Methyl 3-[[[2-methoxy-4-(phenylamino)phenyl]amino]sulfonyl]-2-thiophenecarboxylate

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H18N2O5S2
Molecular Weight	418.487
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of Methyl 3-[[[2-methoxy-4-(phenylamino)phenyl]amino]sulfonyl]-2-thiophenecarboxylate

Structure Search

SMILES

COC(=O)C1=C(C=CS1)S(=O)(=O)NC2=C(OC)C=C(NC3=CC=CC=C3)C=C2

InChI

InChIKey=NDFKBGWLUHKMFY-UHFFFAOYSA-N

InChI=1S/C19H18N2O5S2/c1-25-16-12-14(20-13-6-4-3-5-7-13)8-9-15(16)21-28(23,24)17-10-11-27-18(17)19(22)26-2/h3-12,20-21H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C19H18N2O5S2
Molecular Weight	418.487
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22606335 | https://www.ncbi.nlm.nih.gov/pubmed/23500098

GSK 0660 is a selective PPARdelta antagonist. The compound reduced psoriasis-like changes in a preclinical model and demonstrated neuroprotection in an in vitro model of Parkinson’s disease. When given alone GSK 0660 exhibits inverse agonist effects.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor delta 30 Target ID: Q03181\|\|\|Q9BUD4 Gene ID: 5467.0 Gene Symbol: PPARD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17975020	Inverse Agonist 85		0.155 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23500098	Primary		Basic research	Unknown Approved Use Unknown
Psoriasis 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22606335	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
RNA-seq identifies a role for the PPARβ/δ inverse agonist GSK0660 in the regulation of TNFα-induced cytokine signaling in retinal endothelial cells.	2015	26015769
The natural protective mechanism against hyperglycemia in vascular endothelial cells: roles of the lipid peroxidation product 4-hydroxydodecadienal and peroxisome proliferator-activated receptor delta.	2010-04	20107107
Endothelium-dependent vasodilator effects of peroxisome proliferator-activated receptor beta agonists via the phosphatidyl-inositol-3 kinase-Akt pathway.	2010-02	19906781
Identification and characterization of a selective peroxisome proliferator-activated receptor beta/delta (NR1C2) antagonist.	2008-02	17975020

Patents

Sample Use Guides

In Vivo Use Guide

Mice were shaved on their abdomen and were treated twice daily with ointment containing 0.5% GSK0660 (preclinical study).

Route of Administration: Topical

In Vitro Use Guide

SH-SY5Y cells were treated with 100 nM GSK 0660 and it was found that GSK0660 (100 nM) and GSK0660 pretreatment followed by co-treatment with GW0742 (10 nM) increased the MPP+-induced decrease in cell viability compared to MPP+ alone.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 05:52:34 GMT 2025` Edited by `admin` on `Wed Apr 02 05:52:34 GMT 2025`
Record UNII	NLW7Q75SNS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Methyl 3-[[[2-methoxy-4-(phenylamino)phenyl]amino]sulfonyl]-2-thiophenecarboxylate

Systematic Name

English

2-Thiophenecarboxylic acid, 3-[[[2-methoxy-4-(phenylamino)phenyl]amino]sulfonyl]-, methyl ester

Preferred Name

English

Methyl 3-((2-methoxy-4-phenylazanyl-phenyl)sulfamoyl)thiophene-2-carboxylate

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID10673163

Created by admin on Wed Apr 02 05:52:34 GMT 2025 , Edited by admin on Wed Apr 02 05:52:34 GMT 2025

PRIMARY

CAS

1014691-61-2

Created by admin on Wed Apr 02 05:52:34 GMT 2025 , Edited by admin on Wed Apr 02 05:52:34 GMT 2025

PRIMARY

PUBCHEM

46233311

Created by admin on Wed Apr 02 05:52:34 GMT 2025 , Edited by admin on Wed Apr 02 05:52:34 GMT 2025

PRIMARY

FDA UNII

NLW7Q75SNS

Created by admin on Wed Apr 02 05:52:34 GMT 2025 , Edited by admin on Wed Apr 02 05:52:34 GMT 2025

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22606335 | https://www.ncbi.nlm.nih.gov/pubmed/23500098

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22606335 | https://www.ncbi.nlm.nih.gov/pubmed/23500098