New Heterocyclic Compounds from 1,2,4-triazoles Class with Potential Cytotoxic Activity

2017 ◽  
Vol 68 (11) ◽  
pp. 2503-2508 ◽  
Author(s):  
Laura Ileana Socea ◽  
Stefania Felicia Barbuceanu ◽  
Bogdan Socea ◽  
Constantin Draghici ◽  
Theodora Venera Apostol ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Cytotoxic Activity ◽  
Spectral Data ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Cytotoxic Effect ◽  
13C Nmr Spectroscopy ◽  
New Compounds

Acylhydrazinecarbothioamides (2a,b) were synthesized by addition of 2-(5H-dibenzo[a,d][7]annulen-5-yl)acetohydrazide to different isothiocyanates. The new 1,2,4-triazol-3-thioles (3a,b) were synthesized by cyclization of new 2- acylhydrazinecarbothioamides (3a,b) in basic media. Alkylation of 1,2,4-triazole-3-thiols (3a-c) with ethyl bromide gave only S-substituted derivatives (4a-c). The structures of the synthesized compounds have been established on spectral data (IR, 1H-NMR and 13C-NMR spectroscopy) and elemental analysis. The cytotoxic effect of new compounds was evaluated using two alternative models on plant and invertebrate organisms.

scholarly journals Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2793 ◽  
Author(s):  
Ameen Abu-Hashem
Keyword(s):  
Antimicrobial Activity ◽  
Growth Inhibition ◽  
Spectral Data ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Bacteria And Fungi ◽  
New Compounds

Substituted-6-methyl-1-thioxo-1,2-dihydro-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (5a,b) were synthesized from condensation of visnagenone (2a) or khellinone (2b) with 6-amino-thiouracil (3) in dimethylformamide or refluxing of (4a) or (4b) in dimethylformamide. Hence, compounds (5a,b) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (6a,b), furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazolinone (7a,b), substituted-benzylidene-furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazoline-3,5-dione (8a–f), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (9a,b), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (10a,b), 2-(oxo or thioxo)-pyrimidine-furo[3,2-g]pyrimido[1,6-a]quinazolinone (11a–d), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (12a,b), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (13a,b) and 6-methyl-1-((piperazine) or morpholino)-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (14a–d). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, 1H-NMR, 13C-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines 8a–f and 11a–d displayed results excellent for growth inhibition of bacteria and fungi.

scholarly journals Synthesis some 4-substituted 9,10-anthraquinones

2020 ◽  
Vol 8 (1) ◽  
pp. 58-65
Author(s):  
Vasyl Shupeniuk ◽  
Tetyana Taras ◽  
Oksana Sabadakh ◽  
Eugene Luchkevich ◽  
Yurii Kornii
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Analysis Data ◽  
Elemental Analysis Data ◽  
Ullmann Coupling

New 4-substituted 9,10-anthraquinones (6 compouds) with amino derivations fragments were synthesized through the substitution of the bromaminic acid by amines using the Ullmann coupling reaction. The structures of the synthesized compounds were determined using LC-MS, 1H NMR, 13C NMR spectroscopy, and elemental analysis data.

New heterocyclic compounds from 1,2,4-trizoles and 1,3,4-oxadiazoles class containing 5H-dibenzo[a,d][7]annulene moiety

2018 ◽  
Vol 68 (12) ◽  
pp. 2761-2764
Author(s):  
Laura Ileana Socea ◽  
Stefania Felicia Barbuceanu ◽  
Constantin Draghici ◽  
George Mihai Nitulescu ◽  
Gabriel Saramet ◽  
...  
Keyword(s):  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Alkaline Media ◽  
Mercury Oxide ◽  
New Compounds

