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Journal ArticleDOI

Synthesis of Bioactive 4-Oxo-4H-Chromenes Bearing Heterocyclic Systems from Hydrazonecarbodithioic Acid and Thiocarbohydrazone

12 Aug 2008-Phosphorus Sulfur and Silicon and The Related Elements (Taylor & Francis Group)-Vol. 183, Iss: 9, pp 2139-2160
TL;DR: In this article, the synthesis of 4-oxo-4H-chromene-3-carboxaldehydes with acid hydrazine-carbodithioic acid and/or thiocarbohydrazide has been studied.
Abstract: Condensation 4-oxo-4H-chromene-3-carboxaldehydes (1a,b) with acid hydrazine-carbodithioic acid and/or thiocarbohydrazide afforded hydrazonecarbodithioic acid 2, monothiocarbohydrazone 3a,b and bisthiocarbohydrazone 4, respectively. Heterocyclization of 2–4 via reaction with oxygen, sulfur and/or halogen reagents in different media yielded pyridazinethione 5; 1,3-thiazoles 7; pyrazoles 9–12; 1,2,4-thiadiazoles 8,13,14, and 23; 1,2,4-triazolethiones 15–17; 1,2,4-triazinethiones 18–22; imidazolethione 24 and pyrimidinethione 25 derivatives. Antifungal activity was screened for some the new synthesized compounds. Formulations of all products have been deduced by elemental analysis and spectral data (IR, 1H NMR and Mass spectroscopy).
Citations
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Journal ArticleDOI
TL;DR: In this article, the authors showed that 5,6-diphenyl-3-hydrazino-1,2,4-triazine (1) with bis(methylthio)methylene]malononitrile (2) with benzoyl chloride and sodium pyruvate (3) with acetic anhydride produced pyrazolo[5,4,3-kl]pyrimido[4, 3-d]pyridine 6, which was allowed to react with hydrazine hydrate to give the corresponding hyd

112 citations

Journal ArticleDOI
TL;DR: Some new sulfur-nitrogen heterocyclic systems such as 1, 3-thiazoles, 1,3,4-thiadiazoles and 1, 2, 4-triazoles incorporating acridine and 1 2, 3, 4 -tetrahydroacridine moieties were synthesized via heterocycling of the key intermediate 4-(acridin-9-yl)-1-(1, 2.3, 4t, 4, 4)-thiosemicarbazide as discussed by the authors.
Abstract: Some new sulfur-nitrogen heterocyclic systems such as 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties were synthesized via heterocyclization of the key intermediate 4-(acridin-9-yl)-1-(1,2,3,4-tetrahydroacridin-9-ylcarbonyl)thiosemicarbazide. Structures of the new comp-ounds were established by elemental analyses and spectral data. All the products were also screened in vitro for their antimicrobial activity.

50 citations

Journal ArticleDOI
TL;DR: A new series of 1, 2, 4-triazine derivatives possessing indole nucleus were synthesized with an aim to explore their effect on in vitro growth of microorganisms causing microbial infection and some compounds were found to exhibit better activity with less toxicity than Ciprofloxacin.

42 citations

Journal ArticleDOI
TL;DR: Experiments and computations indicate a three-step reaction including isomerization of diazomethane, a C-C or N-C coupling, and a formal cycloaddition reaction.
Abstract: (Me3Si)2CNN isomerizes upon addition of traces of [Me3Si]+ ions to give (Me3Si)2NNC, which then undergoes an unusual trimerization reaction to give exclusively 4-diazenyl-3-hydrazinylpyrazole. As catalyst the isonitrilium ion, [(Me3Si)2NNC(SiMe3)]+, was identified and fully characterized. Experiments and computations indicate a three-step reaction including isomerization of diazomethane, a C–C or N–C coupling, and a formal cycloaddition reaction. The kinetics and thermodynamics are discussed on the basis of DFT calculations.

40 citations

References
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Journal ArticleDOI
TL;DR: The newly synthesised compounds were screened for their anticancer activity against a panel of 60 cell lines derived from seven cancer types namely, lung, colon, melanoma, renal, ovarian, CNS and leukemia and showed promising anticancer properties.

