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1.
《Journal of heterocyclic chemistry》2018,55(1):103-114
A series of substituted 1,8‐naphthyridine derivatives was synthesized as cytotoxic agent by using starting material 1,4‐dihydro‐4‐oxo‐1,8‐naphthyridine‐3‐carbohydrazide ( 1 ). Further reactions on compound 1 were processed with different reagents to afford the corresponding 3‐heteraryl‐1,8‐naphthyridine derivatives 2–22 . In vitro cytotoxic activities of new synthesized compounds were assayed against Ehrlich ascites carcinoma, which showed that compounds 3 and 12 had the more potent cytotoxic activity. 相似文献
2.
Ethyl 1‐ethyl‐7‐methyl‐4‐oxo‐1,4‐dihydro[1,8]naphthyridine‐3‐carboxylate ( 1 ), precursor of nalidixic acid, has been converted in two steps through ([1,8]naphthyridin‐3‐yl)carbonylguanidine derivatives into substituted pyrimido[4,5‐b] and [5,4‐c][1,8]naphthyridines. 相似文献
3.
Petra Drevenek Ivan Leban Iztok Turel Gerald Giester Ekkehart Tillmanns 《Acta Crystallographica. Section C, Structural Chemistry》2003,59(9):m376-m378
The X‐ray structure analysis of the title compound, chloro[1‐cyclopropyl‐6‐fluoro‐1,4‐dihydro‐4‐oxo‐7‐(piperazin‐4‐ium‐1‐yl)‐3‐quinolinecarboxylate‐κ2O3,O4](1,10‐phenanthroline‐κ2N,N′)copper chloride dihydrate, [CuCl(C17H18FN3O3)(C12H8N2)]Cl·2H2O or [CuCl(cfH)(phen)]Cl·2H2O, where cfH is 1‐cyclopropyl‐6‐fluoro‐1,4‐dihydro‐4‐oxo‐7‐(piperazin‐4‐ium‐1‐yl)‐3‐quinolinecarboxylate and phen is 1,10‐phenanthroline, shows that the geometry around the Cu ion is a slightly distorted square pyramid. Two O atoms of the carbonyl and carboxyl groups of ciprofloxacin and two N atoms of 1,10‐phenanthroline are coordinated to the metal centre in the equatorial plane, and a Cl− ion is coordinated at the apical position. Extensive intermolecular hydrogen bonding produces a supramolecular structure that consists of alternating six‐ and 12‐membered rings. 相似文献
4.
Ahmed I. Khodair Mona A. Elsafi Siham A. Al‐Issa 《Journal of heterocyclic chemistry》2019,56(9):2358-2368
A series of 3‐substituted 2‐thioxo‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones 4a – e were synthesized from the reaction of 3‐aminonaphthalene‐2‐carboxylic acid 1 with isothiocyanate derivatives 2a – e . The alkylation of 4a – e with alkyl halides gave 3‐substituted 2‐alkylsulfanyl‐2,3‐dihydro‐1H‐benzo[g]quinazolin‐4‐ones 5a – o . S‐Glycosylation was carried out via the reaction of 4a – e with glycopyranosyl bromides 7a and 7b under anhydrous alkaline conditions. The structure of the compounds was established as S‐nucleoside and not N‐nucleoside. Conformational analysis has been studied by homonuclear and heteronuclear two‐dimensional NMR methods (2D DFQ‐COSY, heteronuclear multiple quantum coherence, and heteronuclear multiple bond correlation). The S site of alkylation and glycosylation was determined from the 1H and 13C heteronuclear multiple quantum coherence experiments. 相似文献
5.
The 1‐cyclopropyl‐6‐fluoro‐1,4‐dihydro‐4‐oxo‐7‐(piperazin‐1‐yl)quinoline‐3‐carboxylic acid (=ciprofloxacin; 1 ) undergoes low‐efficiency (Φ=0.07) substitution of the 6‐fluoro by an OH group on irradiation in H2O via the ππ* triplet (detected by flash photolysis, λmax 610 nm, τ 1.5 μs). Decarboxylation is a minor process (≤5%). The addition of sodium sulfite or phosphate changes the course of the reaction under neutral conditions. Reductive defluorination is the main process in the first case, while defluorination is accompanied by degradation of the piperazine moiety in the presence of phosphate. In both cases, the initial step is electron‐transfer quenching of the triplet (kq=2.3⋅108M −1 s−1 and 2.2⋅107M −1 s−1, respectively). Oxoquinoline derivative 1 is much more photostable under acidic conditions, and in this case the F‐atom is conserved, and the piperazine group is stepwise degraded (Φ=0.001). 相似文献
6.
