto N,N-diethanolaminomethyl polystyrene (DEAM-PS, 1) can be performed within minutes by simple stirring in anhydrous solvents at room temperature. Evidence for the formation of a bicyclic diethanolamine boronate with putative N-B coordination was shown by 1H NMR analysis of DEAM-PS-supported p-tolylboronic acid. The hydrolytic cleavage of the same model boronic acid from the DEAM-PS resin was studied by UV spectroscopy. Hydrolysis and attachment were shown to occur under a rapidly attained equilibrium, and a large excess of water (> 32 equiv) is required to effect a practically quantitative release of boronic acids from DEAM-PS. Despite their relative sensitivity to water and alcohols, DEAM-PS-bound arylboronic acids functionalized with a formyl, a bromomethyl, a carboxyl, or an amino group can be transformed in good to excellent yields into a wide variety of amines, amides, anilides, and ureas, respectively. Ugi multicomponent reactions on DEAM-PS-supported aminobenzeneboronic acids, derivatization of multifunctional arylboronic acids, and sequential reactions can also be carried out efficiently. These new DEAM-PS-supported arylboronic acids can be employed directly into resin-to-resin transfer reactions (RRTR). This type of multiresin process helps eliminate time-consuming cleavage and transfer operations, thereby considerably simplifying the outlook of combinatorial library synthesis by manual or automated means. This concept was illustrated by a set of optimized procedures for the Suzuki cross-coupling and the borono-Mannich reactions.