In this paper we present the synthesis of the new heterocyclic compounds with 5H-dibenzo[a,d][7]annulene moiety obtained by cyclization of 2-acylhydrazinecarbothioamides (2a,b). The acylhydrazinecarbothioamides were obtained by treating 2-(5H-dibenzo[a,d][7]annulen-5-yl)acetohydrazide (1) with 2,5-difluorophenyl or 3-bromophenyl isothiocyanates. 2-Amino-1,3,4-oxadiazoles (3a,b) were synthesized by cyclization of 2- acylhydrazinecarbothioamides in the presence of mercury oxide. The new 1,2,4-triazole-3-thioles (4a,b) were synthesized by cyclization, in alkaline media, of the corresponding acylhydrazinecarbothioamide. The structures of the new compounds synthesized were investigated by 1H-NMR, 13C-NMR, IR and elemental analysis.

Syntheses and Characterization of Two New 4,4’-Bithiazole d10 Complexes, Structural Characterization of M(DABTZ)2(CH3COO)](ClO4) · 2H2O (M = Zn, Cd)

2005 ◽  
Vol 60 (9) ◽  
pp. 951-954 ◽  
Author(s):  
Jafar Abedini ◽  
Ali Morsali
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Structural Characterization ◽  
13C Nmr Spectroscopy ◽  
Acetate Anion ◽  
Aromatic Rings ◽  
Π Stacking Interaction

New zinc(II) and cadmium(II) complexes of the 2,2’-diamino-4,4’-bithiazole (DABTZ) ligand, [M(DABTZ)2(CH3COO)](ClO4), have been synthesized and characterized by elemental analysis, IR, 1H NMR and 13C NMR spectroscopy. The structural characterization of the Cd(DABTZ)2(CH3COO)](ClO4) · 2H2O complex shows the complex to be a monomer and the Cd atom to be coordinated by four nitrogen atoms of the “DABTZ” ligands and two oxygen atoms of the acetate anion. There is an edge-to-edge π-π stacking interaction between the parallel aromatic rings.

Synthesis and Spectral Characterization of New S-Alkylated 1,2,4-Triazoles as Potential Biological Agents

2017 ◽  
Vol 68 (10) ◽  
pp. 2436-2439
Author(s):  
Stefania Felicia Barbuceanu ◽  
Laura Ileana Socea ◽  
Constantin Draghici ◽  
Elena Mihaela Pahontu ◽  
Theodora Venera Apostol ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Spectral Data ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Ethyl Bromide ◽  
Spectral Characterization ◽  
Basic Medium ◽  
Phenacyl Bromide

In the work we presented the behavior of 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(n-propyl)-2H-1,2,4-triazole-3(4H)-thiones (X= Cl or Br) with some alkylation agents. Thus, new S-alkylated 1,2,4-triazole derivatives were synthesized by reaction of the corresponding 1,2,4-triazole-3-thione derivatives with different �-halogenated compounds (ethyl bromide, ethyl chloroacetate or phenacyl bromide), in basic medium. The structures of synthesized compounds were elucidated by spectral data (1H-NMR, 13C-NMR, mass spectrometry) and elemental analysis.

scholarly journals Secondary metabolites of three endemic Centaurea L. species

2014 ◽  
Vol 79 (11) ◽  
pp. 1355-1362 ◽  
Author(s):  
Vele Tesevic ◽  
Ivana Aljancic ◽  
Slobodan Milosavljevic ◽  
Vlatka Vajs ◽  
Iris Djordjevic ◽  
...  
Keyword(s):  
Quantitative Analysis ◽  
Nmr Spectroscopy ◽  
Secondary Metabolites ◽  
Sesquiterpene Lactone ◽  
1H Nmr ◽  
13C Nmr ◽  
1H Nmr Spectroscopy ◽  
13C Nmr Spectroscopy ◽  
Esi Ms ◽  
Aerial Parts

