23851-84-5Relevant articles and documents
Click chemistry approach: Regioselective one-pot synthesis of some new 8-trifluoromethylquinoline based 1,2,3-triazoles as potent antimicrobial agents
Garudachari,Isloor, Arun M.,Satyanarayana,Fun, Hoong-Kun,Hegde, Gurumurthy
, p. 324 - 332 (2014/02/14)
Three series of 8-trifluoromethylquinoline based 1,2,3-triazoles derivatives (5a-c, 6a-d and 7a-c) were synthesized by multi-step reactions by click chemistry approach. Synthesized compounds were characterized by spectral studies and X-ray analysis. The final compounds were screened for their in-vitro antimicrobial activity by well plate method (zone of inhibition). Compounds 5c, 6b, 8b, 11 and 12 were found to be active against tested microbial strains. The results are summarized in Tables 5 and 6.
How to convert a walk-in hood into a manufacturing facility: Demonstration of a continuous, high-temperature cyclization to process solids in flow
White, Timothy D.,Alt, Charles A.,Cole, Kevin P.,Groh, Jennifer McClary,Johnson, Martin D.,Miller, Richard D.
, p. 1482 - 1491 (2015/02/19)
An intramolecular thermal cyclization protocol was developed in a flow reactor to take advantage of the high pressures and temperatures that are easily obtained in small scale autoclave reactors that have been modified to handle slurries. This reactor was equipped with a fill/empty pumping system to enable easy and nearly complete transfer of slurries. The reaction conditions were designed to take advantage of the insolubility of the product in order to separate it from residual starting material by filtration after short reaction times. Recycling of the filtrate maximized the yield and throughput while minimizing decomposition. Recycles were accomplished using a strip to dryness protocol that was easily performed in a rotary evaporator. This new equipment set was designed with lab-hood manufacturing in mind, a minimized footprint, and the system was completely automated for charging, emptying, rinsing, and reacting. Additional efforts for quick screening and alternate modes of addition were also investigated.
Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents
Garudachari,Isloor, Arun M.,Satyanarayana,Fun, Hoong-Kun,Pavithra,Kulal, Ananda
, p. 422 - 432 (2013/10/01)
Three series of new trifluoromethyl substituted quinolone derivatives were synthesized (4a-f, 6a-f and 8a-f) from corresponding substituted anilines by multi-step reactions. The regioselective alkylation with different alkyl halides were carried out by approaching two different routes to get the final products in good yield. Newly synthesized compounds were characterized by spectral study and also by C, H, N analyses. Three dimensional structure of 2b and 4b were also confirmed by single crystal X-ray studies. The final compounds (4a-f, 6a-f and 8a-f) were screened for their in-vitro antibacterial and antifungal activity by well plate method (zone of inhibition). The results revealed that, compounds 4a, 6b, 6c and 8e showed significant antibacterial activity as compared to the standard drug Ciprofloxacin. The compound 8a was found to be a potent antifungal agent.
Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents
Thomas,Adhikari, Airody Vasudeva,Telkar, Sandeep,Chowdhury, Imran H.,Mahmood, Riaz,Pal, Nishith K.,Row, Guru,Sumesh
, p. 5283 - 5292 (2011/12/14)
Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized title compounds were evaluated for their antimicrobial activities including antimycobacterial activity. Amongst the tested compounds, 5b, 5e, 5h, 5j, 6c and 7c displayed promising antimicrobial activity. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands, 5b, 5e, 5h, 5j and 6c.
Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents
Eswaran, Sumesh,Adhikari, Airody Vasudeva,Pal, Nishith K.,Chowdhury, Imran H.
supporting information; experimental part, p. 1040 - 1044 (2010/06/14)
A series of 26 new quinoline derivatives carrying active pharmacophores has been synthesized and evaluated for their in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv (MTB), Mycobacterium smegmatis (MC2), and Mycobacterium fortuitum following the broth micro dilution assay method. Compounds 13e, 13i, 13k, 14a, 14c, 14i, and 14k exhibited significant minimum inhibition concentrations, when compared with first line drugs isoniazid (INH) and rifampicin (RIF) and could be ideally suited for further modifications to obtain more efficacious compounds in the fight against multi-drug resistant tuberculosis.
Quinoline-3-carboxamide containing sulfones as liver X receptor (LXR) agonists with binding selectivity for LXRβ and low blood-brain penetration
Hu, Baihua,Bernotas, Ron,Unwalla, Rayomand,Collini, Michael,Quinet, Elaine,Feingold, Irene,Goos-Nilsson, Annika,Wilhelmsson, Anna,Nambi, Ponnal,Evans, Mark,Wrobel, Jay
scheme or table, p. 689 - 693 (2010/06/14)
A series of quinoline-3-carboxamide containing sulfones was prepared and found to have good binding affinity for LXRβ and moderate binding selectivity over LXRα. The 8-Cl quinoline analog 33 with a high TPSA score, displayed 34-fold binding selectivity for LXRβ over LXRα (LXRβ IC50 = 16 nM), good activity for inducing ABCA1 gene expression in a THP macrophage cell line, desired weak potency in the LXRα Gal4 functional assay, and low blood-brain barrier penetration in rat.
Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety
Eswaran, Sumesh,Adhikari, Airody Vasudeva,Shetty, N. Suchetha
experimental part, p. 4637 - 4647 (2009/12/26)
A new class of quinoline derivatives containing 1,2,4-triazole moiety were synthesized from derivatives of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide 4 through multi-step reactions. The compound 4, on treatment with substituted Isothiocyanates yielded quinoline-thiosemicarbazides 5a-c, which were conveniently cyclized to (5-mercapto-4H-triazol-3-yl)-quinolin-4-ols 6a-c in basic medium. These intermediates were then transformed to their respective chloro derivatives 7a-c by treatment with phosphorus oxychloride, which on further reaction with different biologically active rare amines yielded the target compounds 8a-g, 9a-h and 10a-h in good yield. The ultimate step, involving nucleophilic substitution reaction was achieved by microwave-induced technique, which has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that most of the compounds demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 μg/mL.
Quinolines useful in treating cardiovascular disease
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Page/Page column 28, (2008/06/13)
This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.
Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors
Zask,Gu,Albright,Du,Hogan,Levin,Chen,Killar,Sung,DiJoseph,Sharr,Roth,Skala,Jin,Cowling,Mohler,Barone,Black,March,Skotnicki
, p. 1487 - 1490 (2007/10/03)
Potent and selective bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors were synthesized by a novel convergent route. Selectivity and efficacy versus MMPs and TACE could be controlled by appropriate substitution on the scaffolds and by variation of the P1′ group. Select compounds were found to be effective in in vivo models of arthritis.