343 citations

Journal ArticleDOI
TL;DR: By the application of the Vilsmeier-Haack reaction to various o-hydroxyacetophenone derivatives, 4-oxo-4H-1-benzopyran-3-carboxaldehydes were synthesized in one step as discussed by the authors.

175 citations

Journal ArticleDOI
01 Mar 1998-Farmaco
TL;DR: The hereditary bleaching effect on the plastid system of Euglena gracilis, a unique phenomenon of the biological activity of chromone derivatives, is reported and is used for detecting extranuclear mutations.
Abstract: The synthesis of the biologically active novel systems derived from reaction of 3-formylchromones with three types of amino derivatives, 6-R2-2-aminobenzothiazoles, 6-amino-2-R3-thiobenzothiazoles and hydrazide derivatives (derived from cyanoacetic, isonicotine, salicylic and gallic acids) was carried out. The structures of the prepared compounds have been proved by elemental analysis, 1H NMR and IR spectra. Antimicrobial activity was studied against the following microorganisms — bacteria G+ (Staphylococcus aureus 29 58 , Bacillus subtilis 18 66 ), G− (Escherichia coli 326 71 , Pseudomonas aeruginosa); yeasts; Candida albicans, Saccharomyces cerevisiae; moulds; Microsporum gypseum, Aspergillus niger, Scopulariopsis brevicaulis; and against typical and atypical mycobacteria: Mycobacterium tuberculosis (H37Rv), Mycobacterium kansasii (PFG 8), Mycobacterium avium (My 80 72 ), Mycobacterium fortuitum (1021). The hereditary bleaching effect on the plastid system of Euglena gracilis, a unique phenomenon of the biological activity of chromone derivatives, is reported. The bleaching test on E. gracilis is used for detecting extranuclear mutations.

88 citations

Journal ArticleDOI
Nehir Gulerman1, H. N. Dogan1, Sevim Rollas1, C. Johansson1, C. Celik1 
01 Dec 2001-Farmaco
TL;DR: The antibacterial, antifungal and antimycobacterial activities, together with those of known intermediate 1,4-disubstituted thiosemicarbazides, were reported.
Abstract: 5-(4-Pyridinyl)-4-substituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 5-(4-pyridinyl)-4-substituted-3-(benzoylmethyl)thio-4H-1,2,4-triazoles were synthesized. The structures of original nine compounds were confirmed by IR, 1H NMR, mass spectral methods and elemental analysis. The antibacterial, antifungal and antimycobacterial activities, together with those of known intermediate 1,4-disubstituted thiosemicarbazides, were reported.

86 citations

Journal ArticleDOI
TL;DR: Some new isolated and fused heterobicyclic nitrogen systems have been synthesized via treatment of 4-amino-6-styryl-3-thioxo-1, 2,4-triazin-5(2,4H)ones with cyclic and acyclic oxygen and nitrogen compounds as mentioned in this paper.
Abstract: Some new isolated and fused heterobicyclic nitrogen systems such as thiazolidinone, imidazolone, pyrimidinone, quinazolone, as-triazolone, as-triazinones, tetrazino-as-triazines, and the related compounds 3,4-diaminotriazine and sulfa derivatives 2–27 have been synthesized via treatment of 4-amino-6-styryl-3-thioxo-1,2,4-triazin-5(2,4H)ones (1) with cyclic and acyclic oxygen and nitrogen compounds. The structures of the products have been established from their elemental and spectral analyses. Some new compounds exhibited significant anticancer activities, where compounds 11j > 2a > 6 and 11I > 14 > 11k showed a moderate activity toward leukemia, ovarian cancer, and non-small cell lung cancer. The authors are very grateful to Prof. Dr. Johan P. Bader, Chief Antiviral Evaluations Branch and Prof. Dr. V. L. Narayanan, Chief Drug Synthesis, Chemistry Branch National Cancer Institute, Bethesda, Maryland, USA for evalution of the vitro antitumor tests as development program. Thanks also are due to the members ...

60 citations