Docking studies and development of novel 5-heteroarylamino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as potential antimalarials

Joshi, Advait A.; Viswanathan, C. L.

doi:10.1016/j.bmcl.2006.02.038

Cited by 87 publications

(27 citation statements)

References 3 publications

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“…According to a reported procedure, 21a an excess of 2a is necessary to obtain the best result (entry 1); however, the quantity of boronic acid could be reduced with still-acceptable results (entry [3][4][5]. The use of a 2:1 Rh/dppf ratio seems preferable to a 1:1 ratio (entries 1, 2).…”

Section: Methodsmentioning

confidence: 93%

Rh-Catalyzed Sequential Hydroarylation/Hydrovinylation-Heterocyclization of β-(2-Aminophenyl)-α,β-ynones with Organoboron Derivatives: A New Approach to Functionalized Quinolines

Abbiati¹,

Arcadi²,

Marinelli³

et al. 2006

Synlett

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4-Aryl and 4-vinyl quinolines were prepared via a sequential procedure involving regioselective Rh(acac)(C 2 H 2 )/dppfcatalyzed hydroarylation/hydrovinylation of b-(2-aminophenyl)-a,b-ynones with arylboronic acids or potassium aryl and vinyl trifluoroborates, followed by nucleophilic attack of the amino group onto the carbonyl.The quinoline scaffold is found in a variety of biologically active compounds, and quinoline-containing drugs are widely used in treatment of Plasmodium falciparum malaria. 1 Pharmacological studies on new quinoline derivatives appears frequently in current literature dealing with HIV-1 replication inhibition, 2 antimicrobial activity, 3 antihelmintic properties, 4 antimalarial activity 5 and inhibition of VEGF receptors; 6 in particular, 4-arylquinolines have been evaluated for their activity against West Nile Virus, 7 and have found application as ligands of peripheral benzodiazepine receptor. 8 Moreover, conjugated polymers incorporating a 2,4-diarylquinoline subunit are useful chemosensors for fluoride ion, 9 and 1,8-di(4-quinolyl)naphtalene derivatives are selective fluorescent sensors for metal ions in aqueous solution. 10 Consequently, there is a great current synthetic interest in assembling quinoline ring system from acyclic precursors. 11As a part of our ongoing efforts 12 to discover new routes to heterocycles starting from functionalized alkynes bearing proximate nucleophilic centers, we focused on b-(2-aminophenyl)-a,b-ynones 1 as useful building blocks for the synthesis of quinolines through sequential processes involving conjugate-addition-type 13 or cycloaddition 14 reactions followed by cyclization through nucleophilic attack of the amino group onto the carbonyl (cycloamination). In this context, we showed that the reaction of 1 with NaI in acetic acid affords 4-iodoquinolines 3. The potential of 3 as precursors for increasing molecular complexity via palladium-catalyzed reactions has been considered; 13 therefore, the combined addition of NaI to 1/palladiumcatalyzed Suzuki-Miyaura cross-coupling reaction 15 could represent a general entry into 4-aryl and 4-vinylquinolines. Indeed, the reaction of 1a with NaI in acetic acid gave the 4-iodoquinoline 3a (Scheme 1, a); subsequent cross-coupling with phenylboronic acid at room temperature 16 resulted in the formation of 4aa in good yield (Scheme 1, b). Scheme 1Nevertheless, the one-pot synthesis of 4-aryl and 4-vinylquinolines 4 starting from 1 represents a more interesting challenge. 17 In order to achieve this goal , we investigated the development of a one-pot/two-step synthetic protocol. NaI (2 equiv) was added to 1a in ethanol at 80°C in the presence of 1 equivalent of TsOH; after the complete conversion of 1a to 3a (3 h), PhB(OH) 2 (1.3 equiv), K 3 PO 4 (3 equiv), Pd(OAc) 2 (0.03 equiv) and TBAB (0.08 equiv) were added to the reaction mixture allowing the formation of 4a in 47% overall yield after 6 hours at 80°C (Scheme 1, c). Probably there is room for optimization; however, the main drawback of this procedure is const...

