2-Ethanethioamide in Heterocyclic Synthesis: Synthesis and Characterization of Several New Pyridine and Fused Azolo- and Azinopyridine Derivatives

Pyridine-2(1H)-thione derivatives 3a,b were synthesized from the reaction of 1-(phenyl-sulfanyl)acetone (1) and cinnnamonitrile derivatives 2a,b. Compounds 3a,b reacted with different halogenated reagents 7a–f to give 2-S-alkylpyridine derivatives 8a–l, which could be, in turn, cyclized into the corresponding thieno[2,3-b]pyridine derivatives 9a–l. Compounds 9d,j reacted with acetic anhydride, formic acid, carbon disulfide, phenyl isothiocyanate, and nitrous acid to yield the corresponding pyrido[3′,2′:4,5]thieno[2,3-d]pyrimidine 12a,b, 15a,b, 17a,b, 20a,b, and pyrido[3′,2′:4,5]thieno[2,3-d][1,2,3]triazinone derivatives 22a,b, respectively.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Synthesis,characterization and biocidal studies of new ferrocenyl thiadiazolo‐triazinone complexes

One‐pot synthesis of ferrocenyl ligand, 1,1′‐bis[1,5‐methyl‐4H‐(1,3,4)‐thiadiazolo(2,3‐c)(1,2,4)triazin‐4‐one]ferrocene was prepared from the reaction of 1,1′‐diacetylferrocene with 4‐amino‐2,3‐dihydro‐6‐methyl‐3‐thioxo[1,2,4]triazin‐5(4H)one. The ligand, L, forms 1:1 complexes with Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) in good yield. Characterization of the ligand and its complexes was carried out using IR, ¹H NMR, magnetic susceptibility as well as elemental analysis. Biocidal activity of the ligand and its complexes were determined against the standard fungal strains of Aspergillus niger, Cladosporium herbarum and Fusarium moniliforme using the paper disc diffusion method; and against bacterial strains of Escherichia coli and Staphylococcus aureus using viable cell counting technique. The results indicated that the complexes are biologically more active than the free ligand. The biocidal activity depends on the metal ion, concentration as well as the tested fungi and bacteria. Copyright © 2006 John Wiley & Sons, Ltd.     

Synthesis and characterization of novel derivatives of triazinone

Triazinone is a kind of heterocyclic compound with potential biological activity. The molecular design, synthesis and optimization of lead compounds are important to the development of insecticides. Six new triazinone derivatives were synthesized and characterized by IR, ¹H-NMR and MS spectra. The mechanism of synthesis of aminotriazinone was discussed. Translated from Huaxue Tongbao (Chemistry), 2006, 69(9): 674–679 (in Chinese)     

Biological studies of newly synthesized ferrocenyl complexes containing triazinone moiety

A new ferrocenyl ligand, 1,1′‐bis[1‐methyl‐5‐phenyl‐4H‐(1,3,4)‐thiadiazolo(2,3‐c)(1,2,4)triazin‐4‐one]ferrocene was prepared from the reaction of 1,1′‐diacetylferrocene with 4‐amino‐2,3‐dihydro‐6‐phenyl‐3‐thioxo[1,2,4]triazin‐5(4H)one. The ligand, L, forms 1:1 complexes with Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) in good yield. Characterization of the ligand and its complexes was carried out using IR, ¹H NMR, magnetic susceptibility as well as elemental analysis. Biological activity of the ligand and its complexes were carried out against Aspergillus niger, Cladosporium herbirum and Fusarium moniliformae using filter paper discs; and against bacterial strains of Escherichia coli, Staphylococcus aureus using viable cell counting technique. The results indicated that the ligand is biologically active whereas the complexes are more active than the ligand. Copyright © 2006 John Wiley & Sons, Ltd.     

Synthesis and Biological Activity Screening of Newly Synthesized Trimethoxyphenyl-Based Analogues as Potential Anticancer Agents

A group of novel trimethoxyphenyl (TMP)-based analogues were synthesized by varying the azalactone ring of 2-(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxybenzylidene)oxazolone 1 and characterized using NMR spectral data as well as elemental microanalyses. All synthesized compounds were screened for their cytotoxic activity utilizing the hepatocellular carcinoma (HepG2) cell line. Compounds 9, 10 and 11 exhibited good cytotoxic potency with IC₅₀ values ranging from 1.38 to 3.21 μM compared to podophyllotoxin (podo) as a reference compound. In addition, compounds 9, 10 and 11 exhibited potent inhibition of β-tubulin polymerization. DNA flow cytometry analysis of compound 9 shows cell cycle disturbance at the G2/M phase and a significant increase in Annexin-V-positive cells compared with the untreated control. Compound 9 was further studied regarding its apoptotic potential in HepG2 cells; it decreased the level of MMP and Bcl-2 as well as boosted the level of p53 and Bax compared with the control HepG2 cells.