66362-36-5Relevant academic research and scientific papers
Construction of N-Heterocyclic Systems Containing a Fully Substituted Allylic Carbon by Palladium/Phosphine Catalysis
Ogiwara, Yohei,Suzuki, Yui,Sato, Kazuya,Sakai, Norio
supporting information, p. 6965 - 6969 (2018/11/21)
The unique cyclization of benzamide derivatives that contain an alkyne by a Pd(0)/dialkyl(biaryl)phosphine catalytic system is reported. The reaction efficiently provides a variety of six-membered N-heterocyclic compounds that contain a fully substituted carbon center without the need for a stoichiometric additive. Mechanistic studies suggest that this unprecedented cyclization starts with the cleavage of a propargylic C-O bond, and a 1,3-diene has been identified as a relevant intermediate.
Synthesis and biological evaluation of JL-A7 derivatives as potent ABCB1 inhibitors
Pan, Miaobo,Cui, Jian,Jiao, Lei,Ghaleb, Hesham,Liao, Chen,Zhou, Jiaqi,Kairuki, Mutta,Lin, Haiyan,Huang, Wenlong,Qian, Hai
, p. 4194 - 4202 (2017/07/05)
Cancer chemotherapy failure is often due to the overexpression of ATP-binding cassette (ABC) transporters (particularly ABCB1), resulting in a variety of structurally and pharmacologically unrelated drugs efflux. The multidrug resistance (MDR) phenomenon could be reversed by ABCB1 inhibitors. Now, JL-A7 as the lead compound based on a triazol-N-ethyl-tetrahydroisoquinoline scaffold, 18 compounds were designed and synthesized. Substitution in para positions yielded high activities toward ABCB1. Moreover, compound 5 could effectively block the drug efflux function of ABCB1 and increase the accumulation of anti-cancer drugs to achieve effective treatment concentration in MDR cells.
6,7-Dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinolines as superior reversal agents for P-glycoprotein-mediated multidrug resistance
Liu, Baomin,Qiu, Qianqian,Zhao, Tianxiao,Jiao, Lei,Li, Yunman,Huang, Wenlong,Qian, Hai
, p. 336 - 344 (2015/02/05)
P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major obstacle for successful cancer chemotherapy. Based on our previous study, 17 novel compounds with the 6,7-dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinoline scaffold were designed and synthesized. Among them, 2-[(1-{4-[2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]phenyl}-1H-1,2,3-triazol-4-yl)methoxy]-N-(p-tolyl)-benzamide (compound 7h) was identified as a potent modulator of P-gp-mediated MDR, with high potency (EC50 = 127.5 ± 9.1 nM), low cytotoxicity (TI > 784.3), and long duration (> 24 h) in reversing doxorubicin (DOX) resistance in K562/A02 cells. Compound 7h also enhanced the effects of other MDR-related cytotoxic agents (paclitaxel, vinblastine, and daunorubicin), increased the accumulation of DOX and blocked P-gp-mediated rhodamine 123 efflux function in K562/A02 MDR cells. Moreover, 7h did not have any effect on cytochrome (CYP3A4) activity. These results indicate that 7h is a relatively safe modulator of P-gp-mediated MDR that has good potential for further development.
Carbon-Carbon Bond Formation via Intramolecular Cycloadditions: Use of the Thiocarbonyl Ylide Dipole in anhydro-4-Hydroxythiazolium Hydroxides
Potts, Kevin T.,Dery, Maurice O.,Juzukonis, Walter A.
, p. 1077 - 1088 (2007/10/02)
The mesoionic systems resulting from the introduction of 2-(allyloxy)phenyl substituents into the 2-, 3-, and 5-positions of anhydro-4-hydroxythiazolium hydroxide undergo intramolecular cycloaddition under different reaction conditions, the ease of cycloa
Intramolecular 1,4-Dipolar Cycloadditions utilizing Heteroaromatic Betaines
Potts, Kevin T.,Dery, Maurice O.
, p. 563 - 565 (2007/10/02)
anhydro-2-(2-Allyloxyphenyl)-3,5-diphenyl-4-hydroxy-6-oxo-1,3-thiazinium hydroxide and the corresponding ethynyl derivative underwent ready thermal 1,4-dipolar cycloaddition to give a 1:1-cycloadduct (whose structure was determined by X-ray crystallograph
