73776-25-7Relevant articles and documents
Cytotoxic triterpenoid–safirinium conjugates target the endoplasmic reticulum
Kraft, Oliver,Kozubek, Marie,Hoenke, Sophie,Serbian, Immo,Major, Daniel,Csuk, René
, (2020/10/15)
Safirinium P and Q fluorescence labels were synthesized and conjugated with spacered triterpenoic acids to access hybrid structures. While the parent safirinium compounds were not cytotoxic at all, many triterpenoid safirinium P and Q conjugates showed moderate cytotoxicity. An exception, however, was safirinium P derived compound 30 holding low EC50 = 5.4 μM (for A375 cells) to EC50 = 7.5 μM (for FaDu cells) as well as EC50 = 6.6 μM for non-malignant fibroblasts NIH 3T3. Fluorescence imaging showed that the safirinium core structures cannot enter the cells (not even after a prolonged incubation time of 24 h), while the conjugates (as exemplified for 30) are accumulating in the endoplasmic reticulum but not in the mitochondria. The development of safirinium–hybrids targeting the endoplasmic reticulum can be regarded as a promising strategy in the development of cytotoxic agents.
Synthesis and Antibacterial, Antioxidant, and Molecular Docking Analysis of Some Novel Quinoline Derivatives
Belay, Zerihun,Eswaramoorthy, Rajalakshmanan,Melaku, Yadessa,Zeleke, Digafie
, (2020/08/17)
2-Chloroquinoline-3-carbaldehyde and 2-chloro-8-methylquinoline-3-carbaldehyde derivatives were synthesized through Vilsmeier formulation of acetanilide and N-(o-tolyl)acetamide. Aromatic nucleophilic substitution reaction was used to introduce various nucleophiles in place of chlorine under different reaction conditions. The carbaldehyde group was oxidized by permanganate method and reduced with metallic sodium in methanol and ethanol. The synthesized compounds were characterized by UV-Vis, IR, and NMR. The antibacterial activity of the synthesized compounds was screened against two Gram-positive bacteria (Bacillus subtilis ATCC6633 and Staphylococcus aureus ATCC25923) and two Gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853). Most of the compounds displayed potent activity against two or more bacterial strains. Among them, compounds 6 and 15 showed maximum activity against Pseudomonas aeruginosa with mean inhibition zones of 9.67 ± 1.11 and 10.00 ± 0.44 mm, respectively, while ciprofloxacin showed mean inhibition zone of 8.33 ± 0.44 mm at similar concentration. On the other hand, compound 8 exhibited maximum activity against Escherichia coli with inhibition zones of about 9.00 ± 0.55 mm at 300 μg/mL and 11.33 ± 1.11 mm at 500 μg/mL. The radical scavenging activity of these compounds was evaluated using 1,1-diphenyl-2-picryl hydrazyl (DPPH), and all of them displayed moderate antioxidant activity, with compound 7 exhibiting the strongest activity. The molecular docking study of the synthesized compounds was conducted to investigate their binding pattern with DNA gyrase, all of them were found to have minimum binding energy ranging from -6.0 to -7.33 kcal/mol, and the best result was achieved with compound 11. The findings of the in vitro antibacterial and molecular docking analysis demonstrated that the synthesized compounds have potential of antibacterial activity and can be further optimized to serve as lead compounds.
Synthesis and Bioactivity of Quinoline-3-carboxamide Derivatives
Govender, Hogantharanni,Mocktar, Chunderika,Koorbanally, Neil A.
, p. 1002 - 1009 (2018/02/15)
Twelve novel substituted 2-chloroquinoline-3-carboxamide derivatives were prepared from acetanilides using the Vilsmeier–Haack reaction, producing 2-chloro-3-carbaldehyde quinolines, followed by oxidation of the 3-carbaldehyde to the carboxylic acid and coupling this group with various anilines. The structures of the synthesized compounds were confirmed by NMR, mass spectrometry, and single crystal X-ray diffraction. The chemical shifts of H-5 and H-8 were shown to be influenced by the substituent at C-6. The substituent at C-6 was also seen to affect the chemical shift of C-5, C-7, and C-8, with C-5 and C-7 being more shielded in 5j (F substituted) in comparison with 5g (Cl substituted) and 5d (CH3 substituted). The compounds showed weak activity in the mM range against Gram-positive and Gram-negative bacteria of which 5b, 5d, and 5f showed the best activity with minimum bactericidal concentration values for 5b being 3.79?mM against methicillin-resistant Staphylococcus aureus and 5d and 5f having minimum bactericidal concentration values of 3.77 and 1.79?mM against S.?aureus ATCC 25923, respectively.
TBHP-promoted oxidative cyclization of o-alkynylquinoline aldehydes: Metal/additive-free domino synthesis of pyrano[4,3-b]quinolin-1-ones
Singh, Jay Bahadur,Mishra, Kalpana,Gupta, Tanu,Singh, Radhey M.
supporting information, p. 1019 - 1022 (2018/02/23)
TBHP-promoted domino synthesis of pyrano[4,3-b]quinolin-1-ones is described from o-alkynylquinoline aldehydes. The radical reaction proceeded without metal and additive via oxidation of aldehydic C-H bond into C-OH bond followed by intramolecular 6-endo-d
Friedel-Crafts Chemistry. Part 48. Concise Synthesis of Condensed Azaheterocyclic [1,8]naphthyridinones, Azepino-, Azocino-, and Azoninoquinoline Systems via Friedel-Crafts Ring Closures
Abd El-Aal, Hassan A. K.
