333408-48-3Relevant 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.
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.
Synthesis of New dihydropyrimidinones catalysed by dicationic ionic Liquid
Jawale, Dhanaji V.,Pratap, Umesh R.,Mulay, Aparna A.,Mali, Jyotirling R.,Mane, Ramrao A.
, 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.
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).
Simple and efficient synthesis of new O,O-diethyl phosphorothioates
Pokalwar,Hangarge,Kategaonkar,Shingare
experimental part, p. 430 - 433 (2009/09/06)
A simple and highly effective method was developed for the synthesis of new O,O-diethyl phosphorothioates from O,O-diethyl phosphorochloridothioate and 2-chloroquinolin-3-ylmethanol derivatives in the presence of sodium hydroxide.
