333408-31-4Relevant academic research and scientific papers
Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition
Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Shaikh, Saba Kauser J.,Hoolageri, Swati R.,Kodasi, Barnabas,Joshi, Shrinivas D.,Kumbar, Vijay M.
, (2021/04/12)
Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones 8j-v were synthesized by click chemistry as an ultimate tactic where [3 + 2] cycloaddition of azides with terminal alkynes has been evolved. Herein, we are inclined to divulge the implication and prevalence of CuSO4·5H2O and THF/water promoted [3 + 2] cycloaddition reactions. The foremost supremacy of this method are transitory reaction times, facile workup, excellent yields (88–92%) with exorbitant purity and regioselective single product formation both under conventional and microwave method. Docking studies illustrated strong binding interactions with enzyme InhA-D148G (PDB ID: 4DQU) by means of high C-score values. The anti-tubercular and antifungal screening of synthesized compounds proclaimed promising activity. The in vitro and in silico studies imply that these triazoles appended quinolines may acquire the ideal structural prerequisites for auxiliary expansion of novel therapeutic agents.
Microwave assisted synthesis of quinoline fused benzodiazepines as anxiolytic and antimicrobial agents
Marganakop,Kamble,Nesaragi,Bayannavar,Joshi,Kattimani,Sudha
, p. 1107 - 1114 (2021/05/10)
In the present study, an efficient, facile and green protocol for synthesis of quinoline fused 1,4-benzodiazepine (4a-j) by microwave irradiated condensation of 6/7/8-substituted 3-bromomethyl-2-chloro-quinoline (3a-j) obtained from 2-chloro 6/7/8-substituted quinoline-3-carbaldehyde (1a-j) with 1, 2-phenylenediamine was developed. Surflex docking studies with K+ channel is one of the physiological targets and inhibition, which plays a role in the pathophysiology of depression revealed that all these compounds show consensus score in the range 2.71-3.68 indicating the summary of all forces of interaction. Further, compounds 4d, 4g and 4i exhibited potent antibacterial activity.
Chemoselective transfer hydrogenation of aromatic and heterocyclic aldehydes by green chemically prepared cobalt oxide nanoparticles
Krishnaveni,Lakshmi,Kaveri,Kadirvelu
, (2020/09/16)
A new surfactant (quercetin) assisted hydrothermal method is used for the preparation of phase pure cobalt oxide (Co3O4) nanoparticles (Nps). The quercetin acted well as surfactant in producing size controlled Nps. The produced Nps were extensively characterized by various techniques to reveal its chemical composition, structure, morphology, size and thermal behavior. The main objective of the study is to employ the prepared material as heterogeneous catalyst for hydrogenation of therapeutically important aldehydes. The capability of the catalyst is appear to be good, since the yield of alcohols from structurally different aldehydes is adequate with short period of time. Also the catalyst is recyclable, stable, no need of addition of ligands for activation and environmentally benign.
Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies
Shaikh, Saba Kauser J.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Somagond, Shilpa M.,Joshi, Shrinivas D.
, (2019/12/11)
The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a–m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and pharmacokinetic evaluation.
Facile Synthesis of 2-Acylthieno[2,3- b]quinolines via Cu-TEMPO-Catalyzed Dehydrogenation, sp2-C-H Functionalization (Nucleophilic Thiolation by S8) of 2-Haloquinolinyl Ketones
Nawaz Khan, Fazlur Rahman,Teja, Chitrala
supporting information, p. 1726 - 1730 (2020/03/24)
An efficient, solvent-free synthesis of 2-acylthieno[2,3-b]quinolines is reported from 2-halo-quinolinyl ketones through Cu-TEMPO catalyzed dehydrogenation, sp2-C-H functionalization using elemental sulfur as thiol surrogate (sulfur source) and tetrabutylammonium acetate as an ionic reaction medium. The optimized reaction conditions give excellent product yields under mild reaction conditions with chemoselectivity and broad functional group tolerance. The synthetic importance of the synthesized molecules is showcased further by Friedl?nder annulation, reduction, and alkene functionalization reactions.
