Nahide Gülşah Deniz

Istanbul University-Cerrahpasa · Department of Chemistry

In this study, firstly, novel vitamin K3 analogs were synthesized by the reactions of vitamin K3 (2-methyl-1,4-naphthoquinone, also known as menadione) with some aromatic and heterocyclic ring substituted nucleophiles such as 2,4-dimethoxyaniline, 4-methoxyaniline, 4-benzylpiperidine and 1-(2-aminoethyl)piperazine in ethanol/Na2CO3, and 1-(diphenyl...

ABSTRACT 5-Chloro-2-hydroxybenzophenone-S-methyl-4-phenylthiosemicarbazone (Η2L1) was synthesized from 4-phenylthiosemicarbazide. Reaction of Η2L1 with [bis(acetylacetonato)dioxomolybdenum(VI)] gave the dioxomolybdenum(VI) complexes with [MoO2(L1)(L2)] composition where L2 is n-pentanol, ethylene glycol monomethyl ether, ethyl acetate, isoamyl alco...

The ketene dithioacetal 3 generated from 2-nitroperchlorobutadiene 1 reacted with various heterocyclic amines and aliphatic, aromatic and heterocyclic thiols to produce functionalized new ketene- N,S,S -acetals and S,S,S -acetals 4a-f, 5a-h as heterocyclic dithiolanes. They were separated/purified by chromatographic methods and their exact structur...

In this study, firstly, five novel vitamin K3 analogues were synthesized by the reactions of vitamin K3 (2-methyl-1,4-naphthoquinone, also known as menadione) with some aromatic and heterocyclic ring substituted nucleophiles such as 2,4-dimethoxyaniline, 4-methoxyaniline, 4-benzylpiperidine and 1-(2-aminoethyl)piperazine in ethanol/Na 2 CO 3 , and...

In this study, firstly, five novel vitamin K3 analogues were synthesized by the reactions of vitamin K3 (2-methyl-1,4-naphthoquinone, also known as menadione) with some aromatic and heterocyclic ring substituted nucleophiles such as 2,4-dimethoxyaniline, 4-methoxyaniline, 4-benzylpiperidine and 1-(2-aminoethyl)piperazine in ethanol/Na 2 CO 3 , and...

The novel N-,O-substituted-5-Nitro-1,4-naphthoquinones (NQ) as regioisomers were synthesized by reactions of 2,3-dichloro-5-nitro-1,4-naphthoquinone with some heterocyclic rings which were substituted with various nucleophiles according to a Michael 1,4-addition mechanism. All synthesized compounds were characterized by elemental analysis, electros...

The studies on nitronaphthoquinone derivatives are rare in the literature, and the nitro group associated with the aromatic ring in the quinone system is known to increase the biological activity of naphthoquinone due to its electron-withdrawing properties. In the course of quinone derivatives, the new N(H)-substituted-5-nitro-1,4-naphthoquinones (...

Researches with nitro compounds mainly relates to the synthesis of their derivatives used as unusual intermediate compounds. Because of their high reactivity in SNvin reactions, polyhalo-nitro-butadienes have been shown in many studies to have many properties as well as medical and pharmaceutical effects such as antitumor, bactericidal, fungicide a...

A series of disperse dyes, 9,10-anthraquinone containing dithiocarbamate, thiourea and triazole fragments, were prepared via consecutive refunctionalization of aminoanthraquinones in our previous studies and their structures were confirmed by the 1H, 13C NMR, IR spectra, LC-MS and elemental analysis data. The obtained compounds were applied on poly...

In this study, derivatives of new vitamin K3 were synthesized by the reactions of 2-methyl-1,4-naphthoquinone 1 with some heterocyclic ring substituted nucleophiles: 1-piperonylpiperazine 2, 1-(2-furoyl)piperazine 5, 1-(2-aminoethyl)piperidine 8, 1-(2-aminoethyl)pyrrolidine 10 and 2,6-dimethyl morpholine 12 in chloroform/triethylamine (TEA) or etha...

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 ¹H nuclear magnetic resonance (NMR), ¹³C NMR, mass spectrometry (MS), Fourier transform infrared spectroscopy (FT-IR) and microana...

