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To expand the potential of nitro-derivatives of benzoic acid as antimycobacterial drugs and explore the effects of various structural features on the activity of these compounds, we have obtained a library of 64 derivatives containing esters and thioesters of benzoates and studied their activity against M. tuberculosis, the stability of the compounds, their activation by mycobacterial enzymes and the potential cytotoxicity against human monocytic THP-1 cell line. Our results showed that the most active compounds are those with an aromatic nitro substitution, with the 3,5-dinitro esters series being the most active. Also, the greater antitubercular activity for the nitro derivatives was shown to be unrelated to their pKa values or hydrolysis rates. Given the conventional relationship between nitro-containing substances and toxicity, one might anticipate that the great antimicrobial activity of nitro compounds would be associated with high toxicity; yet, we have not found such a relationship. The nitrobenzoate scaffold, particularly the 3,5-dinitrobenzoate scaffold, merits further investigation, because it has the potential to generate future antimycobacterial agents with improved activity.<\/jats:p>","DOI":"10.3390\/microorganisms11040969","type":"journal-article","created":{"date-parts":[[2023,4,10]],"date-time":"2023-04-10T05:57:50Z","timestamp":1681106270000},"page":"969","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Nitrobenzoates and Nitrothiobenzoates with Activity against M. tuberculosis"],"prefix":"10.3390","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3865-5913","authenticated-orcid":false,"given":"Jo\u00e3o P.","family":"Pais","sequence":"first","affiliation":[{"name":"Research Institute for Medicines (iMed.UL), Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Olha","family":"Antoniuk","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.UL), Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Raquel","family":"Freire","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.UL), Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9602-1516","authenticated-orcid":false,"given":"David","family":"Pires","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.UL), Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"},{"name":"Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"},{"name":"Center for Interdisciplinary Research in Health, Cat\u00f3lica Medical School, Universidade Cat\u00f3lica Portuguesa, Estrada Oct\u00e1vio Pato, 2635-631 Rio de Mouro, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Em\u00edlia","family":"Valente","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5934-0198","authenticated-orcid":false,"given":"Elsa","family":"Anes","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.UL), Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal"},{"name":"Faculty of Pharmacy, Universidade de Lisboa, Av. 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