A series of N‐substituted 1,4‐dihydro‐4‐oxo‐1,8‐naphthyridine‐3‐carboxylate esters has been prepared in two steps from ethyl 2‐(2‐chloronicotinoyl)acetate. Treatment of the β‐ketoester with N,N‐dimethylformamide dimethyl acetal in N,N‐dimethylformamide (DMF) gave a 95% yield of the 2‐dimethylaminomethylene derivative. Subsequent reaction of this β‐enaminone with primary amines in DMF at 120oC for 24 h then afforded the target compounds in 47–82% yields by a tandem SNAr‐addition‐elimination reaction. Synthetic and procedural details as well as a mechanistic rationale are presented. 相似文献
7.
F. R. G. Bergamini M. A. Ribeiro P. C. M. L. Miranda A. L. B. Formiga P. P. Corbi 《Acta Crystallographica. Section C, Structural Chemistry》2016,72(7):544-548
The identification of the antibacterial action of nalidixic acid (nx) was central to the development of the quinolone antibacterial compounds. The ability of the nx naphthyridyl ring to interact with and inhibit some proteins has encouraged the investigation of similar structures in the search for more active compounds with less adverse effects. The possibility of structural modification by attachment of other biologically active moieties to the naphthyridyl ring of nx allowed the development of new active antimicrobial molecules. Hydrazone derivatives of nx can be synthesized easily based on the condensation of the hydrazide derivative of nx with the desired aldehyde or ketone. Only a few complexes with nx hydrazone derivatives have been described but for none were the crystal structures elucidated. The synthesis of a new one‐dimensional CuII coordination polymer, namely catena‐poly[[copper(II)‐di‐μ‐chlorido‐copper(II)‐{μ‐1‐ethyl‐N′‐[(1H‐imidazol‐4‐yl)methylidene]‐7‐methyl‐4‐oxo‐1,4‐dihydro‐1,8‐naphthyridine‐3‐carbohydrazidato}‐[dimethanolcopper(II)]‐{μ‐1‐ethyl‐N′‐[(1H‐imidazol‐3‐yl)methylidene]‐7‐methyl‐4‐oxo‐1,4‐dihydro‐1,8‐naphthyridine‐3‐carbohydrazidato}] dichloride methanol tetrasolvate], {[Cu3(C16H15N6O2)2Cl2(CH3OH)2]Cl2·4CH3OH}n, with the (1H‐imidazol‐4‐yl)methylidene carbohydrazide derivative of nalidixic acid (denoted h4imi), is presented and its structure is compared to the density functional theory (DFT) optimized structure of free h4imi. The title structure presents an octahedral CuII ion on an inversion centre alternating along a polymer chain with a square‐pyramidal CuII ion, with the two CuII centres bridged by two chloride ligands. Hydrogen bonds involving chloride counter‐ions and methanol solvent molecules mediate the three‐dimensional packing of the polymer. Comparison of the geometrical results from the structure analysis with those derived from a DFT study of the free ligand reveal the differences that arise upon coordination. 相似文献
8.
Sergio A. Moya Juana Gajardo Juan C. Araya Jaime J. Cornejo Véronique Guerchais Hubert Le Bozec J. Carles Bayón Alvaro J. Pardey Pedro Aguirre 《应用有机金属化学》2008,22(8):471-478
Novel ruthenium (II) complexes were prepared containing 2‐phenyl‐1,8‐naphthyridine derivatives. The coordination modes of these ligands were modified by addition of coordinating solvents such as water into the ethanolic reaction media. Under these conditions 1,8‐naphthyridine (napy) moieties act as monodentade ligands forming unusual [Ru(CO)2Cl2(η1‐2‐phenyl‐1,8‐naphthyridine‐ kN )(η1‐2‐phenyl‐1,8‐naphthyridine‐kN′)] complexes. The reaction was reproducible when different 2‐phenyl‐1,8‐naphthyridine derivatives were used. On the other hand, when dry ethanol was used as the solvent we obtained complexes with napy moieties acting as a chelating ligand. The structures proposed for these complexes were supported by NMR spectra, and the presence of two ligands in the [Ru(CO)2Cl2(η1‐2‐phenyl‐1,8‐naphthyridine‐ kN )(η1‐2‐phenyl‐1,8‐naphthyridine‐kN′)] type complexes was confirmed using elemental analysis. All complexes were tested as catalysts in the hydroformylation of styrene showing moderate activity in N,N′‐dimethylformamide. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
9.
