29483-72-5Relevant articles and documents
Anthranilic amide and imidazobenzothiadiazole compounds disrupt: Mycobacterium tuberculosis membrane potential
Smith, Jake,Wescott, Heather,Early, Julie,Mullen, Steven,Guzman, Junitta,Odingo, Joshua,Lamar, Jason,Parish, Tanya
supporting information, p. 934 - 945 (2019/06/27)
A family of compounds typified by an anthranilic amide 1 was identified from a whole-cell screening effort targeted at identifying compounds that disrupt pH homeostasis in Mycobacterium tuberculosis. 1 demonstrated bactericidal activity against non-replicating M. tuberculosis in pH 4.5 buffer (MBC4.5 = 6.3 μM). Exploration of the structure-activity relations failed to simplify the scaffold. The antitubercular activity proved dependent on the lipophilicity and planarity of the molecule and directly correlated with mammalian cytotoxicity. Further studies revealed a pH-dependent correlation between the family's disruption of M. tuberculosis membrane potential and antitubercular activity, with active compounds causing a drop in membrane potential at concentrations below their MBC4.5. A second compound family, identified in the same screening effort and typified by imidazo(4,5-e)(2,1,3)benzothiadiazole 2, provided a contrasting profile. As with 1, structure-activity profiling of 2 (MBC4.5 = 25 μM) failed to minimize the initial scaffold, mammalian cytotoxicity was observed for a majority of the active compounds, and many of the active compounds disrupted M. tuberculosis membrane potential. However, unlike the anthranilic amide compounds, the benzothiadiazole compounds disrupted M. tuberculosis membrane potential primarily at concentrations above the MBC4.5 in a pH-independent fashion. These differences suggest an alternative mechanism of action for the benzothiadiazole compounds. As a result, while the cytotoxicity of the anthranilic amides limits their utility to tool compounds, benzothiadiazole 2 presents an attractive target for more focused SAR exploration.
N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as preparation thereof and use thereof
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Paragraph 0041; 0042; 0043, (2016/10/24)
The invention relates to N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide as well as a preparation thereof and use thereof. A structural formula of the N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide is as shown in the specification. The preparation method comprises the following steps: taking o-nitrobenzoic acid as a starting material, and carrying out amidation to obtain an intermediate 2-nitrobenzamide; then, reducing nitryl into amido by use of iron powder; and finally, enabling the amido to act with the intermediate acyl chloride under the action of triethylamine, thereby acquiring a target compound N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide. The N-(2-pyridyl)-2-(2,4-dimethyl parazole formamido) benzamide has the beneficial effects that the synthesis process is simple; the acquired compound has outstanding bacteriostatic activity on rice sheath blight fungi (Rhizoctorzia solani), and has a bacteriostasis rate of 72.8% on the rice sheath blight fungi under concentration being 1000 ppm.
Benzamides and related inhibitors of factor Xa
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, (2008/06/13)
Novel benzamide compounds including their pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives having activity against mammalian factor Xa are described. Compositions containing such compounds are also described. The comp
