Novel 1,4-naphthoquinone N-aroylthioureas: Syntheses, crystal structure, anion recognition properties, DFT studies and determination of acid dissociation constants (original) (raw)
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Journal of Chemical Sciences, 2012
The new series of N-, SO O-substituted 1,4-naphthoquinone and SO O-substituted 1,4benzoquinone compounds were synthesized via vinylic substitution. Compounds 3 and 4 were synthesized from the reaction of 1 with 2. Compounds 6, 7 and 8 were synthesized from reaction of 1 with 5. Compounds 10 and 11 were obtained from the reaction of 1 with 9. Compounds 13 and 14 were synthesized from the reaction of 1 with 12. Compounds 16 and 17 were obtained from the reaction of 15 with 2. Photochemical and electrochemical properties of N-, SO O-substituted quninone compounds were determined by using fluorescence spectroscopy and cyclic voltammetry. Crystal structure of 2-(7-sulphanyl-4-methyl-coumarinyl)-3-(1-ethoxy)-1,4-naphthoquinone 13 was determined by X-ray diffraction method.
Novel 2-Amino-3-(2,4-dinitrophenylamino) Derivatives of 1,4-Naphthoquinone
ChemInform, 2005
The strong electron withdrawing nature of a 2,4-dinitrophenylamino group when attached to a chloro-naphthoquinone enhances the displacement of the chlorine atom by various aliphatic, cyclic and aromatic amines. A new series of 2-amino-3-(2,4dinitrophenylamino) derivatives of 1,4-naphthoquinone were prepared. Three absorption maxima in the UV-vis spectra were typical, including one at 430-550 nm assigned to a CT transition.
Journal of Molecular Structure, 2021
A novel series of 1,4-naphthoquinones substituted containing sulfur, nitrogen, oxygen atoms were synthesized. The structures of the novel products were characterized by using the various spectroscopic techniques such as 1 H nuclear magnetic resonance (NMR), 13 C NMR, mass spectrometry (MS), Fourier transform infrared spectroscopy (FT-IR) and microanalysis. The crystal structures of 2,3-bis(benzylsulfanyl)-1,4napthoquinone 4 and 2,3-bis(ethylsulfanyl)-1,4-naphthoquinone 7 were determined by using X-ray single crystal diffraction method. Electrochemical behaviors of some 1,4-naphthoquinone (NQ) derivatives 3, 4,
Inorganica Chimica Acta, 2008
Two carboxyl substituted quinones and their ethyl esters were prepared by alkylation of 2-methyl-1,4-naphthoquinone (MNQ), also known as menadione or vitamin K 3 . All products were characterized by spectroscopic ( 1 H NMR, 13 C NMR, IR) and electrochemical (cyclic voltammetry) methods, and the crystal structure of the two carboxylic derivatives was also determined. Both carboxyl substituted quinones crystallize in the P 1 system as hydrogen bonded dimers. In MeCN, the cyclic voltammograms of the ester derivatives present two reversible one-electron redox waves very similar to those of the parent quinone, MNQ. However, in the same solvent, the corresponding carboxyl substituted quinones show one cathodic and one anodic additional irreversible waves at more positive potentials and a decrease in current intensity of the two quinone reduction waves accompanied by loss of the quasi-reversible character of the second wave. These results show that the presence of the carboxylic substituent does not greatly modify the redox behaviour of the quinone, except for a small anodic shift of the potentials, but the associated presence of H + ions in solution causes an important perturbation to the system, stabilizing the electrogenerated semiquinones by intermolecular self-protonation and/or hydrogen bonding.
Novel N,S-Substituted naphthoquinone analogues from aminonaphthoquinones
The European Chemistry and Biotechnology Journal, 2024
In this study, novel N,S-substituted naphthaquinone analogues (2, 4, 6, and 8) were synthesized from the reactions of previously known aminonaphthaquinone derivatives (1, 3, 5, and 7) with allyl mercaptan. 2-(allylthio)-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione (2), 2-(allylthio)-3-(4-(2fluorophenyl)piperazin-1-yl)naphthalene-1,4-dione (4), 2-(allylthio)-3-(4-benzylpiperidin-1yl)naphthalene-1,4-dione (6) and 2-(4-chlorophenylamino)-3-(allylthio)naphthalene-1,4-dione (8) were obtained from the reactions of 2-chloro-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione (1), 2-chloro-3-(4-(2-fluorophenyl)piperazin-1-yl)naphthalene-1,4-dione (3), 2-(4-benzylpiperidin-1-yl)-3chloronaphthalene-1,4-dione (5), and 2-(4-chlorophenylamino)-3-chloronaphthalene-1,4-dione (7) with allyl mercaptan according to the general synthesis procedure. Synthesized new naphthaquinone analogues (2, 4, 6, and 8) were purified by column chromatography. The chemical structures of these novel N,S-substituted naphthaquinone analogues were characterized by spectroscopic methods (FT-IR, NMR, and MS).
Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives
Journal of the Turkish Chemical Society, Section A: Chemistry, 2017
In this study, some new sulfanyl-substituted amino 1,4-naphthoquinone derivatives which possess two electron-donating groups in the amino fragment were synthesized and their structures were analyzed by spectroscopic techniques. First, 2-chloro-3-[(2,4dimethoxyphenyl)amino]naphthalene-1,4-dione (3a) and 2-chloro-3-[(3,5dimethoxyphenyl)amino]naphthalene-1,4-dione (3b) were obtained from the reactions of dichloro-1,4-naphthoquinone (1) with 2,4-dimethoxyaniline and 3,5-dimethoxyaniline. In the following step, the compounds 3a,b were reacted with aliphatic nucleophiles; ethyl-, 1-propyl-, and 1-pentyl mercaptan. S-nucleophiles attacked the carbon atom of 1,4-naphthoquinone core and displaced the chlorine atom to create target molecules; 2-arylamino-3-(ethylthio)naphthalene-1,4-dione (5a,b), 2-arylamino-3-(propylthio)naphthalene-1,4-dione (5c,d), 2-arylamino-3-(pentylthio)naphthalene-1,4-dione (5e,f) derivatives. The structures of the synthesized compounds were elucidated by utilizing 1D and 2D NMR techniques with additional spectroscopic data (mass and FTIR).
Synthesis and Study of Naphthoquinones Derivatives
Applied Mechanics and Materials, 2016
In this research, we reported the study and synthesis of naphthoquinones intermediate compounds lead to the target naphthoquinones derivatives product. Naphthoquinones derivatives have long been known to display anticancer and antimalarial activity in addition to a wide variety of other bioactivities. Moreover, it has been reported to possess antimalarial disease against Plasmodium falciparum. The naphthoquinones derivatives product (5) were synthesized by coupling with 2-(3-bromo-2,2-dimethylpropyl)-1-methoxynaphthalene (4) and methyl ketone fatty acid (3). The 2-(3-bromo-2,2-dimethylpropyl)-1-methoxynaphthalene (4) was constructed by 1-hydroxy-2-naphthoic acid (1) in 5 steps with good to excellent yield. The synthetic pathway was started with the methylation provided the methyl ester naphthoquinones compound in 93% yields. Then, the reduction of methyl ketone by using LiAlH4 gave the alcohol compound in 90% yields. Methyl alcohol was changed to the alkyl bromide using PBr3 in 75% ...
Design, Synthesis and Evaluation of Some Novel1, 4-Naphthoquinone Derivatives to TreatCancer
IIT (BHU) varanasi, 2019
Objective: In the present study, a series of nineteen compound of 1-phenyl-3-(5-phenyl-1H-imidazol-1-yl) thiourea derivatives (5a-9b) were designed, synthesized, characterized by physicochemical and spectral data (IR, 1H NMR, and mass spectroscopy) and evaluated for their Anti-HIV activity with the aim to develop novel substituted imidazole derivatives with broad-spectrum chemotherapeutic properties. Methods: Compounds (5a-9b) were designed by using Glide 5.0 to carry out binding mode analysis of N-substituted imidazoles against reverse transcriptase enzyme of wild type as well as resistant strains of HIV-1 virus with PDB ID: 1RT2, synthesized by reacting various substituted anilines and substituted phenacyl bromides in four steps and evaluated their anti HIV activity as well as cytotoxicity assay through MTT colorimetric measure. Results: Compounds 6a, 6b, 6c, 6d, 7c, 9a and 9b being the most active exhibited therapeutic index that were >22.4, 31.1, 30.5, 51.5, 34.6, 30.5 and 85.6 compared to Zidovudine (AZT) having therapeutic index (TI) 514342.6. Compound 9b showed the highest docking score-12.47 in the active site of the HIV protein of 1RT2 as well better in vitro anti-HIV activity.
Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives
Journal of Chemical Crystallography, 2011
The structures of sulphur atom tethered quinone containing flexible carboxylic acid (3-methyl-1,4-dioxo-1, 4-dihydronaphthalen-2-ylsulfanyl)acetic acid (1) and its molecular complex with 4,4 0-bipyridine (3) are determined. The compound 1 crystallizes in P-1 (triclinic, a = 7.5378(6) Å , b = 7.6413(7) Å , c = 10.3101(9) Å ; a = 89.779 (7)°, b = 81.042 (5)°, c = 89.101(7)°) and the molecular complex 3 crystallises in P2(1)/n (monoclinic, a = 9.3383(7) Å , b = 3.970(3) Å , c = 42.130(3) Å , b = 91.056(5)°) space groups, respectively. The R 2 2 (8) type hydrogen bonding between dicarboxylic acid groups present in the parent compound 1 is lost on interaction with 4, 4 0-bipyridine; in the molecular complex 3 R 2 2 (7) type of OÁÁÁH-C and O-HÁÁÁN interactions are present between the pyridine rings and carboxylic acid groups. The molecular complex (4) derived from 3-carboxymethylsulfanyl-1,4-dihydroxynaphthalen-2-yl-sulfanyl) acetic acid (2) with triphenylphosphine oxide in 1:2 ratio, crystallises in C2/c space group have monoclinic, a = 26.0494(13) Å , b = 10. 5402(5) Å , c = 17.1023(8) Å , b = 108.719 (5)°). The triphenylphosphine oxide molecules are preferentially held by O-HÁÁÁO interactions between carboxylic acid and P=O bond.
Synthesis and characteristics of amino acid derivatives of 1,4-naphthoquinone
Synthesis optimization of a series of 2-amino acid-3-chloro-1,4-naphthoquinones demonstrated feasibility to conduct reactions in mild conditions providing relatively high yields, simple procedure and low time costs. Compounds were characterized with standard methods of chemical analysis and spectroscopic techniques. Physicochemical parameters of weight loss and start melting point were determined. Preliminary screening of synthesized compounds carried out with online based algorithm of prediction of activity spectra for synthesized substances (PASS).