KOTESWARA RAO Valasani SUBBA REDDY Sanapalli DADA PEER Echchukattula JANARDHAN RAO Alahari NAGA RAJU Chamarthi 《中国化学》2009,27(12):2379-2384
Iminophosphocins 8a – 8e and 9a – 9e were synthesized in four‐step reactions via Staudinger reaction. 3‐(Bromomethyl)‐1,2,3,4,5‐pentahydro‐3λ5‐naphtho[1,8‐f,g][1,5,3]diazaphosphocin‐3‐one ( 3 ) was prepared by reacting tris(bromomethyl)phosphineoxide ( 1 ) with 1,8‐diaminonaphthalene ( 2 ) in the presence of triethylamine (TEA) in dry tetrahydrofuran (THF), and treated with L‐valine methyl ester ( 4 ) and bis(2‐chloroethyl)amine ( 5 ) in the presence of TEA in dry THF to get 3‐methyl‐2‐[(3‐oxo‐1,2,3,4,5‐pentahydro‐3λ5‐naphtho[1,8‐f,g][1,5,3]diazaphosphocin‐3‐yl)methylamino]butanoate ( 6 ) and 3‐[di(2‐chloroethyl)aminomethyl]‐1,2,3,4,5‐pentahydro‐3λ5‐ naphtho[1,8‐f,g][1,5,3]diazaphosphocin‐3‐one ( 7 ). The compounds 6 and 7 were treated with trichlorosilane (SiCl3H) in dry tetrahydrofuran (THF) to form the trivalent P(III) intermediates 8 and 9 , which were further treated with various alkyl azides in dry THF in 55–60°C to afford the title compounds 8a – 8e and 9a – 9e . Their structures were established by multi‐nuclear NMR and mass spectra. All the newly synthesized compounds were found to possess moderate anti‐microbial activity. 相似文献
10.
《Journal of heterocyclic chemistry》2017,54(6):3696-3699
5,6‐Diaminopyrimidin‐2,4‐diol 1 was reacted with 1,4‐d ‐gluconolactone 2 , 6‐chloro‐4‐cyclopropyl‐7‐floro‐1,4‐dihydro‐1‐oxonaphthalen‐2‐carboxilic acid 4 , (3S)‐9,10‐difloro‐3,7‐dihydro‐3‐methyl‐7‐oxo‐2H‐[1,4]oxazino[2,3,4‐ij]quinolin‐6‐carboxylic acid 6 , and dimethylacetylendicarboxylate to afford 1‐(2,6‐dihydroxy‐9H‐purin‐8‐yl)‐sorbitol 3 , 7‐chloro‐1‐cyclopropyl‐6‐flouro‐3‐(2,6‐dihydroxy‐9H‐purin‐8‐yl)quinoline‐4(1H)‐one 5 , 9,10‐difluoro‐2,3‐dihydro‐6‐(2,6‐dihydroxy‐9H‐purin‐8‐yl)‐3‐methyl‐[1,4]oxazine[2,3,4‐ij]quinoline‐7‐one 7 , and (2,4‐dihydroxy‐6‐oxo‐5,8‐dihydro‐6H‐pteridine‐7‐yiliden)‐acetic acid methyl ester 9 , respectively. The synthesized compounds characterized by IR, 1H‐NMR, 13C‐NMR, GC‐mass, and elemental analysis. 相似文献
11.
1,2‐Dihydro‐2‐imino‐6‐(2‐imino‐2H‐chromen‐3‐yl)‐1,4‐diphenyl‐pyridine‐3‐carbonitrile 4 has been synthesized and reacted with ethyl cyanoacetate to yield the new 5‐amino‐1,7‐dihydro‐2‐(2‐imino‐2H‐chromen‐3‐yl)‐7‐oxo‐1,4‐diphenyl‐1,8‐naphthyridine‐6‐carbonitrile 6 , which consider a good and available starting intermediate for synthesis of series of functionalized chromenes. So, the compound 6 was utilized as a key for the synthesis of some new pyrimido[5,4‐c][1,8]naphthyridinones, pyrido[2,3‐c][1,6]naphthyridinones, triazolo[3′,4′:1,6]triazino][5,4‐c][1,8]naphthyridinones, triazolo[2′,3′:1,6]pyrimido[4,5‐c][1,8]naphthyridinones, triazepino[6,5‐c][1,8]naphthyridinone, and triazino[5,4‐c][1,8]naphthyridinones. The structures of these compounds were established by elemental analysis, IR, MS, and NMR spectral analysis. J. Heterocyclic Chem., (2012). 相似文献
12.