The nitro group–substituted perhalogenobuta-1,3-diene (1) is important synthetic precursor in the synthesis of different heterocycles groups with high biological activity. Firstly, new N,S-substituted-perhalonitro-1,3-butadiene compounds were synthesized by the reactions of various amino or thiol containing nucleophiles with 1. The structures of al...

1,4-Naphthoquinones (1,4-NQ) have been reported to possess a variety of pharma-cological properties including antibacterial, antifungal, antiviral, anti-inflammatory, anti-artherosclerotic, and anticancer effects. In this study, new N- and S,S-substituted-1,4-NQ derivatives were synthesized in excellent yields and were completely characterized by s...

Breast cancer is the most-diagnosed cancer type among women. The triple-negative subtype is an especially aggressive type of breast cancer. Although chemotherapy is almost the only option for the treatment of triple-negative breast cancer (TNBC), currently used chemotherapeutics are not effective enough, considering the poor survival rate of patien...

In the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert-butylbenzylamine, N-(3-aminopropyl)-2-pipecoline, 2-amino-5,6-dimethylbenzothiazole, N,N'...

A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations...

In this study, new 1,4-naphtho- and 5-nitro-1,4-naphtho derivatives containing N- and N,N-substituted groups which has not been reported yet, have been synthesized from 2,3-dichloronaphthalene-1,4-diones (1,9). Compounds of 2-choloro-3-((2,4,6-triflorophenyl)amino)naphthalene-1,4-dione (3) and 2-chloro-3-((4-florophenyl)amino)naphtalene-1,4-dione (...

In this study, new piperazine derivatives were synthesized by the reactions of S-substituted-3-nitro-1,3-butadienes with some piperazine derivatives: (1-(2-furoyl)-, 1-(4-fluorobenzyl)-, 1-(3-fluorophenyl)-and 1-(1-tetrahydro-2-furyl)piperazine) in CHCl3 at room temperature. The structures of the new compounds were characterized by micro analysis,...

The new anthraquinonylhydrazones were obtained by the interaction of 9,10-dioxoanthracene-1-diazonium sulfates with a number of α- and β-carbonyl-containing compounds under modified conditions of the Japp–Klingemann reaction, and a probable mechanism of the formation has been proposed. It was found that hydrazones, unsaturated in the second positio...

An effective method for the synthesis of 1-anthraquinonyl hydrazones containing the acyl- and/or ethoxycarbonyl, carbo- and heterocyclic fragments in the ylidene moiety has been shown, which are convenient reagents for further chemical transformations. Investigation of the antioxidant activity of hydrazones has allowed to identify promising compoun...

Anticancer activity as an associated action for a series of dithiocarbamates of 9,10-anthracenedione was predicted using the PASS computer program and analysed with PharmaExpert software. The predicted cytotoxic activity of the dithiocarbamate derivatives of 9,10-anthracenedione was evaluated in vitro on cancer cells of the human lung (A549), prost...

In this study, a series of bis(thio)substituted-1,4-naphthoquinone compounds (4a-j) were synthesized via Michael addition reaction and their structures were determined by infrared spectrometry,¹H and¹³C nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis. The synthesized substances were applied to polyester fibers and...

A variety of new derivatives of 9,10-anthracenedione with mono- and bisdithiocarbamate moiety in the non-catalytic conditions have been synthesized. The obtained compounds were screened for their antioxidant capacity using the cupric-reducing antioxidant capacity (CUPRAC) method. Three of the compounds showed CUPRAC-Trolox equivalent antioxidant ca...

The aim of this study was synthesis of substituted naphthoquinone derivatives and testing of their dyeability on polyester fibers. There are few studies concerned with dyeing properties of heteroatom-substituted-1,4-naphthoquinone compounds in the literature. A series of N-, S-, O-substituted-1,4-naphthoquinone compounds were synthesized via vinyli...

The S-substituted nitrodienes were obtained by the reactions of polyhalo-3-nitrobutadiene 1 with some S-nucleophiles [4-(tert-butylbenzyl)thiol,4-chlorophenylthiol, ethylthiol, and cyclopentylthiol] in directly at room temperature. N,S-Substituted trichloronitrodienes were synthesized from the reactions of the S-substituted nitrodienes with some pi...

