137741-26-5Relevant academic research and scientific papers
A Synthesis of (+)-7-Epiaustraline and (-)-7-Epialexine
Pearson, William H.,Hines, Jennifer V.
, p. 5513 - 5516 (1991)
Reductive cyclization of the azido epoxides 19α and 19β followed by deprotection afforded the HIV inhibitor (+)-7-epiaustraline 7 and (-)-7-epialexine 9.The formation of 7 proceeded with an unusual inversion of configuration at C-7.Key Words: (+)-7-Epiaus
Synthesis and inhibition study of bicyclic iminosugar-based alkaloids, scaffolds, and libraries towards glucosidase
Cheng, Wei-Chieh,Guo, Chih-Wei,Lin, Cheng-Kun,Jiang, Yu-Ruei
, p. 403 - 411 (2015/04/22)
A small library of bicyclic iminosugar-based alkaloids and scaffolds possessing a polyhydroxylated pyrrolidine and a varied ring skeleton have been synthesized. Through rapid diversification of the scaffold via an amide coupling with random carboxylic acids, structurally diverse bicyclic iminosugar-based libraries were prepared with substituent diversity, core diversity, and configurational diversity. This discovery process allowed us to efficiently sieve out potent and specific glycosidase inhibitors, and a bicyclic, conformationally restricted iminosugar was demonstrated to be more potent than the monocyclic ones in this study. The most potent and selective inhibitor discovered was found to have a Ki value of 71 nM against α-glucosidase.
Synthesis and glycosidase inhibition of Australine and its fluorinated derivatives
Li, Yi-Xian,Shimada, Yousuke,Sato, Kasumi,Kato, Atsushi,Zhang, Wei,Jia, Yue-Mei,Fleet, George W. J.,Xiao, Min,Yu, Chu-Yi
supporting information, p. 716 - 719 (2015/03/05)
Australine (1), 7-epi-australine (2), and their C-7-fluorinated derivatives 4 and 5 have been synthesized efficiently from d-arabinose-derived cyclic nitrone 11. Fluorination at the C-7 position enhanced the inhibition against A. niger ?±-glucosidase, and
Stereocomplementary routes to hydroxylated nitrogen heterocycles: Total syntheses of casuarine, Australine, and 7-epi-Australine
Parmeggiani, Camilla,Cardona, Francesca,Giusti, Leonardo,Reissig, Hans-Ulrich,Goti, Andrea
, p. 10595 - 10604 (2013/08/23)
Addition of lithiated 1-benzyloxyallene to a D-arabinose-derived cyclic nitrone occurred with perfect diastereoselectivity furnishing a bicyclic 1,2-oxazine derivative, which is an excellent precursor for pyrrolizidine alkaloids hydroxylated at C-7 with o
