Synthesis and tuberculostatic activity of new benzimidazole derivatives

Foks, Henryk; Pancechowska-Ksepko, Danuta; Kuźmierkiewicz, W.; Zwolska, Zofia; Augustynowicz–Kopeć, Ewa; Janowiec, M

doi:10.1007/s10593-006-0135-x

Cited by 31 publications

(7 citation statements)

References 5 publications

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“…A closely related class of compound is the oxadiazolethiones (or thiols) which have become important as intermediates in organic synthesis, [10] in theoretical chemistry…”

Section: Introductionmentioning

confidence: 99%

Powerful Antibacterial Activity of Phenyl‐Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones

et al. 2015

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Seven novel 5‐substituted phenylthiazole oxadiazolethiones: [Me‐PTOT(H)], [MeO‐PTOT(H)], [MeS‐PTOT(H)], [F‐PTOT(H)], [Cl‐PTOT(H)], [Br‐PTOT(H)], and [CF3‐PTOT(H)], {where X‐PTOT(H) = 5‐[2‐(4‐X)thiazol‐4‐yl]‐1,3,4‐oxadiazole‐2(3H)‐thione, 4‐X = C6H4}, were synthesised from their corresponding thioamides. From these seven heteroleptic thiolatobismuth complexes: BiPh(Me‐PTOT)2 6, BiPh(MeO‐PTOT)2 7, BiPh(MeS‐PTOT)2 8, BiPh(F‐PTOT)2 9, BiPh(Cl‐PTOT)2 10, BiPh(Br‐PTOT)2 11 and BiPh(CF3‐PTOT)2 12 were synthesised and characterised. Complexes [10(DMSO)2] and [11(DMSO)2] were structurally characterised using X‐ray diffraction. Evaluation of the antibacterial properties of the thiones and their BiIII complexes against Mycobacterium smegmatis, Staphylococcus aureus (S. aureus), Methicillin‐resistant Staphylococcus aureus (MRSA), Vancomycin‐resistant Enterococcus (VRE), Enterococcus faecalis (E. faecalis) and Escherichia coli (E. coli) showed that all bismuth(III) complexes were highly effective against all the bacteria, as demonstrated by very low MIC values (1.1–2.1 μM). Complexes BiPh(Me‐PTOT)2 6, BiPh(Cl‐PTOT)2 10 and BiPh(Br‐PTOT)2 11, showed best activity against the multi‐drug resistant bacteria VRE and MRSA with an MIC value of 1.0 μM. All these complexes and their corresponding thiones failed to show any prominent activity against M. smegmatis and E. coli, even at high concentrations. These complexes showed little or no toxicity towards mammalian COS‐7 cells at 20 μg/mL.

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“…A closely related class of compound is the oxadiazolethiones (or thiols) which have become important as intermediates in organic synthesis, [10] in theoretical chemistry…”

Section: Introductionmentioning

confidence: 99%

Powerful Antibacterial Activity of Phenyl‐Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones

et al. 2015

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“…Communications have appeared recently on the synthesis of 2-cycloalkyl(aralkyl)benzimidazoles and sulfonylation of the latter with methane-and benzenesulfonyl chlorides [9]. Similar reactions for 2-alkylbenzimidazoles have not been studied.…”

Section: -Alkylbenzimidazoles Have Been Obtained From O-nitroanilinementioning

confidence: 99%

“…Among 2-substituted benzimidazoles are found substances possessing antitumor, hypotensive, spasmolytic, neuroleptic, and antibacterial action [2-6], and also herbicidal, fungicidal, and growth stimulating activity [7,8].Communications have appeared recently on the synthesis of 2-cycloalkyl(aralkyl)benzimidazoles and sulfonylation of the latter with methane-and benzenesulfonyl chlorides [9]. Similar reactions for 2-alkylbenzimidazoles have not been studied.…”

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confidence: 99%

Benzazoles. 3*. Synthesis and arylsulfonylation of 2-substituted benzimidazoles

Abdireimov

Mukhamedov

Aiymbetov

et al. 2010

Chem Heterocycl Comp

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2-Alkylbenzimidazoles have been obtained from o-nitroaniline and aliphatic carboxylic acids by reductive cyclization.Interaction of the former with arenesulfonyl chlorides led to the synthesis of 2-alkyl-1-arylsulfonylbenzimidazoles, the yield of which depended on the structure of the substituent in position 2.The high biological activity and broad spectrum of action of benzimidazole derivatives [2-8] has caused increased interest in them. Among 2-substituted benzimidazoles are found substances possessing antitumor, hypotensive, spasmolytic, neuroleptic, and antibacterial action [2-6], and also herbicidal, fungicidal, and growth stimulating activity [7,8].Communications have appeared recently on the synthesis of 2-cycloalkyl(aralkyl)benzimidazoles and sulfonylation of the latter with methane-and benzenesulfonyl chlorides [9]. Similar reactions for 2-alkylbenzimidazoles have not been studied. Continuing our investigations on the synthesis and conversion of benzazoles [1], in this work we have synthesized 2-alkylbenzimidazoles 2a-e and have studied their interaction with arene sulfonyl chlorides.2-Alkylbenzimidazoles were obtained previously from o-phenylenediamine and the appropriate acids [10]. Compounds 2a-e were synthesized by us from o-nitroaniline (1) and aliphatic acids by reductive cyclization using iron powder and hydrochloric acid. The interaction of products 2a-e with arene sulfonyl chlorides in the presence of triethylamine at room temperature led to 2-alkyl-1-arylsulfonyl benzimidazoles 3a-e and 8a-e (Table 1).It should be noted that with the lengthening of the substituent R the yields of compounds 3a-e and 8a-e were reduced. This is probably explained by the action of steric factors. Substitution in Ar did not have a significant influence on the course of the reaction.

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“…13,14 2-substituted benzimidazoles are pharmacologically more potent antibacterial agents. 15 Presence of amidino moiety on benzimidazole nucleus possess antimicrobial and anti protozoal activity. 16 Aryl or alkyl carboxamide benzimidazole derivatives possess potent antihypertensive activity by inhibiting angiotensine II.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Some New Class of Chromenoimidazole Derivatives as Probable Anti Cancer Agents

2017

RJC

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A new series of compounds with benzimidazole moiety fused pyran ring derivatives were prepared by a simple chemical methodology. Here we have designed and reported a one pot condensation of 6-hydroxy-5-formyl benzimidazole with different N substituted cyano acetamide derivatives to get novel chromeno-benzimidazole molecules which were characterized by different analytical tools and docking study of these compounds against a lung cancer target protein(PDB Id : 3POZ). Most of the compounds exhibited good potency in inhibiting the cancer protein.

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Synthesis and tuberculostatic activity of new benzimidazole derivatives

Abstract: These compounds were transformed into methane-and benzenesulfonamide derivatives. The benzimidazole derivatives obtained were tested in vitro for their tuberculostatic activity. Compounds with good activity (MIC 6.2-25 µg/ml) have been found.

Cited by 31 publications

References 5 publications

Powerful Antibacterial Activity of Phenyl‐Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones

Powerful Antibacterial Activity of Phenyl‐Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones

Benzazoles. 3*. Synthesis and arylsulfonylation of 2-substituted benzimidazoles

Synthesis and Biological Evaluation of Some New Class of Chromenoimidazole Derivatives as Probable Anti Cancer Agents

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