, p. 1082 - 1092 (2017/10/10)
Unprecedented construction of a novel series of quinoline heteropolycycles (tetracyclic keto-analogues of [1,8]naphthyridinones, azepino-, azocino-A nd azonino[2,3-b]quinolinones systems) 10a-i by Friedel-Crafts cycliacylation reactions is described. Starting heterocyclic acids precursors 3a-i were prepared from easily accessible 2-chloroquinoline-3-carbaldehyde 1 via a three different synthetic pathways. Acid-catalyzed ring closures of the resulting tosylated acids were achieved under the influence of both Br?nsted and Lewis acid catalysts. The present strategy enables a straightforward synthesis to fused tetracyclic quinolinone skeletons as demonstrated by concise and atom-economical syntheses.
New potential antimalarial agents: Design, synthesis and biological evaluation of some novel quinoline derivatives as antimalarial agents
Radini, Ibrahim Ali M.,Elsheikh, Tarek M. Y.,El-Telbani, Emad M.,Khidre, Rizk E.
, (2016/07/28)
A novel series of dihydropyrimidines (DHPMs) 4a-j; 2-oxopyran-3-carboxylate 7a,b; 1-amino-1,2-dihydropyridine-3-carboxylate 8; and 1,3,4-oxadiazole derivatives 12 with quinolinyl residues have been synthesized in fairly good yields. The structure of the newly synthesized compounds was elucidated on the basis of analytical and spectral analyses. In vitro antimalarial evaluation of the synthesized quinoline derivatives against Plasmodium falciparum revealed them to possess moderate to high antimalarial activities, with IC50 values ranging from 0.014-5.87 μg/mL. Compounds 4b,g,i and 12 showed excellent antimalarial activity against to Plasmodium falciparum compared with the antimalarial agent chloroquine (CQ).
Novel quinoline-imidazolium adducts via the reaction of 2-oxoquinoline-3-carbaldehyde and quinoline-3-carbaldehydes with 1-butyl-3-methylimidazolium chloride [BMIM][Cl]
Laali, Kenneth K.,Insuasty, Daniel,Abonia, Rodrigo,Insuasty, Braulio,Bunge, Scott D.
, p. 4395 - 4399 (2014/07/22)
A library of hydroxyquinolin-3-ylmethylimidazolium adducts were prepared in high yields from the reaction of [BMIM][Cl] with various substituted quinoline-3-carbaldehydes and 2-oxoquinoline-3-carbaldehydes under mild conditions by using sodium acetate in MeCN under ultrasound irradiation. The use of sodium acetate and imidazolium chloride was crucial for the success of these CC bond forming reactions. Attempted coupling with thiazolium bromide led instead to quinoline-3-carboxylic acid.
Synthesis, antitumor activity, and mechanism of action of benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one analogs of acronycine
Tian, Wen,Yougnia, Rodrigue,Depauw, Sabine,Lansiaux, Amélie,David-Cordonnier, Marie-Hélène,Pfeiffer, Bruno,Kraus-Berthier, Laurence,Léonce, Stéphane,Pierré, Alain,Dufat, Hanh,Michel, Sylvie
, p. 10329 - 10342 (2015/02/19)
A series of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one (4), 13-aza derivatives of benzo[b]acronycine, the isomeric 5-methoxy-2,2,13-trimethyl-2,13-dihydro-6H-benzo[b]chromeno[7,6-g][1,8]naphthyridin-6-one (5)
Efficient synthesis and X-ray structures of new α-quinolin-3-yl- α-aminonitriles and derivatives
Ladraa, Souheila,Berrée, Fabienne,Bouraiou, Abdelmalek,Bouacida, Sofiane,Roisnel, Thierry,Carboni, Bertrand,Belfaitah, Ali
, p. 749 - 752 (2013/02/25)
This study describes the synthesis of novel α-aminonitrile derivatives possessing a quinoline subunit via a Strecker reaction. Chiral α-methylbenzylamines were used to carry out the diastereoselective version of this sequence. Conversion of an enantiopure 2-chloroquinolin-3-yl derivative into the corresponding α-aminoester resulted in the concomitant formation of a 2(1H)-quinolinone moiety and a partial racemization. Single crystal X-ray structures are reported for three compounds.
A comparative study of different metal acetylacetonates covalently anchored onto amine functionalized silica: A study of the oxidation of aldehydes and alcohols to corresponding acids in water
Sodhi, Ravinderpal Kour,Paul, Satya,Clark
, p. 1649 - 1656 (2013/02/22)
A series of metal acetylacetonates covalently anchored onto amine functionalized silica were prepared by the complexation of metal acetylacetonates [Co(acac)2, Cu(acac)2, Pd(acac) 2, Ru(acac)3, Mn(acac)3, Co(acac)3] with organically modified 3-aminopropyl silica and their catalytic activities were tested for the oxidation of aromatic aldehydes, α,β-unsaturated aldehydes and benzyl alcohols to the corresponding carboxylic acids in aqueous medium. Different metal acetylacetonates have been chosen with a view to select the most active heterogeneous catalyst for oxidations. The characterization of the catalysts was done on the basis of FTIR, TGA and AAS analysis. SiO 2-Co(acac)2 catalyzes the oxidation of aromatic aldehydes under air atmosphere without using any additional oxidant; however, t-BuOOH was found to be a highly efficient oxidant for the oxidation of α,β- unsaturated aldehydes and heterocyclic aldehydes, as well as the direct oxidation of benzyl alcohols to the corresponding carboxylic acids. The most active catalyst was found to be highly stable and recyclable under the reaction conditions. The Royal Society of Chemistry.
