3-Aminobenzamide Chemical Properties

Melting point:

115-116 °C (lit.)

Boiling point:

250.42°C (rough estimate)

Density 

1.1778 (rough estimate)

refractive index 

1.5769 (estimate)

storage temp. 

room temp

solubility 

ethanol: 50 mg/mL, clear, faintly yellow

form 

powder

pka

16.26±0.50(Predicted)

color 

white to off-white

Water Solubility 

Soluble in dimethylformamide (~30 mg/ml), dimethyl sulfoxide (~30 mg/ml), phosphate buffered saline (pH7.2) (~2 mg/ml), water (25 mg/ml), and ethanol (25 mg/ml).

Sensitive 

Light Sensitive

BRN 

2802373

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

LogP

-0.330

CAS DataBase Reference

3544-24-9(CAS DataBase Reference)

NIST Chemistry Reference

3-NH2-C6H4CONH2(3544-24-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

RIDADR 

3077

WGK Germany 

3

RTECS 

CU8992000

HS Code 

29242990

Hazardous Substances Data

3544-24-9(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Aminobenzamide Usage And Synthesis

Description

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.

Chemical Properties

beige powder

Uses

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.

Uses

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.

Definition

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

Biochem/physiol Actions

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.

Synthesis

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]+.

References

[1] M R PURNELL  W J W. Novel inhibitors of poly(ADP-ribose) synthetase.[J]. Biochemical Journal, 1980, 185 3: 775-777. DOI:10.1042/bj1850775
[2] MIN-LIANG KUO . Inhibitors of Poly(ADP-ribose) polymerase Block Nitric Oxide-Induced Apoptosis but Not Differentiation in Human Leukemia HL-60 Cells[J]. Biochemical and biophysical research communications, 1996, 219 2: Pages 502-508. DOI:10.1006/bbrc.1996.0263
[3] MALORNI W. 3-Aminobenzamide Protects Cells from UV-B-Induced Apoptosis by Acting on Cytoskeleton and Substrate Adhesion[J]. Biochemical and biophysical research communications, 1995, 207 2: Pages 715-724. DOI:10.1006/bbrc.1995.1246
[4] B HELLER. Inactivation of the poly(ADP-ribose) polymerase gene affects oxygen radical and nitric oxide toxicity in islet cells.[J]. The Journal of Biological Chemistry, 1995, 270 19: 11176-11180. DOI:10.1074/jbc.270.19.11176

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