Synthesis And Microbial Activities of Oxadiazoles, Thia -diazoles And Triazoles Containing 5-Bromo-3-Amino Benzofuran Nucleus From 5- Bromosalicylonitrile

Parameshwarappa, G.; Raga, B.; Khandre, S. Omkar; Sangapure, S. S.

doi:10.1515/hc.2009.15.5.335

Cited by 2 publications

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“…For example, 3‐aminoindole is the core of antiviral compounds against hepatitis B virus and of anti‐proliferative agents and such anti‐mitotic properties were also observed with 3‐aminobenzofuran‐based molecules . Those benzofurans are reported to be involved in potent ischemic cell death inhibitors and anti‐microbiotics as well as in selective fluorescent chemosensors of Zn 2+ and CN − ions …”

Section: Introductionmentioning

confidence: 99%

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Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3‐Amino‐Indoles and ‐Benzofurans

Dagoneau

Kolleth

Quinodoz

et al. 2019

Helvetica Chimica Acta

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Herein, we describe a high yielding approach towards the synthesis of 3-amino-indoles and -benzofurans through 6π-electrocyclization. This was made possible by taking advantage of the high reactivity of keteniminium salts, formed in-situ by treating with triflic anhydride and 2-fluoropyridine amides bearing at the α-position either an aniline or a phenoxy moiety. These mild conditions, on top of furnishing rapidly the 3aminobenzoheteroles, allow the tolerance of various functional groups. Control experiments were carried out to highlight that the keteniminium is, indeed, in most cases, the reactive intermediate and conformational preferences of such species were investigated through a DFT study.

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Section: Introductionmentioning

confidence: 99%

“…The second is the generation of the heterocyclic core followed by in‐situ amination of the latter and the third is the one‐step formation of the 3‐aminobenzoheterole moiety. In this last approach, the main reaction reported is a Thorpe−Ziegler cyclization or variants and actually only a few other methods exist …”

Section: Introductionmentioning

confidence: 99%

Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3‐Amino‐Indoles and ‐Benzofurans

Dagoneau

Kolleth

Quinodoz

et al. 2019

Helvetica Chimica Acta

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“…Key words: acid hydrazides, antibacterial, crystal structure, oxadiazoles, one-pot synthesis, phenoxy acids, urease inhibition Received 7 October 2013, revised 16 December 2013 and accepted for publication 20 January 2014 1,3,4-Oxadiazoles constitute an important class of fivemembered heterocyclic pharmacophores. They have numerous biological applications such as antitumor (1), antibacterial (2), anti-inflammatory (3), anti-HIV (4), anticonvulsant (5), enzyme inhibition (6), NR2B receptors (7), and hypoglycemic (8,9).…”

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confidence: 99%

“…They have numerous biological applications such as antitumor (1), antibacterial (2), anti-inflammatory (3), anti-HIV (4), anticonvulsant (5), enzyme inhibition (6), NR2B receptors (7), and hypoglycemic (8,9). The insecticidal (10,11), fungicidal (12), herbicidal (13), and antimicrobial (4,(14)(15)(16) activities have also been reported for this class of compounds. Besides, being used as core nucleus in liquid crystalline compounds (17), oxadiazoles are also used as fluorescent materials in organic light-emitting diodes (18,19).…”

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confidence: 99%

A Facile One‐Pot Synthesis of 2‐Arylamino‐5‐Aryloxylalkyl‐1,3,4‐Oxadiazoles and Their Urease Inhibition Studies

et al. 2014

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A one-pot method for the synthesis of structural type urease inhibitors, 2-amino-1,3,4-oxadiazoles, was developed. The structures of the compounds were established using spectroanalytical techniques and unambiguously confirmed by single-crystal X-ray analysis of compound 3o. The synthesized compounds were tested against jack beans urease, and most of the compounds (3c, 3g, 3j, 3k, 3n, 3r-3v) were found more active than the standard. The most potent compound (3u) had an IC50 value of 6.03 ± 0.02 μm as compared to the IC50 value of the standard (thiourea; 22.0 ± 1.2 μm). The prominent urease inhibition activity of these compounds may serve as an important finding in the development of less toxic and more potent antiulcer drugs. The compounds were also investigated against four bacterial strains, and some of the compounds (3g and 3r) were found more potent than the standard drug (ciprofloxacin) against all the tested strains. The MIC value for compound 3g was 0.156 μmol/mL against the tested bacterial strains.

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Synthesis And Microbial Activities of Oxadiazoles, Thia -diazoles And Triazoles Containing 5-Bromo-3-Amino Benzofuran Nucleus From 5- Bromosalicylonitrile

Cited by 2 publications

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Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3‐Amino‐Indoles and ‐Benzofurans

Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3‐Amino‐Indoles and ‐Benzofurans

A Facile One‐Pot Synthesis of 2‐Arylamino‐5‐Aryloxylalkyl‐1,3,4‐Oxadiazoles and Their Urease Inhibition Studies

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