Synthesis and antibacterial activity of 4-substituted benzoic acid derivatives

Name: Nipawan Pongprom

Organization : Ubon Ratchathani University. Faculty of Science

Name: Kittaporn Sinsub

Organization : Ubon Ratchathani University. Faculty of Science

Name: Siriluk Buphasiri

Organization : Ubon Ratchathani University. Faculty of Science

Name: Sirirat Jirarotjanakul

Organization : Ubon Ratchathani University. Faculty of Science

Name: Pitchayaporn Suwannakood

Organization : Ubon Ratchathani University. Faculty of Science

Email : nipawan.p@ubu.ac.th

LCSH: Benzoic acid -- Synthesis

LCSH: Antibacterial agents

Abstract: Recently, 3-(N-substituted glycinamido)benzoic acid (2a) and 3-substituted benzoic acid derivatives 2b have been developed as leads for tuberculosis therapy. In this work, we synthesized a series of novel 4-substituted benzoic acid derivatives (3) and ester (4) with an aim to optimize the lead molecule. The synthetic pathway started with 4-methylbenzoic acid which underwent bromination to give 4-(bromomethyl)benzoic acid (75%). Substitution reaction at benzylic position with methanol, phenol and aniline led to a series of 4-substituted benzoic acid derivatives (3). Esterification of the obtained benzoic acid derivatives gave 3 ester products (4). The newly synthesized compounds 3 4, and 5 were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Salmonella enterica typhi and Escherichia coli. The results showed that acid 3a, 3b and 5 exhibited the antibacterial activity against Staphylococcus aureus with minimal inhibitory concentration of 25, 12.5 and 6.25 mg/mL, respectively. While, acid 3a showed highest antibacterial effect against Salmonella enterica typhi with minimal inhibitory concentration of 50 mg/mL. Ester derivatives 4 showed low anti-bacterial activity. Therefore, acid derivative (3) showed higher antibacterial activity than ester (4). This result is useful information for further study on structure modification of this series of compounds

King Mongkut's University of Technology North Bangkok. Central Library

Address: BANGKOK

Email: library@kmutnb.ac.th

Created: 2022

Modified: 2022-11-24

Issued: 2022-11-24

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BibliograpyCitation : In King Mongkut's Institute of Technology Ladkrabang. Pure and Applied Chemistry International Conference (PACCON 2022) (pp.783-786). Bangkok : King Mongkut's Institute of Technology Ladkrabang

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