67713-23-9Relevant articles and documents
Design, synthesis and structure of a frustrated benzoxaborole and its applications in the complexation of amines, amino acids, and protein modification
Bhangu, Jasmine,Hall, Dennis G.,Whittal, Randy M.
, p. 3492 - 3500 (2020)
This study describes the design and synthesis of arylboronic acid 2, the first example of a permanently open "frustrated" benzoxaborole, along with an exploration of its application in bioconjugation. An efficient and high yielding seven-step synthesis was optimized. NMR experiments confirmed that compound 2 exists in the open ortho-hydroxyalkyl arylboronic acid structure 2-I, a form that is effectively prevented to undergo a dehydrative cyclization as a result of unfavorable geometry. Compound 2-I conjugates effectively with amines to form stable hemiaminal ether structures, including a highly effective reaction with lysozyme. Complexation with cysteine induces an open structure containing a free hydroxymethyl arm, with the amino and thiol groups reacting preferentially with the formyl group to form a N,S-acetal.
Functional Porphyrinic Metal–Organic Framework as a New Class of Heterogeneous Halogen-Bond-Donor Catalyst
Chen, Yu-Sheng,Cheng, Qigan,Ma, Shengqian,Nafady, Ayman,Shan, Chuan,Wojtas, Lukasz,Zhang, Weijie,Zhang, X. Peter
supporting information, p. 24312 - 24317 (2021/10/04)
Biomimetic metal-organic frameworks have attracted great attention as they can be used as bio-inspired models, allowing us to gain important insights into how large biological molecules function as catalysts. In this work, we report the synthesis and utilization of such a metal-metalloporphyrin framework (MMPF) that is constructed from a custom-designed ligand as an efficient halogen bond donor catalyst for Diels–Alder reactions under ambient conditions. The implementation of fabricated halogen bonding capsule as binding pocket with high-density C?Br bonds enabled the use of halogen bonding to facilitate organic transformations in their three-dimensional cavities. Through combined experimental and computational studies, we showed that the substrate molecules diffuse through the pores of the MMPF, establishing a host-guest system via the C?Br???π interaction. The formation of halogen bonds is a plausible explanation for the observed boosted catalytic efficiency in Diels–Alder reactions. Moreover, the unique capability of MMPF highlights new opportunities in using artificial non-covalent binding pockets as highly tunable and selective catalytic materials.
ISOCHROMAN COMPOUNDS AND USES THEREOF
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Paragraph 0387; 0389-0390, (2019/02/15)
Compounds of Formula I are described, as are pharmaceutical compositions containing such compounds. Methods of treating neurological or psychiatric diseases and disorders in a subject in need are also disclosed.
