Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents

Rashid, Mohd; Husain, Asif; Mishra, Ravinesh

doi:10.1016/j.ejmech.2012.04.027

Cited by 143 publications

(81 citation statements)

References 28 publications

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“…Since 1985 benzimidazole containing compounds have been reported as well known anticancer agents. [19][20][21][22][23][24][25] The role of mammalian DNA topoisomerases as molecular targets for anticancer drugs has been recognized. Some benzimidazoles have been reported as topoisomerase inhibitors, e.g.…”

Section: Introductionmentioning

confidence: 99%

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Mohareb

Mohamed²,

Abdallah³

2016

ACSi

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The reaction of ethyl cyanoacetate with o-phenylenediamine gave the 2-cyanomethylbenzo[c]imidazole (1). The latter compound was used as the key starting material to synthesise biologically active heterocyclic derivatives. Thus, the reaction of 1 with cyclohexanone and either of benzaldehyde, 4-methoxybenzaldehyde or 4-chlorobenzaldehyde gave the annulated derivatives 2a-c, respectively. The antitumor evaluations of the newly synthesized products against the three cancer cell lines MCF-7 (breast adeno-carcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) showed that compounds 2b, 6, 11b, 11c, 12b, 16a, 16b and 18a exhibited optimal cytotoxic effect against cancer cell lines, with IC 50 values in the nM range. Bioactive compounds are often toxic to shrimp larvae. Thus, in order to monitor these chemicals in vivo lethality to shrimp larvae (Artemia salina), Brine-Shrimp Lethality Assay was used. Compounds 11b, 12b and 16b showed no toxicity against the tested organisms.

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Section: Introductionmentioning

confidence: 99%

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Mohareb

Mohamed²,

Abdallah³

2016

ACSi

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“…1,2 Benzimidazole ring count a significant heterocyclic pharmacophore in the drug discovery, these compounds which carrying diverse substituents in the structure of benzimidazole are associated with a wide range of biological activities including: antifungal, 3,4,5 anticancer, 6,7,8 antiinflammatory, 9,10 antioxidant, 11,12,13 anti-bacterial, 14,15,16,17 anti-viral, 18,19 anticoagulant, 20 and anti-hypertensive properties. 21 Despite of many attempts to develop and discover new structural type in the search for great and more effective antimicrobials, benzimidazoles still consider as one of the most versatile and significant type of compounds against microbes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Evaluation of some Novel Benzimidazole Derivatives Containing 1,3,4-Thiadiazole Moiety.

Redayan¹,

Ali²,

Mohammed³

2017

Orient. J. Chem

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A series of novel 5-amino-1,3,4-thiadiazole-2-thiol and 1,3,4-thiadiazole-2,5-dithiol derivatives of benzimidazole were synthesized through nucleophilic substitution reaction of 5-substituted-2-(chloromethyl)-1H-benzimidazole, structures of the synthesized compounds were proved by spectral methods of analysis ( FT-IR, 1 H and 13 C NMR ). All the target compounds were screened for their antibacterial activity toward gram-negative (E.coli, P. aeruginosa) and Gram-positive (B. subtilis, S. aureus) bacteria, most of the synthesized derivatives exhibited good to moderate activity toward both Gram-positive (B. subtilis, S. aureus) and Gram-negative (E.coli, P. aeruginosa) bacteria.

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“…Furthermore the 1,3,4-oxadiazole derivatives have some industrial applications in the fields of dyes, photosensitivity electrical materials and liquid crystals [15]. 1,3,4-Oxadiazoles and their derivatives represent an important scaffold that has been found in many natural and synthesized molecules because of their remarkable biological activities [16] as anticancer [17], antifungal [18], antitumor [19], antibacterial [20], antiparasitic [22], anti-HIV [22], anti-infective [23], muscle relaxants [24], antiseptics [25] and cathepsin K inhibitors [26].…”

Section: Introductionmentioning

confidence: 99%

Microwave Synthesis and Antibacterial Activities of Some Imidazolidine Derivatives Containing 1,3,4-Oxadiazole Moiety

Abood¹,

Ali²,

Qabel³

et al. 2018

Asian J. Chem.

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5-(4-Aminophenyl)-2-thiol-1,3,4-oxadiazole (1) was synthesized via the reaction of carbon disulfide with 4-aminobenzoyl hydrazide in presence of potassium hydroxide in absolute ethanol. Compound 1 was converted to the corresponding diazonium salt which was introduced in coupling reaction with alkaline solution of 2-hydroxybenzaldehyde as coupling reagent to give azooxadiazole derivative 2 containing aldehyde group. The resulting aldehyde 2 was then introduced in condensation reactions with the primary aromatic amines including (4-bromoaniline, 4-chloroaniline, 4-nitroaniline, 3-nitroaniline, 4-methoxyaniline and 4-hydroxyaniline) using microwave irradiation technique in absolute ethanol to produce six imine derivatives of 1,3,4-oxadiazole (3a-f), respectively. Treatment of the resulting imines 3a-f with glycine using microwave irradiation in tetrahydrofuran afforded six new imidazolidines 4a-f substituted with 1,3,4-oxadiazole moiety, respectively. in vitro Antibacterial activity of the target compounds were investigated using two types of bacteria, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The results indicated that the newly synthesized imidazolidines (compounds 4d and 4f) showed enhanced activity against Gram-negative bacteria when compared with that of the control drug (gentamycin).

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Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents

Cited by 143 publications

References 28 publications

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

Synthesis, Characterization and Antibacterial Evaluation of some Novel Benzimidazole Derivatives Containing 1,3,4-Thiadiazole Moiety.

Microwave Synthesis and Antibacterial Activities of Some Imidazolidine Derivatives Containing 1,3,4-Oxadiazole Moiety

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