CAMBINOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H16N2O2S
Molecular Weight	360.429
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(CC2=C(NC(=S)NC2=O)C3=CC=CC=C3)C4=CC=CC=C4C=C1

InChI

InChIKey=RVNSQVIUFZVNAU-UHFFFAOYSA-N

InChI=1S/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)

HIDE SMILES / InChI

Molecular Formula	C21H16N2O2S
Molecular Weight	360.429
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NAD-dependent deacetylase sirtuin 1 16 Target ID: CHEMBL4506 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16618762	Inhibitor 8297		56.0 µM [IC50]
NAD-dependent deacetylase sirtuin 2 5 Target ID: CHEMBL4462 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16618762	Inhibitor 8297		59.0 µM [IC50]

PubMed

Title	Date	PubMed
Antitumor activity of a small-molecule inhibitor of human silent information regulator 2 enzymes.	2006 Apr 15	16618762
Sirtuin activators and inhibitors.	2012 Sep-Oct	22730114
Cancer chemoprevention and nutriepigenetics: state of the art and future challenges.	2013	22955508
Antitumor effect of SIRT1 inhibition in human HCC tumor models in vitro and in vivo.	2013 Apr	23339189
High SIRT1 expression is a negative prognosticator in pancreatic ductal adenocarcinoma.	2013 Oct 2	24088390
Development of pyrazolone and isoxazol-5-one cambinol analogues as sirtuin inhibitors.	2014 Apr 24	24697269
Cambinol, a novel inhibitor of neutral sphingomyelinase 2 shows neuroprotective properties.	2015	26010541
The histone deacetylase sirtuin 2 is a new player in the regulation of platelet function.	2015 Jul	25960087
The histone deacetylase inhibitor cambinol prevents acidic pH(e)-induced anterograde lysosome trafficking independently of sirtuin activity.	2015 Sep	29124170
A novel SIRT1 inhibitor, 4bb induces apoptosis in HCT116 human colon carcinoma cells partially by activating p53.	2017 Jul 1	28526414
Small Molecules as SIRT Modulators.	2018	27334466
Ways to stop the spread of Alzheimer's disease.	2018 Jul	30046082
Inhibition of sirtuins 1 and 2 impairs cell survival and migration and modulates the expression of P-glycoprotein and MRP3 in hepatocellular carcinoma cell lines.	2018 Jun 1	29545174
Suppression of tau propagation using an inhibitor that targets the DK-switch of nSMase2.	2018 May 23	29604274
Oxidative nucleophilic substitution selectively produces cambinol derivatives with antiproliferative activity on bladder cancer cell lines.	2019 Jan 1	30442421

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:35:11 GMT 2023` Edited by `admin` on `Sat Dec 16 15:35:11 GMT 2023`
Record UNII	8S2PHY4FNC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAMBINOL

Common Name

English

4(1H)-PYRIMIDINONE, 2,3-DIHYDRO-5-((2-HYDROXY-1-NAPHTHALENYL)METHYL)-6-PHENYL-2-THIOXO-

Systematic Name

English

NSC-112546

Code

English

2,3-DIHYDRO-5-((2-HYDROXY-1-NAPHTHALENYL)METHYL)-6-PHENYL-2-THIOXO-4(1H)-PYRIMIDINONE

Systematic Name

English

Code System Code Type Description

CAS

14513-15-6