- Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents
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Several classes of antimalarial drugs are currently available, although issues of toxicity and the emergence of drug resistant malaria parasites have reduced their overall therapeutic efficiency. Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated for in vitro antiplasmodial activity against the 3D7 chloroquine-sensitive strain of Plasmodium falciparum, and compounds 40 and 59 emerged as the most promising with IC50 values of 0.23 and 0.93 μM, respectively. The most promising compounds were also evaluated in silico by molecular docking protocols for binding affinity to the {0 0 1} fast-growing face of a hemozoin crystal model.
- Bokosi, Fostino R.B.,Beteck, Richard M.,Mbaba, Mziyanda,Mtshare, Thanduxolo E.,Laming, Dustin,Hoppe, Heinrich C.,Khanye, Setshaba D.
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- Microwave assisted synthesis of quinoline fused benzodiazepines as anxiolytic and antimicrobial agents
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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.
- Marganakop,Kamble,Nesaragi,Bayannavar,Joshi,Kattimani,Sudha
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p. 1107 - 1114
(2021/05/10)
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- Chemoselective transfer hydrogenation of aromatic and heterocyclic aldehydes by green chemically prepared cobalt oxide nanoparticles
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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.
- Krishnaveni,Lakshmi,Kaveri,Kadirvelu
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- Convenient synthesis of quinoline-fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C-H functionalisation of triazoles
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The efficient and convenient synthesis of a new fused heterocyclic scaffold comprising three different heterocycles, viz., quinolines, azepines/oxepines and triazoles is reported from quinoline-tethered triazoles. The quinoline-tethered triazoles were eas
- Mahesh, Kukkamudi,Ravi, Kanakaraju,Rathod, Praveen Kumar,Leelavathi, Panaganti
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p. 2367 - 2373
(2020/02/20)
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- Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies
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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.
- Shaikh, Saba Kauser J.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Somagond, Shilpa M.,Joshi, Shrinivas D.
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- Methanol as hydrogen source: Transfer hydrogenation of aromatic aldehydes with a rhodacycle
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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.
- Aboo, Ahmed H.,Bennett, Elliot L.,Deeprose, Mark,Robertson, Craig M.,Iggo, Jonathan A.,Xiao, Jianliang
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supporting information
p. 11805 - 11808
(2018/11/10)
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- Tetrazolylmethyl quinolines: Design, docking studies, synthesis, anticancer and antifungal analyses
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A new series of 2,5 and 1,5-regioisomers of the tetrazolyl group viz., 3-[(5-benzyl/benzylthio-2H-tetrazol-2-yl) methyl]-2-chloro-6-substituted quinoline 6h-q and 3-[(5-benzyl/benzylthio-1H-tetrazol-1-yl) methyl]-2-chloro-6-substituted quinolines 7h-q were synthesized. Docking studies of all these compounds with DNA as target using PDB: 1AU5 and 453D revealed that the compounds 6h and 6i act as covalent cross linker on the DNA helix of the former and intercalate the latter both with higher C score values. Another set of docking studies in the active pocket of dihydrofolate reductase and N-myristoyl transferase as targets to assess antifungal activity revealed that compounds 6k, 6l, 6p and 7q (with bromo and fluro substituents) showcases different binding modes and hydrogen bonding. Further, the compounds were screened for anticancer activity (primary cytotoxicity) against NCI-60 Human tumor cell line at a single high dose (10?5M) concentration assay. Among the tested compounds, 6h has shown 99.28% of GI against Melanoma (SK-MEL-5) and compound 6i has shown 97.56% of GI against Breast Cancer (T-47D). Further, in vitro antifungal assay against A. fumigatus and C. albicans for these compounds 6h-q and 7h-q revealed potential to moderate activities as compared to the standard.
- Shaikh, Saba Kauser J.,Kamble, Ravindra R.,Somagond, Shilpa M.,Devarajegowda,Dixit, Sheshagiri R.,Joshi, Shrinivas D.
