MALONOBEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H22N2O
Molecular Weight	282.3801
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C

InChI

InChIKey=MZOPWQKISXCCTP-UHFFFAOYSA-N

InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1850195 | https://www.ncbi.nlm.nih.gov/pubmed/22923218 | https://www.ncbi.nlm.nih.gov/pubmed/21527248

Malonoben is a synthetic inhibitor of protein tyrosine kinase (PTK) that displays characteristics of a potent reversible inhibitor of platelet-derived growth factor (PDGF)-induced mitogenesis via inhibition of tyrosine kinase activity of the PDGFR (PDGF receptor) and other signaling cascades. Malonoben significantly attenuated CCR7-induced Pyk2 tyrosine phosphorylation, activation of cofilin and sequentially abolished F-actin rearrangement, diminished the chemotaxis and migration ability of squamous cell carcinoma of the head and neck. Malonoben treatment resulted in the formation of fragmented mitochondria filament. Treatment of malonoben also evoked mitochondrial fragmentation in other cells including the neuroblastomas. Malonoben induces Drp1-mediated mitochondrial fission and apoptotic cell death.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Platelet-derived growth factor receptor 6 Target ID: CHEMBL2095189 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1850195	Inhibitor 8504	0.04 µM [IC50]
Protein tyrosine kinase 2 beta 3 Target ID: CHEMBL5469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22923218 \| https://www.ncbi.nlm.nih.gov/pubmed/18954908	Inhibitor 8504
mitochondrial fission 1 Target ID: GO:0000266 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21527248	Activator 1447
Epidermal growth factor receptor 49 Target ID: CHEMBL2363049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2552117	Inhibitor 8504	155.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Head and neck squamous cell carcinoma 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22923218	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Chemokine receptor 7 via proline-rich tyrosine kinase-2 upregulates the chemotaxis and migration ability of squamous cell carcinoma of the head and neck.	2012-11	22923218
A receptor tyrosine kinase inhibitor, Tyrphostin A9 induces cancer cell death through Drp1 dependent mitochondria fragmentation.	2011-05-13	21527248
Involvement of Ech hydrogenase in energy conservation of Methanosarcina mazei.	2010-08	20629748
Electrochemical elucidation on the mechanism of uncoupling caused by hydrophobic weak acids.	2008-08-14	18654685
D-Aspartate is stored in secretory granules and released through a Ca(2+)-dependent pathway in a subset of rat pheochromocytoma PC12 cells.	2001-07-13	11333256
Ca2+-dependent exocytosis of L-glutamate by alphaTC6, clonal mouse pancreatic alpha-cells.	2001-05	11334403
Inhibitory effect of tyrphostin on the replication of herpes simplex virus type 1.	1995	7544112
Tyrphostins inhibit PDGF-induced DNA synthesis and associated early events in smooth muscle cells.	1991-04	1850195

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The effects of tyrphostin on plaque formation of HSV-1 was examined. In the presence of tyrphostin 9 at the concentration of 200 nM, the plaque number was reduced by 80% in comparison with the control.

Name

Type

Language

MALONOBEN

Common Name

English

GCP-5126

Preferred Name

English

RG-50872

Code

English

2-(3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENE)MALONONITRILE

Systematic Name

English

((3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXYPHENYL)METHYLENE)PROPANEDINITRILE

Systematic Name

English

SF-6847

Code

English

NSC-242557

Code

English

2,6-DI-TERT-BUTYL-4-(2,2-DICYANOVINYL)PHENOL

Systematic Name

English

PROPANEDINITRILE, 2-((3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXYPHENYL)METHYLENE)-

Systematic Name

English

3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENEMALONONITRILE

Systematic Name

English

3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENEMALONITRILE

Systematic Name

English

MALONOBEN [ISO]

Common Name

English

TYRPHOSTIN 9

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

230200