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Section: Methodsmentioning

confidence: 93%

Rh-Catalyzed Sequential Hydroarylation/Hydrovinylation-Heterocyclization of β-(2-Aminophenyl)-α,β-ynones with Organoboron Derivatives: A New Approach to Functionalized Quinolines

Abbiati¹,

Arcadi²,

Marinelli³

et al. 2006

Synlett

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“…This pathway was also used for the generation of tri-substituted imidazoles containing benzene rings. However, the yields were found to be much lower than those achieved for tri-substituted imidazoles bearing furan rings [161]. Several 1,2-di(furan-2-yl)-2-oxoethyl carboxylates were easily prepared by the esterification of furan (1,2-di(furan-2-yl)-2-hydroxyethanone generated from furfural [162] using acyl chlorides, and pyridine as catalyst in high yields under mild reaction conditions.…”

Section: Synthesis Of 245-tri-aryl-1h-imidazolesmentioning

confidence: 97%

“…These properties may be responsible for the small number of reports in the literature regarding the synthesis of imidazoles bearing furan ring as a substituent [161]. While the biological and pharmacological potency of tetra-substituted imidazoles have been extensively investigated, their luminescence properties have been largely overlooked, except for 1-R 1 -2-R-4,5-dialkyl-1H -imidazoles [204].…”

Section: Synthesis Of 1245-tetra-aryl-1h-imidazolesmentioning

confidence: 98%

Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles

2015

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“…Imidazole derivatives play an important role in biochemistry (Bräse et al, 2002;Nicolaou et al, 2002;Chen et al, 2005;Costantino & Barlocco, 2006;Joshi & Viswanathan, 2006) as materials including luminescent Fang et al, 2007) and proton conductive materials (Schuster et al, 2004;Benhabbour et al, 2005), medicinal chemicals (Nefzi et al, 1997;Frazén, 2000;Horton et al, 2003;Fantini et al, 2010;Soh & Lam, 2010) and in the determination of heavy metal ions Kang et al, 2011;Li et al, 2012) as they possess better pharmacological and luminescent properties. Recently, compounds with furan-rings have been reported for the determination of trace amounts of Cu 2+ with a limit of detection (3σ) of 6.5 × 10 −11 mol L −1 , which has prompted us to explore the synthesis and luminescence property of imidazoles bearing furan rings.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles

Zhang

Chen

et al. 2015

Chemical Papers

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A solvent-free microwave-assisted method for the synthesis of 2-substituted-4,5-di(2-furyl)-1H-imidazoles was developed. Imidazoles with moderate to good yields were produced by condensation of furil with aldehydes over acidic alumina impregnated with ammonium acetate, and they were characterized by FT-IR, HRMS, 1 H NMR and 13 C NMR spectroscopy. Crystal structure of 2,4,5-tri-2-furyl-1H-imidazole (I ) in the orthorhombic space group Pbca was reported, which showed more coplanarity than the reported crystal structure of I in the monoclinic space group Cc. Moreover, their luminescent properties were investigated. It was found that the organic small molecule compounds synthesized possess higher fluorescence quantum efficiency (up to 0.508) in a 0.1 M H2SO4 aqueous solution dissolved in 0.5 mL of CH3OH; along with higher stability; also the emission of some compounds synthesized in the solution was sensitive to the polarity of the solvents.

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Docking studies and development of novel 5-heteroarylamino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as potential antimalarials

Cited by 87 publications

References 3 publications

Rh-Catalyzed Sequential Hydroarylation/Hydrovinylation-Heterocyclization of β-(2-Aminophenyl)-α,β-ynones with Organoboron Derivatives: A New Approach to Functionalized Quinolines

Rh-Catalyzed Sequential Hydroarylation/Hydrovinylation-Heterocyclization of β-(2-Aminophenyl)-α,β-ynones with Organoboron Derivatives: A New Approach to Functionalized Quinolines

Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles

Microwave-assisted solvent-free synthesis and luminescence properties of 2-substituted-4,5-di(2-furyl)-1H-imidazoles

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