Methanol as hydrogen source: Transfer hydrogenation of aromatic aldehydes with a rhodacycle
Aboo, Ahmed H.,Bennett, Elliot L.,Deeprose, Mark,Robertson, Craig M.,Iggo, Jonathan A.,Xiao, Jianliang
supporting information, p. 11805 - 11808 (2018/11/10)
A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.
INHIBITORS OF PI3K-DELTA AND METHODS OF THEIR USE AND MANUFACTURE
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Page/Page column 72; 73, (2012/04/04)
The invention is directed to Compounds of Formula I: and pharmaceutically acceptable salts or solvates thereof, as well as methods of making and using the compounds
Synthetic Route for New (Z)-5-[4-(2-Chloroquinolin-3-yl) Methoxy]benzylidinethiazolidine-2,4-diones
Jawale, Dhanaji V.,Pratap, Umesh R.,Mane, Ramrao A.
experimental part, p. 2171 - 2177 (2012/06/01)
Synthetic route has been developed for the synthesis of new (Z)-5-[4-(2-chloroquinolin-3-yl) methoxy]benzylidinethiazolidine-2,4-diones (6a-h) starting from 2-chloro-3-hydroxymethyl quinolines (2a-h). The hydroxy methyl quinolines on tosylation yielded (3a-h). Condensation of the tosyl intermediates with 4-hydroxy benzaldehydes has been carried in DMF in presence of K2CO3 and obtained 4-quinolinyl methoxy benzaldehydes (4a-h). Conveniently Knoevenagel condensation of quinolinyl methoxy benzaldehydes (4a-h) and 2, 4-thiazolidinedione (5) has been carried in PEG-400 in presence of L-proline and obtained better yields of the titled compounds (6a-h).
Synthesis of New dihydropyrimidinones catalysed by dicationic ionic Liquid
Jawale, Dhanaji V.,Pratap, Umesh R.,Mulay, Aparna A.,Mali, Jyotirling R.,Mane, Ramrao A.
experimental part, p. 645 - 655 (2012/07/03)
A convenient multi step synthetic protocol for new dihydropyrimidinones bearing quinolynyl methoxy phenyl moiety has been developed from 2-chloro-3-formyl quinolines. The last step is one-pot Biginelli reaction of multicomponents, 4-((2-chloroquinolin-3-yl) methoxy) benzaldehydes, ethyl acetoacetate and urea mediated and catalysed by dicationic ionic liquid (3-methyl-1-[3-(methyl-1H-imidazolium-1-yl) propyl]- 1H-imidazolium dibromide (C3 [min]2 2 [Br-] )). Simple work-up procedures and moderate to good yields of the pyrimidinones and the intermediates are the merits of the route. Indian Academy of Sciences.
Synthesis, antidepressant and antifungal evaluation of novel 2-chloro-8-methylquinoline amine derivatives
Kumar, Suresh,Bawa, Sandhya,Drabu, Sushma,Gupta, Himanshu,MacHwal, Lalit,Kumar, Rajiv
experimental part, p. 670 - 675 (2011/03/19)
A new series of N-[(2-chloro-8-methylquinolin-3-yl)methyl]-(substituted)- aniline/butylamine/cyclohexylamine/benzylamine derivatives (4a-p) was synthesized by nucleophilic substitution reaction of 2-chloro-3-(chloromethyl)- 8-methylquinoline 3 with various aliphatic and aromatic amines in absolute ethanol in the presence of triethylamine (TEA). The newly synthesized secondary amines were characterized by the combined use of IR, 1H NMR, 13C NMR, mass spectral data and microanalyses. The antidepressant activity of the synthesized compounds (4a-p) was evaluated by Forced swim test in rats and their neurotoxicity was evaluated by the rotarod test. Test compounds and clomipramine were administered intraperitoneally at dose of 100 mg/kg and 20 mg/kg respectively. Preliminary antidepressant screening of compounds (4a-p) revealed that compounds 4b, 4c, 4d, 4e, 4i and 4o significantly (P 0.01) reduces the duration of immobility time. These compounds were also tested in-vitro for MAO inhibitory effect. All the compounds were also screened for antifungal activity against Aspergillus niger MTCC 281, Aspergillus flavus MTCC 277, Monascus purpureus MTCC 369 and Penicillium citrinum NCIM 768 strains.