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p. 258 - 273
(2017/02/15)
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- Design of new hybrid template by linking quinoline, triazole and dihydroquinoline pharmacophoric groups: A greener approach to novel polyazaheterocycles as cytotoxic agents
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A new hybrid template designed by linking three pharmacophoric groups, for example, quinoline, triazole and dihydroquinoline moieties have been used for the generation of a library of molecules as potential cytotoxic agents. Synthesis of these polyazaheterocycles were carried out by using a strategy that involved one-pot sequential azidation and CuAAC in water under mild conditions. A number of 1,4-disubstituted 1,2,3-triazoles possessing quinolinylmethylene at N-1 and 1,2-dihydroquinolinyl methylene at C-4 as different substituents were synthesized and evaluated for their cytotoxic effects against various cancer cells. Some of them showed encouraging activities against lung cancer cells and one of them showed inhibition of PDE4 indicating the potential medicinal value of these novel polyazaheterocycles.
- Praveena, Koduru Sri Shanthi,Shivaji Ramarao, Edupuganti Veera Venkat,Murthy, Nandula Yadagiri Sreenivasa,Akkenapally, Surekha,Ganesh Kumar,Kapavarapu, Ravikumar,Pal, Sarbani
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p. 1063 - 1069
(2015/02/19)
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- Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: Synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities
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A series of quinoline based 1,3,4-oxadiazole derivatives (8a-l) were synthesized by a chloro-amine coupling reaction approach with different catalysts and solvents. Substituted 1,3,4-oxadiazole intermediates 7a-c were obtained from 2-substituted-N-phenylh
- Ladani, Gaurav G.,Patel, Manish P.
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p. 9848 - 9857
(2015/12/01)
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- Synthesis, crystal structure, ABTS radical-scavenging activity, antimicrobial and docking studies of some novel quinoline derivatives
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In this study, a series of nine novel 2-chloroquinolin-3-yl ester derivatives have been synthesized via a two-step protocol from 2-chloroquinoline-3-carbaldehyde. The structures of all these compounds were confirmed by spectral data. The single crystal X-
- Tabassum, Sumaiya,Suresha Kumara,Jasinski, Jerry P.,Millikan, Sean P.,Yathirajan,Sujan Ganapathy,Sowmya,More, Sunil S.,Nagendrappa, Gopalpur,Kaur, Manpreet,Jose, Gilish
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- A remarkably faster approach towards 1,2,3-triazolyl quinolines via CuAAC in water: Their crystal structure analysis and antibacterial activities
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A series of 1,2,3-triazolyl quinolines possessing substituents like -CH2OAr (Ar = aryl) moiety on the triazolyl ring were synthesized via a multi-step sequence consisting of copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 3-(azidomethyl)
- Mareddy, Jyoti,Shanthi Praveena, Koduru Sri,Suresh, Nallapati,Jayashree, Anireddy,Roy, Soma,Rambabu, Dandela,Sreenivasa Murthy, Nandula Yadagiri,Pal, Sarbani
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p. 343 - 352
(2013/07/26)
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- Synthesis of New dihydropyrimidinones catalysed by dicationic ionic Liquid
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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.
- Jawale, Dhanaji V.,Pratap, Umesh R.,Mulay, Aparna A.,Mali, Jyotirling R.,Mane, Ramrao A.
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p. 645 - 655
(2012/07/03)
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- Synthetic Route for New (Z)-5-[4-(2-Chloroquinolin-3-yl) Methoxy]benzylidinethiazolidine-2,4-diones
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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).
- Jawale, Dhanaji V.,Pratap, Umesh R.,Mane, Ramrao A.
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experimental part
p. 2171 - 2177
(2012/06/01)
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- Synthesis and antibacterial evaluation of some novel 1,3,4-oxadiazol derivatives incorporated with quinoline moiety
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5-(3,4,5-Triethoxyphenyl)-1,3,4-oxadiazole-2-thiol 6 on treatment with substituted 3-(bromomethyl)-2-chloroquinoline or 2-(p-tolyloxy)-3-(bromomethyl) quinoline 4a-j afforded the corresponding 3-((5-(3,4,5-triethoxyphenyl)-1,3,4- oxadiazol-2-ylthio)methyl)-2-chloroquinoline or 3-((5-(3,4,5-triethoxyphenyl)-1, 3,4-oxadiazol-2-ylthio)methyl)-2-(p-tolyloxy)quinoline 7a-j, in the presence of K2CO3 and DMF under stirring at ambient temperature. All the synthesized compounds were further screened for their antibacterial activities. Some of our compounds showed excellent antibacterial activities against test organisms and reference standard.
