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=CC=C2C=CC=CC2=C1CC3=C(NC(=S)NC3=O)C4=CC=CC=C4

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 19 Target ID: CHEMBL4506 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16618762	Inhibitor 8504		56.0 µM [IC50]
NAD-dependent deacetylase sirtuin 2 5 Target ID: CHEMBL4462 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16618762	Inhibitor 8504		59.0 µM [IC50]

PubMed

Title	Date	PubMed
Oxidative nucleophilic substitution selectively produces cambinol derivatives with antiproliferative activity on bladder cancer cell lines.	2019-01-01	30442421
Ways to stop the spread of Alzheimer's disease.	2018-07	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.	2018-06-01	29545174
Suppression of tau propagation using an inhibitor that targets the DK-switch of nSMase2.	2018-05-23	29604274
Small Molecules as SIRT Modulators.	2018	27334466
A novel SIRT1 inhibitor, 4bb induces apoptosis in HCT116 human colon carcinoma cells partially by activating p53.	2017-07-01	28526414
Complex role of nicotinamide adenine dinucleotide in the regulation of programmed cell death pathways.	2016-02-01	26343585
The histone deacetylase inhibitor cambinol prevents acidic pHe-induced anterograde lysosome trafficking independently of sirtuin activity.	2015-09	29124170
The histone deacetylase sirtuin 2 is a new player in the regulation of platelet function.	2015-07	25960087
Cambinol, a novel inhibitor of neutral sphingomyelinase 2 shows neuroprotective properties.	2015	26010541
Inhibition of SIRT1 signaling sensitizes the antitumor activity of silybin against human lung adenocarcinoma cells in vitro and in vivo.	2014-07	24798868
Development of pyrazolone and isoxazol-5-one cambinol analogues as sirtuin inhibitors.	2014-04-24	24697269
Frizzled 7 expression is positively regulated by SIRT1 and β-catenin in breast cancer cells.	2014	24897117
High SIRT1 expression is a negative prognosticator in pancreatic ductal adenocarcinoma.	2013-10-02	24088390
The sirtuin inhibitor cambinol impairs MAPK signaling, inhibits inflammatory and innate immune responses and protects from septic shock.	2013-06	23499872
Antitumor effect of SIRT1 inhibition in human HCC tumor models in vitro and in vivo.	2013-04	23339189
SIRT1 positively regulates breast cancer associated human aromatase (CYP19A1) expression.	2013-03	23340254
Cancer chemoprevention and nutriepigenetics: state of the art and future challenges.	2013	22955508
Sirtuin activators and inhibitors.	2012-02-29	22730114
Current advances in the synthesis and antitumoral activity of SIRT1-2 inhibitors by modulation of p53 and pro-apoptotic proteins.	2012	22998567
Antitumor activity of a small-molecule inhibitor of human silent information regulator 2 enzymes.	2006-04-15	16618762

Substance Class	Chemical Created by `admin` on `Wed Apr 02 05:58:57 GMT 2025` Edited by `admin` on `Wed Apr 02 05:58:57 GMT 2025`
Record UNII	8S2PHY4FNC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NSC-112546

Preferred Name

English

CAMBINOL

Common Name

English

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

Systematic Name

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