N-(bromomethyl)pyrazine-2-carboxamide (4a): white crystal; 1H NMR (CDCl3, 300 MHz): δ = 9.96 (1H, s, pyrazine-H), 9.38 (1H, s, –NH–), 9.10 (1H, dd, J = 8.0 Hz, pyrazine-H), 8.89 (1H, dd, J = 8.0 Hz, pyrazine-H), 4.97 (2H, s, J = 6.4 Hz, –CH2–); 13C NMR (CDCl3, 75 MHz): δ = 161.0 (C=O), 146.0, 145.0, 144.7, 144.6 (pyrazine-C), 45.4 (CH2); HRESIMS m/z (pos): 216.0376 C6H6N3OBr (calcd. for C8H10N3OBr: C, 39.37; H, 4.13; N, 17.22; Br, 32.74. This synthetic route (Figure 2) was simple, and the yield was higher (79.6%–91.2%). Vol D —0.57 to 0.74 L per kg {23} {24} {25}. 252.1045); Anal. Found: C, 59.99; H, 7.31; N, 25.43. The pyrazinamide has good antibacterial effect, but there are side effects, and the main side effect is to cause liver damage. 248.1637); Anal. The reaction liquid was magnetically stirred, and the reaction lasted 12 h under refluxing. The modified roche medium was used for bacteriostatic experiment, and the MH agar culture medium was used for the experiment of minimal inhibitory concentration (MIC). When pyrazinamide gets into M. tuberculosis bacteria in vivo, the pyrazinoic acid metabolite achieves the bacteriostatic effect. Latent TB was usually used as a single drug, while active TB was most appropriate to take several drugs at the same time for reducing the risk of drug-resistant bacteria8,9. Found: C, 52.35; H, 6.40; N, 22.18; S, 12.72%. We use cookies to help provide and enhance our service and tailor content and ads. N-(2-(piperazin-1-yl)ethyl)pyrazine-2-carboxamide (1e): white crystal; yield 90.4%; m.p. The general method was used to synthesise compounds 4b–4c. N-(2-morpholinoethyl)pyrazine-2-carboxamide (1f): white crystal; yield 91.2%; m.p. The results of biological activity experiment are shown in Table 1. The crude product was recrystallised with toluene, filtered, and dried, respectively. N-(piperidin-1-ylmethyl)pyrazine-2-carboxamide (1a): white crystal; yield 86.2%; m.p. N-(3-morpholinopropyl)pyrazine-2-carboxamide (1j): white crystal; yield 87.3%; m.p. Calcd. The standard strains were dissolved in sterile distilled water, and the bacteria liquid concentration was adjusted to 103 CFU/mL. 204–205 °C; 1H NMR (CDCl3, 300 MHz): δ = 9.96 (1H, s, pyrazine-H), 9.10 (1H, dd, J = 7.5 Hz, pyrazine-H), 8.98 (1H, s, –NH–), 8.89 (1H, dd, J = 7.5 Hz, pyrazine-H), 3.18 (2H, s, J = 5.8 Hz, N–CH2–), 2.42 (4H, m, –CH2–), 2.36 (2H, s, –CH2–), 1.73 (2H, s, –CH2–), 1.49 (4H, m, –CH2–), 1.37 (2H, m, –CH2–); 13C NMR(CDCl3, 75 MHz): δ = 160.7 (C=O), 146.6, 145.0, 144.7, 144.6 (pyrazine-C), 57.1 (CH2, N–CH2), 40.4, 39.7, 27.0, 25.9, 24.5 (CH2, CH2–CH2); HRESIMS m/z (pos): 248.3300 C13H20N4O (calcd. Calcd. The target compounds were synthesised using pyrazinecarboxylic acid as the starting material by acylation, amidation, and alkylation, respectively. Tuberculosis (TB) is a common and fatal chronic infectious disease, and it is easy to occur in young people. Copyright © 2006 Elsevier Ltd. All rights reserved. It indicated that the length of alkyl chain did not obviously affect the reaction yield, but the six-member ring type more obviously influenced the yield. Pyrazinamide is widely distributed to most fluids and tissues, including liver, lungs, kidneys, and bile. Table 1. Figure 2. The modified roche medium was used for the bacteriostatic experiment, and the MH agar was used for the minimum bacteriostatic concentration experiment. Found: C, 50.41; H, 5.91; N, 23.50; S, 13.46%. Calcd. In addition, it can also replace the nicotinamide to prevent dehydrogenase interference and dehydrogenation, interfere with M. tuberculosis on oxygen utilisation, affect the normal metabolism, and result in the death of bacteria M. tuberculosis. We use cookies to improve your website experience. cstc2015shmszx80060], Chongqing Key Research Project of Basic Science & Frontier Technology [No.