14513-15-6

Basic information

• Product Name: NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone
• Synonyms: Cambinol;NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone;5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one;5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone;NSC-1125476;Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone;SIRT1/2 Inhibitor IV, Cambinol;SIRT1/2 Inhibitor IV
• CAS NO: 14513-15-6
• Molecular Formula: C21H16N2O2S
• Molecular Weight: 360.435
• Mol File: 14513-15-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 235 °C(dec.)
• Boiling Point: 667°Cat760mmHg
• Flash Point: 357.2°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 2.12E-18mmHg at 25°C
• Refractive Index: 1.771
• Storage Temp.: Room temp
• Solubility: DMSO: ≥10mg/mL
• CAS DataBase Reference: NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone(CAS DataBase Reference)
• NIST Chemistry Reference: NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone(14513-15-6)
• EPA Substance Registry System: NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone(14513-15-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 14513-15-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 14513-15-6 differently. You can refer to the following data:
1. SIRT1/2 Inhibitor IV, Cambinol is an inhibitor of SIRT1, SIRT2, and SIRT5.
2. Cambinol has been used:as an inhibitor of sirutins (SIRT1 and 2) in hepatocarcinoma cell lines to test its effect on cellular viability and colony formationas a SIRT1 and SIRT2 inhibitor to test its effect on frizzled 7 (FZD7) expression in the breast cancer cells MDA-MB-231 and T-47D cellsas a sirutin inhibitor in L929 cells to test its protective effect against tumor necrosis factor (TNF)-induced cell death

Biochem/physiol Actions

Cambinol is a Sirtuin (Human Silent Information Regulator) Type 1/2 Inhibitor. Sirtuins are structurally and mechanistically unrelated to HDACs Class 1 & 2 deacetylases but share many protein targets. HDAC is a large complex enzyme family involved in epigenetic-control of gene expression. Sirt2 has an IC50 equal to 59 μM.

references

heltweg b, gatbonton t, schuler ad, et al. antitumor activity of a small-molecule inhibitor of human silent information regulator 2 enzymes. cancer res. 2006 apr 15;66(8):4368-77.laemmle a, lechleiter a, roh v, et al. inhibition of sirt1 impairs the accumulation and transcriptional activity of hif-1α protein under hypoxic conditions. plos one. 2012;7(3):e33433.

InChI:InChI=1/C21H16N2O2S/c24-18-11-10-13-6-4-5-9-15(13)16(18)12-17-19(14-7-2-1-3-8-14)22-21(26)23-20(17)25/h1-11,24H,12H2,(H2,22,23,25,26)