410536-97-9

Basic information

• Product Name: SIRTINOL
• Synonyms: 2-[(2-HYDROXYNAPHTHALEN-1-YLMETHYLENE)AMINO]-N-(1-PHENETHYL)BENZAMIDE;SIRTINOL;SIR TWO INHIBITOR NAPHTHOL;2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide;2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide;(E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide
• CAS NO: 410536-97-9
• Molecular Formula: C₂₆H₂₂N₂O₂
• Molecular Weight: 394.47
• Product Categories: Other enzyme inhibitors and activators;Other Enzyme Inhibitors.;Inhibitor;Inhibitors
• Mol File: 410536-97-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 119-120℃
• Boiling Point: 650°Cat760mmHg
• Flash Point: 211.4°C
• Appearance: /
• Density: 1.16
• Vapor Pressure: 8.88E-17mmHg at 25°C
• Refractive Index: 1.711
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 30 mg/ml).
• PKA: 7.85±0.50(Predicted)
• Water Solubility: Soluble in water, DMSO and methanol
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
• CAS DataBase Reference: SIRTINOL(CAS DataBase Reference)
• NIST Chemistry Reference: SIRTINOL(410536-97-9)
• EPA Substance Registry System: SIRTINOL(410536-97-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 410536-97-9(Hazardous Substances Data)

Usage

Description

SIRTINOL, also known as a 2-hydroxy-1-naphthaldehyde derivative, is a cell-permeable compound that acts as a specific and direct inhibitor of the sirtuin class of deacetylase activity. It is particularly effective against human SIRT1, human SIRT2, and yeast Sir2, with no effect on human HDAC1. SIRTINOL is active both in vivo and in purified enzyme studies, making it a promising candidate for various applications.

Uses

Used in Pharmaceutical Applications:
SIRTINOL is used as an inhibitor of the NAD+-Dependent Protein Desuccinylase and Demalonylase Sirt5, exhibiting anticancer properties. It modulates several cellular processes and pathways, making it a potential therapeutic agent for cancer treatment.
Used in Enzyme Inhibition Studies:
SIRTINOL is used as a cell-permeable specific inhibitor of sirtuin NAD-dependent deacetylases, such as human SIRT1, human SIRT2, and yeast Sir2. It is employed in research to study the effects of sirtuin inhibition on various cellular processes and to understand the role of these enzymes in disease progression.
Used in Drug Development:
SIRTINOL is used as a lead compound in the development of new drugs targeting sirtuin enzymes. Its specificity and cell permeability make it an attractive candidate for the development of novel therapeutics for various diseases, including cancer.
Used in Research and Development:
SIRTINOL is used as a research tool to study the role of sirtuin enzymes in cellular processes and disease mechanisms. It helps researchers understand the molecular basis of sirtuin inhibition and its potential therapeutic applications.

Biological Activity

Cell-permeable, selective sirtuin deacetylase inhibitor (IC 50 values are 38, 68 and 131 μ M at SIRT2, Sir2p and SIRT1 respectively) that has no effect on HDAC1 activity. Significantly decreases growth and viability of PCa and HEK293T cells in vitro .

Biochem/physiol Actions

Cell permeable: yes

References

1) Ota et al. (2006) SIRT1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells; Oncogene, 25 176 2) Mai et al. (2005) Design, synthesis and biological evaluation of sirtinol analogues as class III histone/protein deacetylase (Sirtuin) inhibitors; J. Med. Chem. 48 7789 3) Grozinger et al. (2001) Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening; J. Biol. Chem. 276 38837 4) Koering et al. (2002) Human telomeric position effect is determined by chromosomal context and telomeric chromatin integrity; EMBO Rep. 3 1055

InChI:InChI=1/C26H22N2O2/c1-18(19-9-3-2-4-10-19)28-26(30)22-13-7-8-14-24(22)27-17-23-21-12-6-5-11-20(21)15-16-25(23)29/h2-18,27H,1H3,(H,28,30)/t18-/m0/s1

Upstream product

• 85592-80-9 2-amino-N-(1-phenylethyl)benzamide 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 118-48-9 isatoic anhydride 
• 618-36-0 rac-methylbenzylamine 

Relevant articles and documents

Green and catalyst-free one-pot synthesis of anthranilamide Schiff bases: An approach toward sirtinol

A novel and simple method for the green one-pot synthesis of anthranilamide Schiff bases is described. The reported Schiff bases are obtained via the reaction of isatoic anhydride, amines, and aromatic aldehydes in water at room temperature, without using any catalysts. No cyclization toward 2,3-dihydro-4(1H)-quinazolinones occurred in this method and anthranilamide Schiff bases were produced exclusively. This approach offers a green method to prepare the medicinally important Schiff base sirtinol and other bioactive anthranilamide Schiff bases. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright