Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays

Çoban, Güneş; Zencir, Sevil; Zupkó, István; Réthy, Borbála; Gunes, H. Semih; Topçu, Zeki

doi:10.1016/j.ejmech.2008.06.018

Cited by 48 publications

(31 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The key intermediates were synthesized in accordance with the published procedures. 13) These benzimidazole intermediates reacted with chrysanthemoyl chloride to produce ester compounds. Specifically, where R 2 is -H, intermediates 4 reacted with chrysanthemoyl chloride to give esters 7a-d, 8a-d, or 9a-d, respectively.…”

Section: Chemistrymentioning

confidence: 99%

“…General procedure for preparation of the key intermediates 2-(2-hydroxyphenyl)-1H-benzimidazole, 2-(3-hydroxyphenyl)-1H-benzimidazole, 2-(4-hydroxyphenyl)-1H-benzimidazole and 2-(4-hydroxy-3-methoxyphenyl)-1H-benzimidazole were prepared according to literatures. [12][13][14] Briefly, 0.05 mol of hydroxybenzaldehyde and 0.05 mol of sodium bisulfite were dissolved in 30 mL of ethanol and water, respectively, and then mixed and stirred for 20 min at room temperature. The resulting reaction mixture was filtered, and sodium hydroxy(hydroxyphenyl)-methanesulfonate salt was obtained.…”

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents

Zhang

et al. 2015

J. Pestic. Sci.

View full text Add to dashboard Cite

In the present study, a series of novel benzimidazole derivatives containing chrysanthemum acid moieties was designed and synthesized. Preliminary investigation of biological activity indicated that all of the compounds exhibited lower activity than that of beta-cypermethrin against Plutella xylostella and Lipaphis erysimi; meanwhile, they showed good inhibitory activity against Botrytis cinerea and Sclerotinia sclerotiorum in vitro. The fungicidal activity of compound 8a against B. cinerea was approximately equal to that of thiabendazole and was twice as active against S. sclerotiorum as was thiabendazole. In addition, compound 9e displayed the most potent inhibitory activity against both fungi and was almost twice as potent as thiabendazole.

show abstract

Section: Chemistrymentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents

Zhang

et al. 2015

J. Pestic. Sci.

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4][5][6] Some of the important examples are lansoprazole (anti-ulcer), 7 carbendazim (fungicide), 8 thiabendazole (anthelmintic and fungicide), 9 benperidol (antipsychotic), oxatomide (anti-allergic and anti-asthmatic), 10 etc. Similarly, compounds containing the quinoline nucleus are also known for different therapeutic activities, 11,12 such as chloroquine (antimalarial), 13 chlorquinaldol (antibacterial and antifungal), 14 etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activities of novel n-substituted 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinolines

Chaudhari

Rindhe

2011

JSCS

View full text Add to dashboard Cite

The synthesis of a series of novel 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinoline derivatives is reported. These derivatives were prepared by the condensation of o-phenylenediamine with [(5-chloroquinolin-8-yl)oxy]acetic acid, followed by substitution at nitrogen with different electrophilic reagents in presence of an appropriate base to give a series of nitrogen heterocycles containing the benzimidazole and quinoline nuclei. The structures of the compounds were confirmed based on 1 H-NMR, 13 C--NMR, IR and mass spectral data. Almost all the compounds exhibited promising antibacterial activity against Salmonella typhimurium and Staphylococcus aureus. Some of the compounds showed good antifungal activities against Aspergillus niger but the antifungal activities against Candida albicans were disappointing.

show abstract

“…9 Benzimidazole derivatives also possess a wide spectrum of biological activity such as antibacterial, antitumor and antiviral activities. 10,11 It is interesting to introduce ferrocenesulfonyl moiety into benzimidazole to obtain compounds possessing potential biological activity. Yang et al 12 first reported the synthesis of N-ferrocene-sulfonyl benzimidazoles.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Theoretical Calculation of 1,4‐Bis‐(1‐ferrocenesulfonyl‐2‐benzimidazolyl) Butane

et al. 2011

View full text Add to dashboard Cite

A N,N'-bisferrocenesulfonyl bisbenzimidazole compound 1,4-bis(1-ferrocenesulfonyl-2-benzimidazolyl) butane was prepared. Its crystal structure was determined. The crystal belongs to triclinic with space group P-1 and a＝ 0.87241(13) nm, b＝0.97553(15) nm, c＝1.4120(2) nm, and α＝83.041(2)°, β＝72.454(2)°, γ＝69.732(2)°, the unit cell volume V＝1.0746(3) nm 3 , the molecule number in one unit cell Z＝1, the absorption coefficient µ＝1.191 mm -1 , the calculated density D c ＝1.584 g/cm 3 . The theoretical investigation of the compound as a structure unit was fully optimized by B3LYP/6-31G method in Gaussian 03 package, and the most stable structure of the compound in theory was obtained. The two results were compared. The optimized structure was in accordance with the crystal structure in the main, suggesting that the molecular geometry optimization of the structures was reliable and the calculation method used was reliable. The distribution of atomic charges and the energy, and composition of frontier molecular orbits were analyzed. Thermal analysis indicated that it is stable before melting.

show abstract

Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays

Cited by 48 publications

References 20 publications

Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents

Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents

Synthesis and antimicrobial activities of novel n-substituted 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinolines

Crystal Structure and Theoretical Calculation of 1,4‐Bis‐(1‐ferrocenesulfonyl‐2‐benzimidazolyl) Butane

Contact Info

Product

Resources

About