- Transition metal complexes of asymmetrical aroyl-hydrazone ligand: Syntheses, structures, DNA binding and cleavage studies
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Syntheses and crystal structures of aroyl-hydrazone ligands and their transition metal complexes (E)-N′-(2-hydroxybenzylidene)-1-methyl-4-nitro- 1H-pyrrole-2-carbohydrazide (H21), [CuII(H1)Cl] (2), [FeIII(H1)Cl2
- Wang, Jing-Lin,Zhao, Ya-Qin,Yang, Bin-Sheng
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- Syntheses of substituted 1-methyl-2-(1,3,4-thiadiazol-2-yl)-4-nitropyrroles and 1-methyl-2-(1,3,4-oxadiazol-2-yl)-4-nitropyrroles
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Starting from readily available ethyl-4-nitropyrrole-2-carboxylate (1), substituted 1-methyl-2-(1,3,4-thiadiazel-2-yl)-4-nitropyrroles and 1-methyl-2-(1,3,4-oxadiazol-2-yl)-4-nitropyrroles were prepared. The reaction of 1 with diazemethane gave ethyl 1-methyl-4-nitropyrrole-2-carboxylate (2). Reaction of compound 2 with hydrazine hydrate afforded the corresponding hydrazide 3. The reaction of 3 with formic acid yielded 1-(1-methyl-4-nitropyrrole-2-carboxyl)-2-(formyl)hydrazine (7). Refluxing of the latter with phosphorus pentasulfide in xylene yielded compound 6 in 40% yield. Reaction of compound 7 with phosphorus pentoxide afforded compound 9. Reaction of compound 3 with 1,1'-carboxyldiimidazole in the presence of triethylamine yielded 2-(1-methyl-4-nitro-2-pyrrolyl)-1,3,4-oxadiazoline-4(H)-5-one (11). Refluxing compound 3 with cyanogen bromide in methanol gave compound 12. Compound 13 could be obtained through the reaction of compound 3 with carbon disulfide in basic medium. Alkylation of compound 13 afforded the corresponding alkylthio derivative 14. Reaction of 1-methyl-4-nitropyrrole-2-carboxylic acid (15) with thiosemicarbazide and phosphorus oxychloride gave 2-amino-5-(1-methyl-4-nitro-2-pyrrolyl)-1,3,4-thiadiazole (16). Sandmeyer reaction of compound 16 yielded 2-chloro-5-(1-methyl-4-nitro-2-pyrrolyl)-1,3,4-thiadiazole (17). Refluxing of the latter with thiourea afforded 2-(1-methyl-4-nitro-2-pyrrolyl)-1,3,4-thiadiazotine-4(H)-5-thione (18). Alkylation of compound 18 gave the corresponding alkylthio derivative 19. Oxidation of the latter with hydrogen poroxide in acetic acid yielded 2-(1-methyl-4-nitro-2-pyrrolyl)-5-methylsulfonyl-1,3,4-thiadiazole (20).
- Firoozi,Javidnia,Kamali,Fooladi,Foroumadi,Shafiee
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- A novel class of oligomeric and polymeric d10 metal complexes of asymmetrical N-heterocyclic ligand with strong π-stacking and hydrogen bonding: Syntheses, structures, and photoluminescence
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A novel asymmetric N-heterocyclic ligand, 1·H2O [1 = (E)-1-methyl-4-nitro-N′-(pyridin-2-ylmethylene)-1H-pyrrole-2- carbohydrazide], was generated by a facile route, and some closed shell metal complexes of the ligand were also synthesized. These complexes include [Zn(1)Cl2] (2), [Cd(1)(μ-Cl)2]n (3), [Hg(1)Cl2] (4) and [K(μ-1)(μ-NO3)]n (5), which were characterized by X-ray crystallography, IR and 1H-NMR spectroscopy, and elemental analyses. The structural studies indicate that ligand 1, with its different conformations and new coordination modes, is an important building block for designing and constructing supramolecular structures via π...π stacking, hydrogen bonding, Cl...Cl and d10-d10 interactions. These interactions not only reinforce the stability of structures, but also correlate with the physical properties of complexes. The UV and fluorescence spectral properties were investigated in solution. The titration experiments by d10 metal ions imply that ligand 1 forms stable complexes at a 1:1 ratio and exhibits enhanced fluorescence. Moreover, compared with the solution fluorescence spectra, the solid-state spectra show more significant red-shifts, suggesting that complexes 2-4 have possible applications as light emission materials. This journal is The Royal Society of Chemistry.
- Jing-Lin, Wang,Bin, Liu,Bin-Sheng, Yang
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- Synthesis of novel 4-nitropyrrole-based semicarbazide and thiosemicarbazide hybrids with antimicrobial and anti-tubercular activity
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We report the synthesis and screening of forty novel 4-nitropyrrole- semicarbazide conjugates inspired from the reported bio-potential of bromopyrrole alkaloids and semicarbazide derivatives for antimicrobial activity. Herein, hybrids 5k-5o, 5r, 5s and 5t
- Rane, Rajesh A.,Naphade, Shital S.,Bangalore, Pavan Kumar,Palkar, Mahesh B.,Shaikh, Mahamadhanif S.,Karpoormath, Rajshekhar
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p. 3079 - 3083
(2014/06/24)
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- Synthesis of novel 4-nitropyrrole-based semicarbazide and thiosemicarbazide hybrids with antimicrobial and anti-tubercular activity
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We report the synthesis and screening of forty novel 4-nitropyrrole-semicarbazide conjugates inspired from the reported bio-potential of bromopyrrole alkaloids and semicarbazide derivatives for antimicrobial activity. Herein, hybrids 5k-5o, 5r, 5s and 5t
- Rane, Rajesh A.,Naphade, Shital S.,Bangalore, Pavan Kumar,Palkar, Mahesh B.,Shaikh, Mahamadhanif S.,Karpoormath, Rajshekhar
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p. 3079 - 3083
(2015/02/19)
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- Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents
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We report synthesis and antimicrobial evaluation of 42 novel 4-nitropyrrole-based 1,3,4-oxadiazoles. The synthesized molecules were evaluated for anti-bacterial, anti-fungal and anti-tubercular activities. Promisingly, most of the compounds showed equal o
- Rane, Rajesh A.,Bangalore, Pavankumar,Borhade, Sheetal D.,Khandare, Preeti K.
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