Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives

Padalkar, Vikas S.; Borse, Bhushan Nanasaheb; Gupta, Vinod D.; Phatangare, Kiran R.; Patil, Vikas; Umape, Prashant G.; Sekar, Nagaiyan

doi:10.1016/j.arabjc.2011.12.006

Cited by 87 publications

(42 citation statements)

References 17 publications

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“…Benzoxazoles substituted at position 2 are usually synthesized by coupling carboxylic acid derivatives and 2‐aminophenols, frequently with the aid of catalysts, acidic conditions and high temperature . By contrast, many methods use condensation between a 2‐aminophenol and an aldehyde, with subsequent oxidation . In a search for environmentally friendly, milder conditions and easier procedures, we recently developed a synthesis using a double vinylic substitution of 1,1‐bis‐methylsulfanyl‐2‐nitroethylene ( 1 ) and a 2‐aminophenol ( 2 ) …”

Section: Introductionmentioning

confidence: 99%

Benzoxazoles as novel herbicidal agents

Sangi

Meira

Moreira

et al. 2018

Pest Management Science

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Section: Introductionmentioning

confidence: 99%

Benzoxazoles as novel herbicidal agents

Sangi

Meira

Moreira

et al. 2018

Pest Management Science

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“…The increasing incidences of tuberculosis (TB), the number of cases of multi-drug-resistant strains of Mycobacterium tuberculosis (MDR-TB), and infections by nontuberculous mycobacteria (NTM) that are connected with the increase of the number of immunocompromised patients and evolving resistance mycobacterial species to antimycobacterial chemotherapeutics make the discovery of new molecular scaffolds a priority [1–5]. Because of the high profile of M. tuberculosis, the pathogenic role of other NTM in humans was overshadowed for a long time.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimycobacterial and Photosynthesis-Inhibiting Evaluation of 2-[(E)-2-Substituted-ethenyl]-1,3-benzoxazoles

Imramovský

Kozic

Peško

et al. 2014

The Scientific World Journal

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A series of twelve 2-[(E)-2-substituted-ethenyl]-1,3-benzoxazoles was designed. All the synthesized compounds were tested against three mycobacterial strains. The compounds were also evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 2-[(E)-2-(4-Methoxyphenyl)ethenyl]-1,3-benzoxazole, 2-[(E)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1,3-benzoxazole and 2-{(E)-2-[4-(methylsulfanyl)phenyl]ethenyl}-1,3-benzoxazole showed the highest activity against M. tuberculosis, M. kansasii, and M. avium, and they demonstrated significantly higher activity against M. avium and M. kansasii than isoniazid. The PET-inhibiting activity of the most active ortho-substituted compound 2-[(E)-2-(2-methoxyphenyl)ethenyl]-1,3-benzoxazole was IC50 = 76.3 μmol/L, while the PET-inhibiting activity of para-substituted compounds was significantly lower. The site of inhibitory action of tested compounds is situated on the donor side of photosystem II. The structure-activity relationships are discussed.

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“…Condensed heterocyclic systems are of considerable interest not only because of their potential biological activities, but also because of their versatility as synthones in organic transformations (Taylor and Mckillop, 1970;Erian, 1993). The literature survey has revealed that 2-amino benzothiazole and the compounds containing this moiety exhibit excellent biological activity (Sahu et al, 2012;Tomi et al, 2012;Malik et al, 2013;Padalkar et al, 2011;Wang et al, 2011;Solomon et al, 2-Aminobenzothiazolomethyl naphthol derivatives have been reported by Shaabani et al, 2007, with drawbacks such as long reaction time and large quantity of catalyst at 90°C. Kumar et al (2010a, b) have also synthesized the target compounds with drawbacks like higher temperature, no recyclability of catalyst, larger mol% of catalyst, and comparatively long reaction time.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antimicrobial activity of 2-aminobenzothiazolomethyl naphthol derivatives

Sahu

Thavaselvam

et al. 2014

Med Chem Res

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An efficient method is described for the synthesis of 2-aminobenzothiazolomethyl naphthol derivatives by one-pot three-component reaction of aldehydes, 2-naphthol, and 2-amino benzothiazole using triton X-100 as a catalyst in water with good yield. The synthesized compounds have been characterized by IR, 1 H NMR, 13 C NMR, and mass spectra. The synthesized compounds were screened for their antibacterial activity against gram-positive and gram-negative bacteria viz. Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, Bacillus cereus, and Providencia rettegeri and fungal activity against fungal strain such as Aspergillus niger, Aspergillus fumigatus, and Aspergillus flavus. Synthesized compounds exhibited MICs value between 3.25 and 12.5 lg/mL against bacterial strains and 6.25 and 12.5 lg/mL against fungal strains as shown in Tables 4 and 5, respectively. Derivatives 5c and 5h were equipotent activity as ciprofloxacin against E. coli and 5k against P. aeruginosa and B. cereus. Derivatives 5e, 5g, and 5k exhibited excellent antifungal activity against all tested fungal strains. Ciprofloxacin and fluconazole have been used as standard drugs for antibacterial and antifungal activity, respectively.

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Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives

Cited by 87 publications

References 17 publications

Benzoxazoles as novel herbicidal agents

Benzoxazoles as novel herbicidal agents

Synthesis and Antimycobacterial and Photosynthesis-Inhibiting Evaluation of 2-[(E)-2-Substituted-ethenyl]-1,3-benzoxazoles

Synthesis and evaluation of antimicrobial activity of 2-aminobenzothiazolomethyl naphthol derivatives

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