In the present paper, we report the synthesis, characterization, and biological evaluation as antifungal, antibacterial, antioxidant, and cytotoxic/anticancer agents of N-, S-, O-substituted-1,4-naphtho- and 2,5-bis(amino-substituted)-1,4-benzoquinone derivatives. In the synthesized compounds, antimicrobial activity at low concentrations against Es...

New complexes, [Fe(L)Cl], [Ni(L)], and [Zn(L)C2H5OH] (1-3), were synthesized by template reaction of 2-hydroxy-acetophenone-S-methyl-thiosemicarbazone with 2-hydroxy-benzaldehyde. The compounds were characterized by elemental analysis, magnetic measurements, FT-IR, 1H NMR, UV-visible, and ESI-MS spectra. In these complexes, the ligand is coordinate...

In the present study, we reported the one-pot synthesis of S,S- and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur- and oxygen-containing nucleophiles were investigated to obtain highly functionalized S,S- and...

5-Chloro-4-methyl-2-hydroxybenzophenone S-propyl-4-phenyl-thiosemicarbazone (H2L) and its cis-dioxomolybdenum(VI) complexes, in the general formula [MoO2(L)R-OH)] (R: methyl, 1; ethyl, 2; n-propyl, 3; n-butyl, 4; n-pentyl, 5), were synthesized and characterized by micro analysis, electronic, infrared and 1H and 13C NMR spectra. The crystal structur...

S,S- and S,S,S-substituted nitrodienes 3a, 3b and 4a were synthesized by reactions of 1,1,2,4,4-pentachloro-3-nitro-1,3-butadiene with some thiols 4-chlorobenzylmercaptan and 2-chlorobenzylmercaptan in ethanol in the presence of sodium hydroxide. Thiomorpholine ring substituted nitrodienes 6c and 6d and were obtained from the reactions of the mono(...

:Herein, we report the reactions of 1,1,2,4,4-pentachloro-3-nitro-1,3-butadiene 1a and (1Z)-1-bromo-1,2,4,4-tetrachloro-3-nitro-1,3-butadiene 1b with nitrogen- and sulfur-containing nucleophiles to obtain highly functionalized S-, S,S-, S,S,S-, S,O- and N,S-substituted-polyhalodiene-3-nitro-1,3-butadiene derivatives. Most of these reactions turned...

The reactions of polyhalo-2-nitro-1,3-butadiene with naphthalene-2-thiol and 4-methylbenzenethiol lead to highly functionalized poly(arylthio)-2-nitro-1,3-butadienes. The novel 4,4-dichloro-1,1,3-tris(2-naphthylthio)-2-nitro-1,3-butadiene (5a) and the known 4,4-dichloro-1,1,3-tris(4-methylphenylthio)-2-nitro-1,3-butadiene (5b) were synthesized by v...

The title compounds are synthesized by reactions of polyhalo-2-nitrobutadienes (I) and (XIII) with different amino- and thiol-nucleophiles.

Polyhalogenated-2-nitro-1, 3-butadienes are important synthetic precursors for a variety of polyfunctionalized bioactive heterocycles. Herein, we report the reactions of 1, 1, 3, 4, 4-pentachloro-2-nitro-1, 3-butadiene 1 and 4-bromo-1, 1, 3, 4-tetrachloro-2-nitro-1, 3-butadiene 2 with amino and thiol containing nucleophiles to obtain highly functio...

The new series of N-, S-, O-substituted 1,4-naphthoquinone and S-, O-substituted 1,4-benzoquinone 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. Com...

A series of N-(diphenylmethyl)piperazine, thiomorpholine and alkylthio substituted nitro-1,3-butadiene compounds have been synthesized and tested for their antimicrobial, antifungal activities and for evaluation of growth regulative action. Compounds 2b, 2c, 2d in 0.5% concentration showed moderate activity against Myc.luteum and C.tenuis. Biologic...