The aerial parts of three endemic Centaurea L. species, namely C. tomorosii Micevski, C. soskae Hayek and C. galicicae Micevski, afforded sesquiterpene lactone cnicin (1) and seven flavonoids: apigenin (2), isokaempferide (3), hispidulin (4), eupatorin (5), cirsimaritin (6), santaflavone (7) and salvigenin (8). The structures of the isolated compounds were determined by UV, 1H NMR and 13C NMR spectroscopy and HR-ESI-MS spectrometry. 1H NMR spectroscopy was used as a method for quantitative analysis of sesquiterpene lactone cnicin.

scholarly journals Cytotoxic and antimicrobial activities of two new synthetic 2'-oxygenated flavones reported from andrographis viscosula

2007 ◽  
Vol 72 (4) ◽  
pp. 321-329 ◽  
Author(s):  
Sohel Mostahar ◽  
Sayed Alam ◽  
Azizul Islam
Keyword(s):  
Spectral Data ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Brine Shrimp ◽  
Antimicrobial Activities ◽  
Good Activity ◽  
Biocidal Activity ◽  
Fungal Strains ◽  
Bacteria And Fungi

Two new 2'-oxygenated flavones have been synthesized via chalcone precursors and the biocidal activity of these two flavones, along with the corresponding chalcones against microbes (bacteria and fungi) and brine shrimp nauplii were investigated. Both the flavones (compounds 6 and 7) and their corresponding chalcones (compounds 4 and 5) showed good activity against all the tested bacterial and fungal strains. The LC50 values of compounds 4-7 were found to be 2.31, 0.94, 1.39 and 0.58 ?gmL -1, respectively. The synthesized compounds were characterized using UV-Vis, IR, 1H-NMR and 13C-NMR spectral data, together with elemental analysis. .

scholarly journals Reaction of substituted 6-oxocyclohexane- 1,3-dicarboxamides with hydroxylamine

2020 ◽  
Vol 63 (9) ◽  
pp. 31-34
Author(s):  
Natalia V. Nosova ◽  
◽  
Daria D. Lezhnina ◽  
Daria D. Rubtsova ◽  
Vladimir L. Gein ◽  
...  
Keyword(s):  
Carbon Atom ◽  
1H Nmr ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Positive Charge ◽  
Hydroxylamine Hydrochloride ◽  
13C Nmr Spectroscopy ◽  
Amide Group ◽  
New Compounds ◽  
Proton Singlet

Functionalized cyclohexanones are multifunctional highly reactive available substrates. They are convenient for the synthesis of new compounds, including practically significant ones. The presence of a 1,3-dicarbonyl fragment in their composition makes it possible to obtain various heterocyclic systems in reactions with binucleophilic reagents: indazoles, benzisoxazoles, and diazepines. The interaction of cyclohexanones functionalized with acetyl or alkoxycarbonyl substituents with hydroxylamine was previously studied. It was shown that, depending on the nature of the substituents, the reaction can proceed with the formation of the corresponding oximes, or give products of heterocyclization – benzisoxazoles. The interaction of cyclohexanones containing amide groups in an alicycle with hydroxylamine has not been studied. We studied the reaction of unsubstituted 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxamides with hydroxylamine hydrochloride in the presence of an equivalent amount of alkali. When boiling in ethanol in the absence of a catalyst, new 2-aryl-4-hydroxy-6-(hydroxyimino)-4-methylcyclohexane-1,3-dicarboxamides were obtained. Cyclization with the formation of benzisoxazoles does not occur in this case due to a lower positive charge on the carbon atom of the amide group compared to the carbon atom of the acetyl or alkoxycarbonyl groups. The structure of the synthesized compounds was established based on the data of IR, 1H NMR and 13C NMR spectroscopy. The IR spectra of the obtained oximes contain bands of valence vibrations of the OH, NH, and CON groups. The 1H NMR spectra contain four NH-proton singlets of two amide groups, the proton singlet =N-OH group. The 13C NMR spectra of solutions of compounds contain signals of two carbon atoms of amide groups and a carbon atom of the C=N-OH group, which fully confirm the assumed structure.

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