Novel dimeric Cu(II) heterochelates were synthesized using 1‐cyclopropyl‐6‐fluoro‐4‐oxo‐7‐piperazin‐1‐yl‐1,4‐dihydro‐quinoline‐3‐carboxylic acid (Cpf) and eight different neutral bidentate ligands. All ligands were characterized by elemental analyses, melting point and IR, 1H NMR and 13C NMR spectra, while heterochelates were characterized by elemental analyses, IR spectra, reflectance spectra, magnetic measurements and thermogravimetric analyses. The DNA interaction and cleavage behaviors of the ligands and corresponding heterochelates were studied by UV–vis absorption titration and gel electrophoresis technique, respectively. The results indicate that heterochelates show larger DNA interaction and cleavage affinity than the ligands. The antimicrobial activities of heterochelates, ligands, cupric nitrate and standard drugs against six bacteria and three fungi were tested. Copyright © 2007 John Wiley & Sons, Ltd. 相似文献
13.
《Magnetic resonance in chemistry : MRC》2002,40(7):467-470
In the course of saponification experiments with bis(2‐cyanoethyl) 2,6‐dimethyl‐4‐(2‐nitrophenyl)‐1,4‐dihydro‐3,5‐pyridinedicarboxylate ( 1 ), an analogue of the calcium channel blocker nifedipine, three unexpected degradation products were isolated. The compounds were identified as 3‐(2‐acetamido‐1‐carboxy‐1‐propenyl)‐1‐hydroxy‐2‐indolecarboxylic acid ( 3 ), 9‐hydroxy‐1,3‐dimethyl‐β‐carboline‐4‐carboxylic acid ( 4 ) and 6‐hydroxy‐2,4‐dimethyl‐5‐oxo‐5,6‐dihydrobenzo[c][2,7]naphthyridine‐1‐carboxylic acid ( 6 ). The structures of these compounds were deduced from one‐ and two‐dimensional 1H, 13C and natural abundance 15N NMR experiments (1H,1H‐COSY, gs‐HSQC, gs‐HMBC, 15N gs‐HMBC), and corroborated by comparison of their NMR data with the respective data for structurally similar compounds. Copyright © 2002 John Wiley & Sons, Ltd. 相似文献
14.
Masood Parvez Saeed Arayne Najma Sultana Ahsan Zamir Siddiqi 《Acta Crystallographica. Section C, Structural Chemistry》2004,60(4):o281-o283
The structure of the title compound, 1‐ethyl‐6‐fluoro‐1,4‐dihydro‐4‐oxo‐7‐(piperazin‐4‐ium‐1‐yl)‐1,8‐naphthyridine‐3‐carboxylate trihydrate, C15H17FN4O3·3H2O, has a zwitterion of enoxacin and three water molecules in the asymmetric unit. The zwitterions form sheets lying parallel to each other and are hydrogen bonded in a head‐to‐tail manner. The crystal structure is stabilized by the involvement of O and H atoms from all the water molecules in strong hydrogen bonds. The naphthyridine ring system is essentially planar, with the carboxylate group lying out of this plane at an angle of 26.13 (6)° and the ethyl group oriented at approximately right angles to this plane. The piperazinium ring adopts a chair conformation. 相似文献
15.
Ahmed A. Fadda Hassan A. Etman Mohamed Y. El‐Seidy Khaled M. Elattar 《Journal of heterocyclic chemistry》2012,49(4):774-781
The starting (1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)carbonohydrazonoyl dicyanide ( 2 ) was used as key intermediate for the synthesis of 3‐amino‐2‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐ylazo)‐[3‐substituted]‐1‐yl‐acrylonitrile derivatives ( 3 – 10 ). In addition, nitrile derivative 2 reacted with hydrazine hydrate or malononitrile to afford the corresponding 3,5‐diaminopyrazole 11 and enaminonitrile derivative 13 , respectively. On the other hand, compound 3 was subjected to react with malononitrile, acetic anhydride, triethylorthoformate, N,N‐dimethylformamide (DMF)‐dimethylacetal, thiourea, and hydroxylamine hydrchloride to afford antipyrine derivatives 16 – 21 . Moreover, the reaction of enaminonitrile 3 with carbon disulfide in pyridine afforded the pyrimidine derivative 22 , whereas, in NaOH/DMF followed by the addition of dimethyl sulphate afforded methyl carbonodithioate 24 . The reaction of enaminonitrile derivatives 3 – 5 with phenylisothiocyanate afforded the thiopyrimidine derivatives 25a – c . Finally, the enaminonitrile 4 reacted with 3‐(4‐chloro‐phenyl)‐1‐phenyl‐propenone to afford the pyridine derivative 27 . The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 13C‐NMR, 1H–NMR, and MS). 相似文献
16.