New S-,O-substituted naphthoquinone compounds (3a, 4b, 6, 7c, 9d, 10, 12, 13c, 14d, 15) were synthesized via vinilic substitution. 2,3-Dichloro-1,4-naphthoquinone gave 3a and 4b with 4,4′-thiobisbenzenethiol, respectively. Compounds 6 and 7c were obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with cyclohexylmercaptane. The compounds...

New S-and S,O-substituted 1,4-naphthoquinone compounds 3, 4 and 5 were synthesized from the reaction of 2,3-dichloro-1,4-naphtho-quinone (1) with 2-mercaptobenzylalcohol (2) in ethanol with sodium carbonate for 2 h at room temperature. The structures of novel compounds were characterized by using micro analysis, FT-IR, UV/Vis, 1H NMR, 13C NMR, mass...

The compound 4-bromo-3,4-dichloro-1-(1-morpholinyl)-1-(decylsulfanyl)-2-nitro-buta-1,3-diene was synthesized from the reaction of 4-bromo-1,3,4-trichloro-1-(decylsulfanyl)-2-nitro-buta-1,3-diene with morpholine and characterized by elemental analysis, IR spectrum, UV spectra, 1H NMR,13C NMR and X-ray single crystal determination. In the title compo...

The title compound, C17H19N3O2Cl3SF, consists of nitro substituted in the butadiene unit, the propylsulfanyl chain and the 4-(fluorophenyl)piperazine groups. The compound crystallizes in the triclinic space group P1, with unit cell parameters: a = 9.1823(5), b = 10.9865(8), c = 11.4414(5)Å, Z = 2, V = 999.31(12)Å3, R1 = 0.059. The butadiene unit is...

Mono(thio)substituted-1,3-nitrodiene compounds 3a-c give 5a, 5c, 7a, 7c, 9a, 9c, 11a, 11c, 13a, 13b with thiomorpholine 4 and piperazine derivatives 6, 8, 10, 12. The new compound 3a is synthesized from reaction of 1 with 2a. The compound 7b crystallizes in the monolinic crystal system (space group P 21/n) with the n-butyl group attached to S1 and...

The title compound, C18H14Cl3NO2S2, was synthesized by the reaction of 1,1,2,4-tetrachloro-4-(4-methylphenylsulfanyl)-3-nitrobuta-1,3-diene with ethanedithiol. The butadiene unit is not completely planar as would be expected if the two double bonds were fully conjugated The torsion angle of the butadiene unit is −82.2 (5)°.

The molecule of the title compound, C15H15Cl2NO3S3, is not planar. The butadiene group and the 4-methylphenyl ring are inclined at an angle of 57.9 (1)°.

The molecule of the title compound, C15H15Cl2NO3S3, is not planar. The butadiene group and the 4-methyl-phenyl ring are inclined at an angle of 57.9 (1)°.

Thiosubstituted nitrodien compounds 1a-f are obtained from 2-nitropentachlorobutadiene and some alifatic thiols. Compounds 1a-f have reacted with thiomorpholine 2 and yielded 3a-f in CH2Cl2. The compounds 5a-f have been obtained by the reactions of 1a-f with N-(diphenylmethyl)piperazine 4 in CH2Cl2. 2-Nitro-3,4,4-trichloro-1-(ethylthio)-1-[4-(1-dip...

In the title N,S-substituted compound, C24H26Cl3N3O2S, the butadiene unit assumes a configuration close to cisoid. The piperazine ring adopts a chair conformation.

In the title compound, C11H15Cl3N2O2S2, the thio­morpholine ring adopts a chair conformation and the butadiene has a conformation closer to cisoid than to transoid.

Tetrakis‐(4‐chlorophenylthio)‐butatriene (3a) and tetrakis‐(tert‐butylthio)‐butatriene (3b) were synthesized, and their crystal structures were determined. The compound 3a is monoclinic, space group P21/c, a=6.9785(8), b=8.6803(9), c=22.884(2) Å, β=93.887(6), V=1383.0(3) Å, Z=2. The compound 3b is monoclinic, space group P21/n, a=11.0615(6), b=10.8...

The mol­ecule of the title compound, C10H4Cl5NO2S, is not planar. The chloro­phenyl ring and the butadiene group are inclined at an angle of 59.5 (1)°.