Synthesis, Antibacterial Activity of 2,4-Disubstituted Oxazoles and Thiazoles as Bioisosteres

Kaspady, Mohamed; Venugopala, Katharigatta N.; Raju, Mohana; Rao, Gopal Krishna

doi:10.2174/157018009787158481

Cited by 113 publications

(68 citation statements)

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“…The method is rooted in the principle that microbial cell number increases as the microbial growth proceeds in a log phase of growth which results in increased absorbance of broth medium. 29,30 Three gram-negative (Salmonella typhi, Escherichia coli and Pseudomonas aeruginosa) and two gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus) were included in the study. The organisms were maintained on stock culture agar medium.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis of Some Unique Carbamate Derivatives bearing 2-Furoyl-1-piperazine as Valuable Therapeutic Agents

Abbasi¹,

Hussain²,

Rehman³

et al. 2017

ACSi

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The aim of the research work was to synthesize different biologically active carbamate derivatives bearing 2-furoyl-1-piperazine and having modest toxicity. The synthesis was completed as a multiple sequence. The structural confirmation of all the synthesized compounds was obtained by EI-MS, IR and 1 H-NMR spectral data. The enzyme inhibition and antibacterial potential of the synthesized compounds was evaluated. To find the utility of the prepared compounds as possible therapeutic agents their cytotoxicity was also checked. All the compounds were active against acetylcholinesterase enzyme, especially 12 and 14 showed very good inhibitory potential relative to Eserine, a reference standard. Almost all the compounds showed good activities against both Gram-positive and Gram-negative bacterial strains.

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Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis of Some Unique Carbamate Derivatives bearing 2-Furoyl-1-piperazine as Valuable Therapeutic Agents

Abbasi¹,

Hussain²,

Rehman³

et al. 2017

ACSi

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“…The principle of the method is that as microbial cell population increases during log phase growth, there is an increase in the absorbance of the broth medium (Kaspady et al, 2009;Nafeesa et al, 2015). Ciprofloxacin was used as reference standard.…”

Section: Antibacterial Activity Assaymentioning

confidence: 99%

Synthesis of some novel enzyme inhibitors and antibacterial agents derived from 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol

Sattar

Aziz-Ur-Rehman

Abbasi

et al. 2016

Braz. J. Pharm. Sci.

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Keeping in mind the pharmacological importance of the 1,3,4-oxadiazole moiety, a series of new S-substituted derivatives, 5a-h, of 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol (3) were synthesized. The reaction of p-toluenesulfonyl chloride (a) and ethyl isonipecotate (b) produced ethyl 1-(4-tosyl)piperidin-4-carboxylate (1) which was further transformed into 1-(4-tosyl)piperidin-4-carbohydrazide (2) by hydrazine hydrate in methanol. Compound 2 was refluxed with CS 2 in the presence of KOH to synthesize 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol (3). The desired compounds, 5a-h, were synthesized by stirring 3 with aralkyl halides, 4a-h, in DMF using NaH as an activator. The structures of synthesized compounds were elucidated by 1 H-NMR, IR and EI-MS spectral studies. These compounds were further evaluated for enzyme inhibitory activity against lipoxygenase and alpha-glucosidase, along with antibacterial activity against Gram-negative and Gram-positive bacteria.

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“…The method is based on the principle that microbial cell number increases as the microbial growth proceeds in a log phase of growth which results in increased absorbance of broth medium (Kaspady et al, 2009;Yang et al, 2006).…”

Section: Antibacterial Activitymentioning

confidence: 99%

Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents

Rubab

Abbasi

Aziz-Ur-Rehman

et al. 2015

Braz. J. Pharm. Sci.

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A series of N-substituted 2-{[5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides (8a-w) was synthesized in three steps. The first step involved the sequential conversion of 2-(1H-indol-3-yl) acetic acid (1) to ester (2) followed by hydrazide (3) formation and finally cyclization in the presence of CS 2 and alcoholic KOH yielded 5-(1H-indole-3-yl-methyl)-1,3,4-oxadiazole-2-thiol (4). In the second step, aryl/aralkyl amines (5a-w) were reacted with 2-bromoacetyl bromide (6) in basic medium to yield 2-bromo-N-substituted acetamides (7a-w). In the third step, these electrophiles (7a-w) were reacted with 4 to afford the target compounds (8a-w). Structural elucidation of all the synthesized derivatives was done by 1 H-NMR, IR and EI-MS spectral techniques. Moreover, they were screened for antibacterial and hemolytic activity. Enzyme inhibition activity was well supported by molecular docking results, for example, compound 8q exhibited better inhibitory potential against α-glucosidase, while 8g and 8b exhibited comparatively better inhibition against butyrylcholinesterase and lipoxygenase, respectively. Similarly, compounds 8b and 8c showed very good antibacterial activity against Salmonella typhi, which was very close to that of ciprofloxacin, a standard antibiotic used in this study. 8c and 8l also showed very good antibacterial activity against Staphylococcus aureus as well. Almost all compounds showed very slight hemolytic activity, where 8p exhibited the least. Therefore, the molecules synthesized may have utility as suitable therapeutic agents.sulfanyl}acetamides/antibacterial activity. N-substituted 2-{[5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl} acetmides/hmolytic activity. α-Glicosidase. Butirylcholinesterase. Lipoxygenase.Uma série de acetamidas 2-{[5-(1H-indol-3-ilmetil)-1,3,4-oxadiazol-2-il]sulfanila} N-substituídas (8a-w) foi sintetizada em três fases. A primeira etapa envolveu a conversão sequencial de ácido 2-(1H-indol-3-il) acético (1) a éster (2), seguido por hidrazida (3) e, finalmente, a e ciclização na presença de CS 2 e KOH alcoólico produziu 5-(1H-indol-3-il-metil)-1,3,4-oxadiazole-2-tiol (4). Na segunda etapa, aminas arílicas/ aralquílicas(5a-w) reagiram com brometo de 2-bromoacetila (6 ), em meio básico, para se obter acetamidas 2-bromo-N-substituídas (7a-w). Na terceira etapa, estes eletrófilos (7a-w) reagiram com 4, para se obter os compostos alvo (8a-w). A elucidação estrutural de todos os derivados sintetizados foi realizada por 1 H-NMR, IR e técnicas de espectrometria de EI-MS. Além disso, eles foram submetidos a triagem de atividade antibacteriana e hemolítica. Análise da inibição enzimática foi bem apoiada pelos resultados de docking molecular. Por exemplo, o composto 8q exibiu melhor potencial inibitório contra α-glicosidase,e os compostos 8g e 8b exibiram, comparativamente, melhor inibição contra butirilcolinesterase (BChE) elipoxigenase (LOX), respectivamente. Do mesmo modo os compostos 8b e 8c mostraram excelente potencial antibacteriano contra SalmonellaTyphi...

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Synthesis, Antibacterial Activity of 2,4-Disubstituted Oxazoles and Thiazoles as Bioisosteres

Cited by 113 publications

References 0 publications

Synthesis of Some Unique Carbamate Derivatives bearing 2-Furoyl-1-piperazine as Valuable Therapeutic Agents

Synthesis of Some Unique Carbamate Derivatives bearing 2-Furoyl-1-piperazine as Valuable Therapeutic Agents

Synthesis of some novel enzyme inhibitors and antibacterial agents derived from 5-(1-(4-tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol

Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents

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