Synthesis, characterization, and biological activity of phosphorylated/thiophosphorylated compounds of 2‐substituted benzimidazoles

Pareek, Sonu; Vyas, Sushma; Seth, Gita; Vyas, P. C.

doi:10.1002/hc.20385

Cited by 17 publications

(5 citation statements)

References 8 publications

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“…The reaction of S-(benzoxazolyl-2)phosphorodichloridothioate/phosphorodi-chlor idodithioate with different molar ratio(1:1 and 1:2) of phenol/4-chlorophenol/4-nitrophenol in stoichiometric amounts of triethylamine in dry tetrahydrofurane(THF) has offered a series of the corresponding organophosphate phenoxy derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). A schematic presentation of these reactions is given in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Biological Activity of Organophosphates Phenoxy Derivatives Derived from 2-Mercapto Benzoxazole

Jain

Choudhary

Nagar

et al. 2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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A series of biologically active phenoxy derivatives of 2-substituted benzoxazole organophosphates have been synthesized by the reaction of S-(benzoxazolyl-2)phosphorodichloridothioate/phosphorodichloridodithioate with phenol/4-chlorophenol/4-nitrophenol in 1:1 and 1:2 molar ratio. These compounds have been characterized by elemental analysis, IR, 1 H NMR, and 31 P NMR spectral studies. The antibacterial activity of these 2-substituted benzoxazolephenoxy derivatives has been evaluated against pathogenic bacteria Staphylococcus aureus (+ve) and Escherichia coli (-ve). The antifungal activity of these 2-substituted benzoxazolephenoxy derivatives has been evaluated against pathogenic fungi Aspergillusniger and Fusariumoxysporium. All the compounds were found to have moderate antibacterial and antifungal activity.

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Section: Resultsmentioning

confidence: 99%

“…These organic groups affect the strength of biocidal activity. These compounds are well known for their broad spectrum biocidal activities [1][2][3][4][5] . These are used as insecticides, agricultural and horticultural pesticides, and veterinary medicines [6][7][8] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of Organophosphates Phenoxy Derivatives Derived from 2-Mercapto Benzoxazole

Jain

Choudhary

Nagar

et al. 2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…In the spectra of 2-(o-aminophenyl) benzimidazole (A), signals at d 6.4 and d 8.25 ppm were appeared corresponding to free amino and imidazolyl protons respectively. 33,35 The aromatic protons of various environments present in all compounds appeared as multiplets in the range of d 6.84-8.81 ppm.…”

Section: Chemistrymentioning

confidence: 96%

Synthesis and antimicrobial activities of a new class of 6-arylbenzimidazo[1,2-c]quinazolines

Rohini¹,

Shanker²,

Reddy³

et al. 2010

J. Braz. Chem. Soc.

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Uma série de compostos 6-arilbenzimidazo[1,2-c]quinazolina (11)(12)(13)(14)(15)(16)(17)(18)(19)(20) foram sintetizados pela condensação do 2-(o-aminofenil)benzimidazol com diferentes arilaldeídos seguida pela ciclização oxidativa dos 2-o-arilidenoaminofenilbenzimidazol (1-10). Todos os produtos foram caracterizados por espectroscopia no infravermelho (IR), ressonância magnética nuclear de prótons e de carbono, (RMN 1 H e RNN

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“…It is known that benzimidazoles are readily prepared by the reaction of carboxylic acids with orthophenylenediamines [4][5][6][7][8] when heating in the acidic medium like polyphosphoric acid. The reaction of 5methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid 1a [9] with ortho-pnenylediamine 2a was carried out in the polyphosphoric acid medium for 5 h at 190°С when heating, but the desired 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one was not isolated after this procedure.…”

Section: синтез и алкилирование 6-(1h-бензимидазол-2-ил)-5-метилтиеноmentioning

confidence: 99%

Synthesis and alkylation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones

Vlasov

Kovalenko

Chernykh

et al. 2015

J. org. pharm. chem.

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The one-step method for preparation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones by interaction of 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid with ortho-pnenylediamines using 1,1'-carbonyldiimidazole as a coupling-reagent has been developed. The procedure proposed allows to obtain easily the target products using common reagents and solvents; and it also requires the simple isolation methods. The selectivity of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one interaction with benzyl chlorides in DMF-К 2 СО 3 conditions has been studied using the NOESY spectroscopic method and alternative synthetic approaches; it has been determined that the reaction occurs at position 3 of the thieno[2,3-d] pyrimidine system. The study of the antimicrobial activity by the agar diffusion method for the compounds obtained has shown that 6-(1H-benzimidazol-2-yl)-3-benzyl-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones reveal the antimicrobial activity against the strains of Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa; while the compound with unsubstituted position 3 appeared to be inactive against these strains of microorganisms. However, this compound exhibited the higher inhibitory activity against the Candida albicans fungi.

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Synthesis, characterization, and biological activity of phosphorylated/thiophosphorylated compounds of 2‐substituted benzimidazoles

Abstract: A series of phosphorylated and thio-

Cited by 17 publications

References 8 publications

Synthesis and Biological Activity of Organophosphates Phenoxy Derivatives Derived from 2-Mercapto Benzoxazole

Synthesis and Biological Activity of Organophosphates Phenoxy Derivatives Derived from 2-Mercapto Benzoxazole

Synthesis and antimicrobial activities of a new class of 6-arylbenzimidazo[1,2-c]quinazolines

Synthesis and alkylation of 6-(1H-benzimidazol-2-yl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-ones

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