77117-15-8Relevant articles and documents
Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives
Cao, Lian-Gong,Cao, Zhi-Ling,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Lu, Xing,Shao, Zhong-Bai,Shi, Da-Hua,Wang, Lei,Wang, You-Xian
, p. 359 - 364 (2020/12/28)
Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.
Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety
Ngoc Toan, Vu,Dinh Thanh, Nguyen,Minh Tri, Nguyen,Thi Thu Huong, Nguyen
supporting information, (2020/11/20)
Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).
Green and Rapid Access to Benzocoumarins via Direct Benzene Construction through Base-Mediated Formal [4+2] Reaction and Air Oxidation
Mou, Chengli,Zhu, Tingshun,Zheng, Pengcheng,Yang, Song,Song, Bao-An,Chi, Yonggui Robin
supporting information, p. 707 - 712 (2016/03/09)
Benzocoumarin is an important structural motif widely found in natural products and synthetic molecules. Traditional methods for the synthesis of benzocoumarins and their derivatives require multiple steps, typically with an intramolecular ester forming reaction to make the lactone ring as the last step. Another major method involves transition metal-catalyzed coupling or carbon-hydrogen bond activation reactions starting with pre-existing aryl frameworks in the substrates. Here we report a new strategy for the green and rapid access to benzocoumarins and their derivatives. Our method uses readily available unsaturated aldehydes and coumarins as the substrates and air as the green oxidant. The overall reaction proceeds through a formal [4+2] process to construct a new benzene ring and thus to afford benzocoumarins in essentially a single step. No metal catalysts were used; no toxic or expensive reagents were involved. The power of our new approach is further demonstrated in a concise formal total synthesis of cannabinol, a bioactive natural product.
