| Identification | More | [Name]
2-Hydroxy-N-(4-hydroxyphenyl)-benzamide | [CAS]
526-18-1 | [Synonyms]
2-hydroxy-n-(4-hydroxyphenyl)-benzamide
LOIRD
N-(4-HYDROXYPHENYL)SALICYLAMIDE
N-SALICYLOYL-P-AMINOPHENOL
OSALMID
2-hydroxy-n-(4-hydroxyphenyl)-benzamid
4’-hydroxy-salicylanilid
4’-hydroxysalicylanilide
4-Hydroxysalicylanilide
auxobil
bilene
bilocol
dribazil
driol
driol-labaz
enidran
hydroxyphenylsalicylamide
l1718
n-(p-hydroxyphenyl)salicylamide
osalmide | [EINECS(EC#)]
208-385-9 | [Molecular Formula]
C13H11NO3 | [MDL Number]
MFCD00020026 | [Molecular Weight]
229.23 | [MOL File]
526-18-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
179° | [Boiling point ]
371.13°C (rough estimate) | [density ]
1.2084 (rough estimate) | [vapor pressure ]
0Pa at 25℃ | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO : ≥ 28 mg/mL (122.15 mM) | [form ]
Solid | [pka]
8.40±0.30(Predicted) | [color ]
White to off-white | [Water Solubility ]
916mg/L at 25℃ | [LogP]
2.47 at 25℃ | [CAS DataBase Reference]
526-18-1(CAS DataBase Reference) | [EPA Substance Registry System]
526-18-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [Toxicity]
LD50 oral in rat: 6702mg/kg |
| Hazard Information | Back Directory | [Uses]
Osalmid is a ribonucleotide reductase small subunit M2 (RRM2) targeting compound; suppresses ribonucleotide reductase activity with an IC50 of 8.23 μM. | [Definition]
ChEBI: Osalmid is an organic molecular entity. | [Biochem/physiol Actions]
Osalmid is a potent inhibitor of ribonucleotide reductase small subunit M2 (RRM2) that potently inhibits HBV DNA and cccDNA synthesis in HepG2.2.15 cells. Osalmid inhibits RR (ribonucleotide reductase) activity in vivo, and exhibits synergistic effect with lamivudine on inactivation mutant HBV strain. Osalmid is a biliation activator (choleretic agent), but a mechanism of this activity remains unknown. | [Synthesis]
To the reaction vessel, 0.07 mol 4-aminophenol, 0.076 mol salicylamide and 80 mL ethyl acetate were added and the stirring speed was controlled to be 150 rpm. 0.031 mol stannous chloride was added slowly and a gradual darkening of the color of the solution was observed. After the addition was completed, the temperature was slowly raised to 170 °C and the reaction was maintained for 6 h. The reaction was carried out at 2.1 °C. After completion of the reaction, vacuum distillation was carried out at 2.1 kPa to remove some of the ethyl acetate. The solution was cooled to 38 °C and subsequently the reaction mixture was poured into 500 mL of sodium bisulfite solution with a mass fraction of 23%. The pH was adjusted to 4 with 33% oxalic acid solution to induce precipitation of the solid. The solid product was separated by filtration and purified by recrystallization with 87% ethylenediamine solution to give 13.47 g of white solid 2-hydroxy-N-(4-hydroxyphenyl)benzamide in 84% yield. | [in vivo]
Osalmid reduces RR activity and HBV replication in HBV-transgenic mice and shows a synergistic efficacy with 3TC without significant toxicity. Oral dosing of osalmid at 400 mg/kg/d results in a time-dependent inhibition of HBV DNA replication. After treatment for 4 weeks, osalmid suppresses HBV DNA replication by about 40-45% as compared to the control in mouse sera and liver tissues[1]. | [storage]
Store at -20°C | [References]
[1] Liu X, et al. Inhibition of hepatitis B virus replication by targeting ribonucleotide reductase M2 protein. Biochem Pharmacol. 2016 Mar 1;103:118-28. DOI:10.1016/j.bcp.2016.01.003 |
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