- Mandhane, Priyanka G.,Joshi, Ratnadeep S.,Khan, Wajid,Gill, Charansingh H.
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scheme or table
p. 656 - 661
(2011/10/09)
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- ZnO nanoparticles in the synthesis of AB ring core of camptothecin
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For the first time, synthesis of AB ring core of camptothecin synthons such as (2-chloroquinolin-3-yl)methanols (Va-Vg) using zinc oxide nanoparticles is reported. The desired attractive products were obtained in high yields, short reaction time, using a simple work-up procedure with the purification of products by non-chromatographic methods.
- Roopan, Selvaraj Mohana,Nawaz Khan, Fazlur Rahman
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p. 812 - 817
(2011/11/11)
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- FLUOROBORON COMPOUND HAVING AROMATIC RING OR SALT THEREOF, AND PROCESS FOR PRODUCTION OF COMPOUND HAVING CYCLIC ETHER-FUSED AROMATIC RING BY USING THE SAME
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Provided is a fluoroboron compound which is highly safe and stable and is capable of forming a cyclic ether-fused ring by the intramolecular alkoxymethylation reaction, or a salt thereof. The compound can be synthesized by the intramolecular alkoxymethylation reaction of a fluoroboron compound represented by the formula (I) or a salt thereof in the presence of a metal catalyst. (wherein the moiety represented by the formula represents an aromatic ring; L represents a substituent such as a halogen atom; R represents a substituted or unsubstituted alkylene group having 1 or 2 carbon atoms; and M represents an alkali metal cation or the like, with the proviso that L and -R-OCH2BF3M are respectively located on contiguous carbon atoms on the aromatic ring, or in the case of a fused aromatic ring, on two carbon atoms adjacent to one carbon at the fused position).
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Page/Page column 19
(2009/06/27)
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- Simple and efficient synthesis of new O,O-diethyl phosphorothioates
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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.
- Pokalwar,Hangarge,Kategaonkar,Shingare
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experimental part
p. 430 - 433
(2009/09/06)
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- Bridged 5,6,7,8-tetrahydro-1,6-naphthyridines, analogues of huperzine A: Synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase
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Derivatives of 6,8-bridged 5,6,7,8-tetrahydro-1,6-naphthyrid-ines, designed as analogues of huperzine A, were synthe-sised and evaluated as inhibitors of acetylcholinesterase. In a first approach, C3-bridged naphthyridines were constructed by internal nucleophilic aromatic substitution of 2-chloro-3-(1-piperidinylmethyl)pyridine precursors containing a 3-CO 2Me group on the 1-piperidinyl ring moiety. Alternatively, ring-closing metathesis on 6,8-diallyl-substituted tetrahydro-1,6-naphthyridines was applied to construct an unsaturated C4 bridge. Some of the target compounds showed inhibition of acetylcholinesterase but lower than that of huperzine A. The relative order of inhibition activities could be rationalised by comparative docking simulation studies on the basis of the known crystal structure of the ace-tylcholinesterase-huperzine A complex.
- Vanlaer, Sofie,Voet, Arnout,Gielens, Constant,De Maeyer, Marc,Compernolle, Frans
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experimental part
p. 643 - 654
(2009/07/17)
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- Synthesis of Substituted 8-Amino-2-chloroquinolines
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A convenient synthesis of 3,6,7-trisubstituted 2-chloro-8-nitroquinolines (7-17) is described.The orientation of nitro group in compounds 5-8 has been ascertained by comparing their PMR and 13C NMR data with those of the appropriate precursors
- Bhat, Balkrishen,Bhaduri, A. P.
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