3544-24-9

The poly(ADP-ribose) polymerases (PARPs) comprise a family of enzymes which post-translationally modify proteins by poly(ADP-ribosyl)ation. Since some PARPs are activated by DNA strand breaks, PARP signaling has roles in DNA repair, apoptosis, inflammation, and other cellular responses. 3-amino Benzamide is an inhibitor of PARPs (K_i = 1.8 μM). Through its effects on PARPs, 3-amino benzamide causes telomere shortening and stimulates angiogenesis. It has PARP-mediated actions in such diverse diseases as atherosclerosis, neurogenesis, and cancer.

beige powder

3-Aminobenzamide is used as an endogenous poly-ADP-ribosyltransferase inhibitor. Through its effects on PARPs, 3-amino benzamide causes telomere shortening and stimulates angiogenesis. It displays neuroprotective, anti-necrotic effects.

The poly(ADP-ribose) polymerases (PARPs) comprise a family of enzymes which post-translationally modify proteins by poly(ADP-ribosyl)ation. Since some PARPs are activated by DNA strand breaks, PARP signaling has roles in DNA repair, apoptosis, inflammation, and other cellular responses. 3-amino Benzamide is an inhibitor of PARPs (Ki = 1.8 μM). Through its effects on PARPs, 3-amino benzamide causes telomere shortening and stimulates angiogenesis. It has PARP-mediated actions in such diverse diseases as atherosclerosis, neurogenesis, and cancer.

ChEBI: A substituted aniline that is benzamide in which one of the meta- hydrogens is replaced by an amino group.

3-Aminobenzamide enhances cell death, unscheduled DNA synthesis and repair replication by interrupting the rejoining of DNA strand breaks induced by both ionizing radiations and several alkylating agents. It has an ability to inhibit the activity of nuclear enzyme poly (ADP-ribose) synthetase (PARS). 3-Aminobenzamide exhibits protective action against myocardial reperfusion injury and local inflammation.

The general procedure for the synthesis of 3-aminobenzamide from 3-nitrobenzamide was as follows: 3-nitrobenzamide (33.3 g, 198.8 mmol) and FeCl3-6H2O (13.6 g, 50.4 mmol) were dissolved in ethanol (600 mL) and activated carbon (15 g) was added. The reaction mixture was heated to 60-65 °C in an oil bath. Hydrazine (30 mL, 85%, 510 mmol) was slowly added through a dropping funnel over 40 minutes. After addition, the reaction continued to be stirred at 60-65 °C for 5 hours. After completion of the reaction, the mixture was filtered under reduced pressure and the filtrate was concentrated. Dichloromethane (400 mL) was added to the concentrate, a precipitate was precipitated, the precipitate was removed by filtration and the filtrate was concentrated to give a white solid. The solid was further purified by recrystallization from ethyl acetate (EA) to give 3-aminobenzamide (21.0 g, 76% yield) as a final white solid. The product was characterized by 1H NMR (DMSO-d6, 400 MHz) and mass spectrometry (ESI+): 1H NMR δ 8.10 (s, 1H), 7.85-7.77 (m, 1H), 7.76 (d, J = 1.8Hz, 1H), 7.59-7.37 (m, 3H), 3.63 (s, 3H); MS (ESI+) m/z 137.1 [M + H]+.

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1) Purnell and Whish (1980), Novel inhibitors of poly(ADP-ribose) synthetase; Biochem. J., 185 775 2) Kuo et al. (1996), Inhibitors of poly(ADP-ribose) polymerase block nitric oxide-induced apoptosis but not differentiation in human leukemia HL-60 cells; Biochem. Biophys. Res. Commun., 219 502 3) Malorni et al. (1995), 3-Aminobenzamide protects cells from UV-B-induced apoptosis by acting on cytoskeleton and substrate adhesion; Biochem. Biophys. Res. Commun., 207 715 4) Heller et al. (1995), Inactivation of the poly(ADP-ribose) polymerase gene affects oxygen radical and nitric oxide toxicity in islet cells; J. Biol. Chem., 270 11176