50622-52-1Relevant academic research and scientific papers
Identification of N-Benzyl 3,5-Dinitrobenzamides Derived from PBTZ169 as Antitubercular Agents
Li, Linhu,Lv, Kai,Yang, Yupeng,Sun, Jingquan,Tao, Zeyu,Wang, Apeng,Wang, Bin,Wang, Hongjian,Geng, Yunhe,Liu, Mingliang,Guo, Huiyuan,Lu, Yu
supporting information, p. 741 - 745 (2018/07/05)
A series of benzamide scaffolds were designed and synthesized by the thiazinone ring opening of PBTZ169, and N-benzyl 3,5-dinitrobenzamides were finally identified as anti-TB agents in this work. 3,5-Dinitrobenzamides D5, 6, 7, and 12 exhibit excellent in vitro activity against the drug susceptive Mycobacterium tuberculosis H37Rv strain (MIC: 0.0625 μg/mL) and two clinically isolated multidrug-resistant strains (MIC 0.016-0.125 μg/mL). Compound D6 displays acceptable safety and better pharmacokinetic profiles than PBTZ169, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.
Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives
Lv, Kai,Li, Linhu,Wang, Bo,Liu, Mingliang,Wang, Bin,Shen, Weiyi,Guo, Huiyuan,Lu, Yu
, p. 117 - 125 (2017/06/05)
We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.
Identification of N-(2-Phenoxyethyl)imidazo[1,2-a]pyridine-3-carboxamides as New Antituberculosis Agents
Wu, Zhaoyang,Lu, Yu,Li, Linhu,Zhao, Rui,Wang, Bin,Lv, Kai,Liu, Mingliang,You, Xuefu
supporting information, p. 1130 - 1133 (2016/12/16)
A series of imidazo[1,2-a]pyridine carboxamides (IPAs) bearing an N-(2-phenoxyethyl) moiety was designed and synthesized as new antitubercular agents. Seven 2,6-dimethyl IPAs demonstrated excellent in vitro activity (MIC: 0.025-0.054 μg/mL) against the drug susceptive H37Rv strain and two clinically isolated multidrug-resistant Mycobacterium tuberculosisstrains. Compound 10j displayed acceptable safety and pharmacokinetic properties, opening a new direction for further development.
New diketopyrrolopyrrole (DPP) derivative as fluorescent probe for Zn 2+
Zhang, Guanjun,Bi, Shiming,Song, Longfeng,Wang, Feng,Yu, Jianjun,Wang, Limin
, p. 779 - 786 (2013/09/12)
Abstract New turn-on fluorescent probe DPPL2, was rationally designed and synthesized based on the skeleton of diketopyrrolopyrrole (DPP), which presented sensitivity, selectivity for Zn2+ over other metal ions except some disturbance with Cd2+. Particularly, results demonstrated fluorescence enhancement and blue shift of DPPL2 upon Zn2+ binding. This phenomenon was a typical photoinduced electron transfer (PET) and intramolecular charge transfer (ICT) process which was attributed to diminishing the electron of the nitrogen lone pair delocalization on the DPP core upon Zn2+ binding. For comparison, DPPL3 (acylation of nitrogen atom of DPPL2) was synthesized and no fluorescence enhancement was observed, which further indicated that lone pair electrons of nitrogen atoms attached to DPP core were ascribed to PET process. 1H NMR titrations and DFT calculations also proved that PET and ICT process of system.
Palladium-catalyzed arylation of linear and cyclic polyamines
Beletskaya, Irina P.,Bessmertnykh, Alla G.,Averin, Alexei D.,Denat, Franck,Guilard, Roger
, p. 261 - 280 (2007/10/03)
The palladium-catalyzed arylation of polyandries is investigated and it is shown that the C-N coupling reaction for a given substrate is strongly dependent on the nature and the concentration of the catalytic system, as well as the nature of the base employed. The arylation of the primary amino group is favored when both primary and secondary amines are present; selective arylation is then possible without using any protecting group. The reaction of dihalobenzenes with polyamines gives the monoamination products in good yields without any significant formation of diamino compounds or reduced derivatives, unlike what is observed when monoamines are used. The extent of polyarylation of polyamines as a function of the excess of aryl halide and the nature and the amount of catalyst is also studied. Finally, N-arylation of a macrocyclic tetraamine (cyclam) is performed by using an appropriate catalytic system. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Halo-substituted aminobenzenes prepared by Pd-catalyzed amination
Beletskaya, Irina P.,Bessmertnykh, Alla G.,Guilard, Roger
, p. 1459 - 1461 (2007/10/03)
The selective monoamination of aryl dihalides by primary amines and polyamines in the presence of the Pd2(dba)3/dppf catalytic system and NaOt- Bu provides a convenient method for the synthesis of aminobenzenes substituted at the ortho, meta, or para position of the aryl ring by a halogen atom. Under these conditions the reaction of polyamine compounds having 1,2-diaminoethane or 1,3-diaminopropane moieties proceeds selectively leading to monoaryl-substituted derivatives of polyamines. Moreover, this is a remarkably efficient method to realize the arylation of a primary amine group of polyamines in the presence of a secondary one.
