874916-37-7Relevant academic research and scientific papers
Design, synthesis, biological evaluations, molecular docking, and in vivo studies of novel phthalimide analogs
Zahran, Magdy A. H.,El-Aarag, Bishoy,Mehany, Ahmed B. M.,Belal, Amany,Younes, Ali S.
, (2018)
A series of novel phthalimide analogs containing an indole or brominated indole moiety were synthesized and their antimicrobial activity was evaluated. Compound 8 showed a broad spectrum activity, revealing 53–67% of erythromycin activity on the tested ba
Access to Spirocyclized Oxindoles and Indolenines via Palladium-Catalyzed Cascade Reactions of Propargyl Carbonates with 2-Oxotryptamines and Tryptamines
Nibbs, Antoinette E.,Montgomery, Thomas D.,Zhu, Ye,Rawal, Viresh H.
, p. 4928 - 4941 (2015/06/02)
(Chemical Equation Presented). Reported here are methods for the direct construction of a range of spirocyclized oxindoles and indolenines in good to excellent yields. Specifically, we report the palladium-catalyzed reactions of oxindoles and indoles, both functioning as bis-nucleophiles, with propargyl carbonates to afford spirocyclic products having an exocyclic double bond on the newly formed ring. The reaction proceeds through a process wherein the first nucleophilic unit on the oxindole or indole reacts with an allenyl-palladium species, formed from oxidative addition of Pd(0) to propargyl carbonates, to generate a π-allyl palladium intermediate that then reacts further with the second nucleophilic component of the oxindole or indole. The cascade process forges two bonds en route to spirocyclized oxindole and indolenine products. The use of chiral phosphines renders the cyclization sequence enantioselective, providing spirocyclic products with modest to good enantioselectivities.
Structure-Activity Relationships of Novel Tryptamine-Based Inhibitors of Bacterial Transglycosylase
Sosi?, Izidor,Anderluh, Marko,Sova, Matej,Gobec, Martina,Mlinari? Ra??an, Irena,Derouaux, Adeline,Amoroso, Ana,Terrak, Mohammed,Breukink, Eefjan,Gobec, Stanislav
supporting information, p. 9712 - 9721 (2016/01/12)
Penicillin-binding proteins represent well-established, validated, and still very promising targets for the design and development of new antibacterial agents. The transglycosylase domain of penicillin-binding proteins is especially important, as it catalyzes polymerization of glycan chains, using the peptidoglycan precursor lipid II as a substrate. On the basis of the previous discovery of a noncovalent small-molecule inhibitor of transglycosylase activity, we systematically explored the structure-activity relationships of these tryptamine-based inhibitors. The main aim was to reduce the nonspecific cytotoxic properties of the initial hit compound and concurrently to retain the mode of its inhibition. A focused library of tryptamine-based compounds was synthesized, characterized, and evaluated biochemically. The results presented here show the successful reduction of the nonspecific cytotoxicity, and the retention of the inhibition of transglycosylase enzymatic activity, as well as the ability of these compounds to bind to lipid II and to have antibacterial actions.
Facile construction of the pentacyclic framework of subincanadine B. Synthesis of 20-deethylenylated subincanadine B and 19,20-dihydrosubincanadine B
Liu, Yanqin,Luo, Shengjun,Fu, Xingnian,Fang, Fang,Zhuang, Zeyang,Xiong, Wanting,Jia, Xueshun,Zhai, Hongbin
, p. 115 - 118 (2007/10/03)
(Chemical Equation Presented) We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine B, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.
