15793-77-8Relevant articles and documents
Spectroscopic and physicochemical studies on nickel(II) complexes of isatin-3,2′-quinolyl-hydrazones and their adducts
Gupta, Lokesh Kumar,Bansal, Usha,Chandra, Sulekh
, p. 972 - 975 (2007)
Nickel(II) complexes of isatin-3,2′-quinolyl-hydrazones of the type [Ni(L)X] (where X = Cl-, Br-, NO3-, CH3COO- and ClO4-] and their adducts Ni(L)X·2Y [where Y = pyridine or dioxane and X = Cl-, Br-, NO3- and ClO4-] have been synthesized under controlled experimental conditions and characterized by using the modern spectroscopic and physicochemical techniques viz. mass, 1H NMR, IR, electronic, elemental analysis, magnetic moment susceptibility measurements and molar conductance, etc. On the basis of spectral studies a four coordinated tetrahedral geometry is assigned for Ni(L)X type complexes whereas the adducts (Ni(L)X·2Y) were found to have a six coordinated distorted octahedral geometry.
A fluorescent dissymmetric thiosemicarbazone ligand containing a hydrazonequinoline arm and its complexes with cadmium and mercury
Calatayud, David G.,Lopez-Torres, Elena,Mendiola, M. Antonia
, p. 80 - 90 (2013)
A new dissymmetric thiosemicarbazone ligand containing a hydrazonequinoline arm, H2AMeTsQ, and its chloride salt, [H3AMeTsQ]Cl, were synthesized. Nine new complexes of cadmium and mercury with different structural characteristics were obtained under different reaction conditions as the ligand charge can be controlled by varying the amount of base. 113Cd and 199Hg NMR spectroscopy together with X-ray diffraction indicated that the complexes form monomeric and dimeric structures and even a coordination polymer. Fluorescence spectroscopy showed that both protonated and neutral forms of the ligand were fluorescent as well as some of their cadmium and mercury derivatives. The fluorescence intensity decreased upon complexation and in some complexes a shift of the emission maximum was also observed.
1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA
Hebenbrock, Marian,Müller, Jens
, p. 885 - 893 (2018)
Two new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ium (1a)+ and 1-phenyl-3-(6-phenylpyridin-2-yl)-3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium (1b)+, were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of E- and Z-configured N,N-functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of (1a)+ and (1b)+, respectively. The intercalative binding of (1a)PF6 and (1b)PF6 to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.
Spectroscopic approach in the characterization of the copper(II) complexes of isatin-3,2′-quinolyl-hydrazones and their adducts
Gupta, Lokesh Kumar,Bansal, Usha,Chandra, Sulekh
, p. 463 - 466 (2006)
Copper(II) complexes of isatin-3,2′-quinolyl-hydrazones of the type [Cu(L)X] (where X = Cl-, Br-, NO3-, CH3COO- and ClO4-] and their adducts Cu(L)X.2Y [where Y = pyridine or dioxane and X = Cl-, Br-, NO3- and ClO4-] have been synthesized under controlled experimental conditions and characterized by using the modern spectroscopic and physicochemical techniques viz. IR, electronic, EPR, elemental analysis, magnetic moment susceptibility measurements and molar conductance, etc. On the basis of spectral studies a four coordinated square planer geometry is assigned for Cu(L)X type complexes whereas the adducts (Cu(L)X.2Y were found to have a six coordinated octahedral geometry.
Hesperidin quinazoline hydrazone derivative with anti-tumor activity and preparation method and application thereof
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Paragraph 0020; 0032-0037, (2021/12/08)
The invention discloses an orange peel quinoline hydrazone derivative with anti-tumor activity and a preparation method and application thereof, and the molecular formula is C. 25 H21 N3 O5 MTT Shows the antitumor activity of the hesperidin -4 - quinazoline hydrazone derivative of the invention, and the experimental result shows that the derivative of the invention is BGC - 823 for human gastric cancer cells. The proliferation of human hepatoma cell BEL - 7402, human lung cancer cell A549 and human breast cancer cell MCF - 7 is inhibited, compared with hesperetin itself, activity is increased by 2-4 times, activity is greatly enhanced, and especially BEL - 7402 cells are more sensitive and IC. 50 The value is 10.97 μm . and the hesperidin -4 - quinoline hydrazone disclosed by the invention has a good inhibition effect on four tumor cells of the experiment, the inhibition activity is stronger than that of the corresponding crude drug hesperetin itself, and especially the inhibition activity of human liver cancer cells BEL - 7402 is nearly 4 times.
Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source
Liu, Lingfeng,Qiao, Chunhua,Shen, Bei,Xu, Yiwen
supporting information, (2020/04/01)
1,2,4-Triazolo[3,4-a]pyridines and related heterocycles and substituted triazines were commonly discovered scaffolds in a variety of pharmaceutical and agrochemical agents. Herein, we report a highly efficient and practical method using DMF and its derivative for the [4+1] and [5+1] annulation reactions to prepare these heterocycles. This metal free reaction takes advantages of shelf stable DMF as solvent and carbon donor, imidazole chloride as a catalyst, the mild reaction condition tolerates a broad substrate range and substitutes. The prepared 3-unsubstituted 1,2,4-triazolo[3,4-a]pyridine and derivatives allow further introduction of a variety of functional group1 at 3-position.
Synthesis, characterization and evaluation of anti-inflammatory and analgesic activity of some novel quinoline based thiazolidinone heterocycles
Amer, Atef M.,Deeb, Ali,El-Eraky, Wafaa I.,El Awdan, Sally A.,Mahgoub, Sebaey
, p. 67 - 77 (2019/03/28)
IN (13–22) this paper in a three-step we report process. the synthesis Condensation of some quinoline of 2-hydrazinylquinoline based thiazolidinone 2 with derivatives different aromatic aldehydes gave the corresponding Schiff bases 3-10 which in turn were reacted with thioglycolic acid to furnish the corresponding thiazolidinone derivatives 13-20. Reaction of compound 2 with isatin or methyl isatin gave 1-sustituted-3-(2-(quinolin-2-yl)hydrazono) indolin-2-ones 11 and 12, which were converted to 1-substituted 3'-(quinolin-2-ylamino) spiro[indoline-3,2'-thiazolidine]-2,4'-dione 21 and 22 by cyclocondensation with thioglycolic acid. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1H NMR and MS. Furthermore, all new thiazolidinone derivatives were evaluated for their anti-inflammatory and analgesic activity. The Study results revealed that the highest anti-inflammatory potency was gained by 6 derivatives according to the following order 22 > 17 >13 > 14 > 21 > 15, showing a good edema inhibition compared to the reference drug indomethacin. Compound 22 carrying indole ring system inhibited the edema volume significantly at the 1st h post administration, and the activity was enhanced up to the 4th h giving a promising edema volume inhibition compared to that produced by indomethacin. The longest duration of analgesic action up to 90 min post compounds administration was obtained by the compounds 13, 17 and 22, they exhibited potent analgesia compared to that obtained by aspirin.
Synthesis, characterization and antimicrobial activity of some novel quinoline derivatives bearing pyrazole and pyridine moieties
Amer, Atef M.,El-Eraky, Wafaa I.,Mahgoub, Sebaey
, p. 1 - 8 (2019/12/24)
I N continuation of our interest in synthesis of novel quinoline derivatives with anticipated biological activity, we have synthesized new quinoline derivatives bearing pyrazole and pyridine moieties by formylation of quinoline hydrazones through the Vilsmeier-Haack reaction which is a common method for the synthesis of 4-formyl pyrazoles. Condensation of 2-hydrazinylquinoline 1 with 4-substituted acetophenone gave the corresponding hydrazones 2a–c which in turn underwent the Vilsmeier-Haack reaction in POCl3/DMF to furnish the corresponding 4-formyl pyrazole derivatives 3a–c. One-pot reaction of compounds 3a–c with malononitrile and thiophenol or ethyl mercaptan gave the 3,5-pyridine dicarbonitrile derivatives 11a–f. The synthesized derivatives were screened for their antimicrobial activities against Gram negative bacteria, Gram positive bacteria and Fungi. Most of compounds showed excellent antimicrobial activities compared to the reference drugs. All the newly synthesized compounds have been characterized by means of elemental analyses, IR, 1H NMR and MS.
Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents
El Shehry, Mohamed F.,Ghorab, Mostafa M.,Abbas, Samir Y.,Fayed, Eman A.,Shedid, Said A.,Ammar, Yousry A.
, p. 1463 - 1473 (2017/11/10)
In an attempt for development of new antimicrobial agents, three series of quinoline derivatives bearing pyrazole moiety have been synthesized. The first series was synthesized through the synthesis of 4-(quinolin-2-yloxy)benzaldehyde and 4-(quinolin-2-yloxy)acetophenone and then treatment with ketone or aldehyde derivatives to afford the corresponding chalcones. Cyclization of the latter chalcones with hydrazine derivatives led to the formation of new pyrazoline derivatives. The second series was synthesized via the synthesis of 2-hydrazinylquinoline and then treatment with formylpyrazoles to afford the corresponding hydrazonyl pyrazole derivatives. The third series was synthesized through the treatment of 2-hydrazinylquinoline with ethoxyethylidene, dithioacetal and arylidene derivatives to afford the corresponding pyrazole derivatives. The synthesized compounds were evaluated for their expected antibacterial and antifungal activities; where, the majority of these compounds showed potent antibacterial and antifungal activities against the tested strains of bacteria and fungi. Pyrazole derivative 13b showed better results when compared with the reference drugs as revealed from their MIC values (0.12–0.98 μg/mL). The pyrazole derivative 13b showed fourfold potency of gentamycin in inhibiting the growth of S. flexneri (MIC 0.12 μg/mL). Also, compound 13b showed fourfold potency of amphotericin B in inhibiting the growth of A. clavatus (MIC 0.49 μg/mL) and C. albicans (MIC 0.12 μg/mL), respectively. The same compound showed twofold potency of gentamycin in inhibiting the growth of P. vulgaris (MIC 0.98 μg/mL), equipotent to the ampicillin and amphotericin B in inhibiting the growth of S. epidermidis (MIC 0.49 μg/mL), A. fumigatus (MIC 0.98 μg/mL), respectively. Thus, these studies suggest that quinoline derivatives bearing pyrazole moiety are interesting scaffolds for the development of novel antibacterial and antifungal agents.
Synthesis and Characterization of 2-Pyridinylmethylene-2-quinolyl Hydrazone Cobalt(III) Complexes. Reactivity Trends and Solvent Effect on the Initial and Transition States of Base Catalyzed Hydrolysis
Mohamad, Ahmad Desoky M.
, p. 1575 - 1595 (2017/09/06)
The complexes of pyridine-2-aldehyde-2-quinolylhydrazone Co(III) nitrate [Co(paqh)2](NO3)2, methyl-2-pyridylketone-2-quinolinhyrazone Co(III) nitrate [Co(mpkqh)2](NO3)2, and phenyl-2-pyridylketon-2-quinolinhyrazone Co(III) nitrate [Co(ppkqh)2](NO3)2 were prepared and characterized. Solubilities of Co(III)–hydrazone complexes were measured. Transfer chemical potentials were calculated from the measured solubilities of the Co(III) complexes in aqueous methanol mixtures at 25?°C. The reactivity trends in the transfer chemical potentials are discussed in terms of the nature of the bonded ligands. Kinetics of the base hydrolysis of Co(III)–hydrazone complexes in the aqueous methanol mixtures have been studied at 25?°C, and follow the rate law kobs?=?k2[OH?]. The solvent effects on the reactivity trends of Co(III) complexes are analyzed into initial state (is) and transition states (ts) components. The reaction rates are reduced by the increase of methanol content. The destabilization of the transition state is remarkable compared to the initial state in the aqueous methanol mixtures. The initial state is more hydrophobic in nature than the transition state for Co(III) complex reactions.
