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Design,Synthesis of 3-(5-Substituted Phenyl-[1,3,4]oxadiazol-2-yl)-1H-indole and Its Microbial Activity |
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| Authors: | Manohar D Suryawanshi Ganesh D Suryawanshi Pravin C Mhaske Dnyaneshwar G Karpe Komal R Kamble Sagar J Rode Vilas A Sudrik Shamrao P Lawande |
| Institution: | 1. Department of Chemistry, Shri Chhatrapati Shivaji Mahavidyalaya, 413701 Shrigonda, Ahmednagar (M. S.), India;2. Department of Chemistry, Dada Patil Mahavidyalaya, 414402 Karjat, Ahmednagar (M.S.), India
Contribution: Methodology (supporting);3. Department of Chemistry, Sir Parshurambhau College, 411030 Pune (M.S.), India Contribution: Conceptualization (supporting);4. Department of Chemistry, Shri Chhatrapati Shivaji Mahavidyalaya, 413701 Shrigonda, Ahmednagar (M. S.), India Contribution: Conceptualization (supporting);5. Department of Chemistry, Shri Chhatrapati Shivaji Mahavidyalaya, 413701 Shrigonda, Ahmednagar (M. S.), India Contribution: Software (equal);6. Department of Chemistry, Dada Patil Mahavidyalaya, 414402 Karjat, Ahmednagar (M.S.), India Contribution: Resources (supporting);7. Department of Chemistry, Shri Chhatrapati Shivaji Mahavidyalaya, 413701 Shrigonda, Ahmednagar (M. S.), India Contribution: Methodology (supporting);8. Department of Chemistry, Shri Chhatrapati Shivaji Mahavidyalaya, 413701 Shrigonda, Ahmednagar (M. S.), India Contribution: Conceptualization (equal) |
| Abstract: | Fischer indole synthesis of indole by using phenyl-hydrazine and acetaldehyde resulted 1H-Indole while phenyl-hydrazine reacted with malonaldehyde gives 1H-Indole-3-carbaldehyde. Also Vilsmeier-Haack formylation of 1H-Indole gives 1H-Indole-3-carbaldehyde. 1H-Indole-3-carbaldehyde were oxidized to form 1H-Indole-3-carboxylic acid. 1H-Indole reacted with excess of BuLi at −78 °C using dry ice also gives 1H-Indole-3-carboxylic acid. Obtained 1H-Indole-3-carboxylic acid was converted to ester and ester in to acid hydrazide. Finally 1H-Indole-3-carboxylic acid hydrazide reacted with substituted carboxylic acid gives microbial active indole substituted oxadiazoles. Synthesized compounds 9a – j showing promising in vitro anti microbial activities against S. aureus bacteria compared with Streptomycin. Compound 9a , 9f and 9g showing activities against E. coli compared with standards. Compound 9a and 9f are found potent active against B. subtilis compared with reference standard while compound 9a , 9c and 9j active against S. typhi. |
| Keywords: | indole oxadiazole microbial activity Fischer indole synthesis Vilsmeier-Haack formylation |