10451-00-0Relevant articles and documents
Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry
Huang, Boxuan,Li, Weijia,Mu, Yu,Shao, Liang,Su, Yangqing,Sun, Mengsi,Xu, Huan,Yang, Fan,Yu, Fei,Zhang, Jihong,Zhang, Yuan
, p. 1759 - 1765 (2021/11/18)
Influenza is a major threat to millions of people worldwide. Entry inhibitors are of particular interest for the development of novel therapeutic strategies for influenza. We have previously discovered oleanolic acid (OA) to be a mild influenza hemagglutinin (HA) inhibitor. In this work, inspired by the 3D structure of HA as a homotrimeric receptor, we designed and synthesized 15 OA trimers with different linkers and central region via the copper-catalyzed azide-alkyne cycloaddition reaction. All of the OA trimers were evaluated for their antiviral activities in vitro, and 12c, 12e, 13c, and 13d were observed to exhibit robust potency (IC50 in the submicromolar range) against influenza A/WSN/33 (H1N1) virus that was stronger than that observed with oseltamivir. In addition, these compounds also displayed strong biological activity against A/Hong Kong/4801/2014 and B/Sichuan/531/2018 (BV). The results of hemagglutination inhibition assays and surface plasmon resonance binding assays suggest that these OA trimers may interrupt the interaction between the HA protein of influenza virus and the host cell sialic acid receptor, thus blocking viral entry. These findings highlight the utility of multivalent OA conjugates to enhance the ligand-target interactions in anti-influenza virus drug design and are also helpful for studying antiviral drugs derived from natural products.
Stereoselective spirolactam synthesis via palladium catalyzed arylative allene carbocyclization cascades
Li, Meiling,Dixon, Darren J.
supporting information; experimental part, p. 3784 - 3787 (2010/11/04)
A diastereoselective arylative carbocyclization of pro-nucleophile-linked allenes with aryl and heteroaryl halides to provide spirocyclic lactam products with moderate to high diastereoselectivities and good yields under Pd(0) catalysis is reported. Being operationally simple and tolerant of multiple points of diversity, this complexity building reaction cascade, in which two new carbon-carbon bonds and one new heterocyclic ring are created, should be of high value in both complex natural product synthesis as well as compound library synthesis.
Et2Zn-catalyzed intramolecular hydroamination of alkynyl sulfonamides and the related tandem cyclization/addition reaction
Yin, Yan,Ma, Wenying,Chai, Zhuo,Zhao, Gang
, p. 5731 - 5736 (2008/02/09)
(Chemical Equation Presented) Intramolecular hydroamination of alkynyl amides was effected by a catalytic amount of Et2Zn (20 mol %) to form indole derivatives, and a tandem cyclization/nucleophilic addition procedure involving reaction of the indole zinc salt intermediate with acid chlorides or halides was developed to provide an efficient approach to C3-substituted indole derivatives when an excess of Et2Zn (120 mol %) was used.