The fluoroquinolone family member ciprofloxacin is well known for its drug design and coordinating ability towards metal ions. The coordination chemistry of this drug with metal ions of biological and pharmaceutical importance is of considerable interest. Novel Mn(III) mixed‐ligand complexes of ciprofloxacin with various bis‐pyrazolone‐based dinegative bidentate ligands were synthesized and characterized on the basis of their physical properties, magnetic susceptibility measurements, (FT‐IR and electronic) spectral studies. The FAB‐mass spectrum of [Mn(A9)(L)(H2O)2]·H2O [where H2A9 = 4,4′‐(p‐tolylmethylene)bis(3‐methyl‐1‐phenyl‐4,5‐dihydro‐1H‐pyrazol‐5‐ol) and HL = 1‐cyclopropyl‐6‐fluoro‐4‐oxo‐7‐(piperazin‐1‐yl)‐1,4‐dihydroquinoline‐3‐carboxylic acid] was determined. All the synthesized compounds were screened for their bioactivity. The mixed‐ligand complexes exhibited comparable activities against two Gram‐negative (Escherichia coli and Serratia marcescens) and two Gram‐positive (Staphylococcus aureus and Bacillus subtilis) microorganisms. Copyright © 2011 John Wiley & Sons, Ltd. 相似文献
17.
A facile synthesis of a series of new quinoline‐8‐carbaldehyde compounds, namely 8‐formyl‐2‐(phenoxymethyl)quinoline‐3‐carboxylic acids ( 4a – 4h ) and 13‐oxo‐6,13‐dihydro[1]benzoxepino[3,4‐b]quinoline‐8‐carbaldehyde ( 5a – 5g ) is described, involving the one‐pot synthesis reaction of ethyl 2‐(chloromethyl)‐8‐formylquinoline‐3‐carboxylate ( 3 ) with substituted phenols followed by the intramolecular cyclization reaction via the treatment with polyphosphoric acid (PPA). Quinoline‐8‐carbaldehydes 4a – 4h and 5a – 5g are novel and their structures were supported by IR, 1H NMR, 13C NMR, MS and elemental analysis. 相似文献
18.
A simple and versatile methodology to synthesise 4‐hydroxy‐1H‐[1,2,4]triazino[4,5‐a]quinoline‐1,6(2H)‐dione from methyl 6‐fluoro‐4‐oxo‐1,4‐dihydro‐2‐quinolinecarboxylate has been developed. It involves car‐bohydrazide formation followed by a condensation with triphosgene to form the fused [1,2,4]triazino ring. In addition, the reactivity of the [1,2,4]triazino ring has been studied. 相似文献
19.
The synthetic route of sildenafil promoted us to synthesize new object molecules. New analogues containing a 4-thiazolidinone ring bonded to the phenyl moiety at the 2-position, 7-(substituted anilino)-6-fluoro-2-(p-meth- oxy-m-{[2-(p-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]aminocarbonyl}phenylsulfonamido)benzothiazoles (4a—4l) have been synthesized by cyclization with thioglycollic acid of Schiff bases 3a—3l from corresponding 7-(substituted anilino)-6-fluoro-2-(p-methoxy-m-hydrazinocarbonyl phenylsulfonamido)benzothiazoles (2a—2l). Compounds 2a—2l in turn were prepared by dehydroxyhalogenation followed by condensation with hydrazine hydrates of acids 1a—1l. Compounds 1a—1l in turn were prepared by chlorosulfonation of o-methoxy benzoic acid followed by condensation with 6-fluoro-7-(substituted anilino)-2-aminobenzothiazoles. Final compounds have been characterized by their elemental analysis, IR, NMR and mass spectra. All the synthesized compounds have been screened for their antimicrobial activities. Some of them showed good activities. 相似文献
20.
Dolors Edmont Christophe Marot Jacques Chenault 《Journal of heterocyclic chemistry》2002,39(6):1161-1165
A versatile methodology to build the 1H‐[1,2,4]triazino[1,6‐a]quinoline‐2,4,6(3H)‐trione structure from methyl 6‐fluoro4‐oxo‐1,4‐dihydro‐2‐quinolinecarboxylate was developed. The method involves an N‐ami‐nation followed by condensation of an aroyl isocyanate to form an alpha semicarbazidocarboxylate that readily cyclizes to the fused [1,2,4]triazino ring under ammonia/ethanol condition. Also, the reactivity of the [1,2,4]triazino ring thus obtained was studied. 相似文献