DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H18Cl3FN4O3S
Molecular Weight	555.836
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA

Structure Search

SMILES

[O-][N+](=O)C1=C(F)C=CC(NC(=S)NC(NC(=O)C(C2=CC=CC=C2)C3=CC=CC=C3)C(Cl)(Cl)Cl)=C1

InChI

InChIKey=HLCDNLNLQNYZTK-UHFFFAOYSA-N

InChI=1S/C23H18Cl3FN4O3S/c24-23(25,26)21(30-22(35)28-16-11-12-17(27)18(13-16)31(33)34)29-20(32)19(14-7-3-1-4-8-14)15-9-5-2-6-10-15/h1-13,19,21H,(H,29,32)(H2,28,30,35)

HIDE SMILES / InChI

Molecular Formula	C23H18Cl3FN4O3S
Molecular Weight	555.836
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16767085 | https://www.ncbi.nlm.nih.gov/pubmed/18560433
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18347191 | https://www.ncbi.nlm.nih.gov/pubmed/19903334 | http://www.selleckchem.com/products/cgk-733.html | https://www.ncbi.nlm.nih.gov/pubmed/24795863 | https://www.ncbi.nlm.nih.gov/pubmed/21865098

Diphenyl acetamidotrichloroethyl fluoronitrophenyl thiourea, CGK733, was claimed to be selective inhibitor of the ataxia telangiectasia-mutated (ATM) protein and ATM- and Rad3-related (ATR) protein, however after investigation of the contents of the original paper by Korean Advanced Institute of Science and Technology (KAIST) several irregularities has been revealed and the paper was retracted in full. Further studies were completed showing that CGK-733 has no specific inhibitory effect on ATM or ATR. Unfortunately, the compound is still being marketed as an ATM/ATR inhibitor. CGK733 inhibits the proliferation of human cancer and non-transformed mouse fibroblast cell lines and induced senescent breast, lung, and colon carcinoma cells to undergo cell death.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19903334	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19903334 https://www.ncbi.nlm.nih.gov/pubmed/26259235 https://www.ncbi.nlm.nih.gov/pubmed/22564734 https://www.ncbi.nlm.nih.gov/pubmed/18347191	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Small molecule-based reversible reprogramming of cellular lifespan.	2006 Jul	16767085
Ataxia telangiectasia mutated and p21CIP1 modulate cell survival of drug-induced senescent tumor cells: implications for chemotherapy.	2008 Mar 15	18347191
The ATM and ATR inhibitors CGK733 and caffeine suppress cyclin D1 levels and inhibit cell proliferation.	2009 Nov 10	19903334
CGK733 does not inhibit ATM or ATR kinase activity in H460 human lung cancer cells.	2011 Oct 10	21865098
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.	2011 Oct 30	22037377
CGK733 enhances multinucleated cell formation and cytotoxicity induced by taxol in Chk1-deficient HBV-positive hepatocellular carcinoma cells.	2012 May 25	22564734
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.	2013 Apr 15	23398362

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

10 uM CGK733 inhibits cell proliferation in MCF-7, T47D and MDA-MB436 breast cancer cells, LNCaP prostate cancer cells, HCT116 colon cancer cells and BALB/c 3T3 fibroblasts

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:22:16 GMT 2023` Edited by `admin` on `Sat Dec 16 10:22:16 GMT 2023`
Record UNII	L3DGZ99QYM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA

Official Name

English

DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA [INCI]

Common Name

English

ATM/ATR KINASE INHIBITOR

Common Name

English

CGK 733

Code

English

CGK733

Brand Name

English

CGK-733

Code

English

BENZENEACETAMIDE, .ALPHA.-PHENYL-N-(2,2,2-TRICHLORO-1-((((4-FLUORO-3-NITROPHENYL)AMINO)THIOXOMETHYL)AMINO)ETHYL)-

Systematic Name

English

Code System Code Type Description

CAS

905973-89-9

Created by admin on Sat Dec 16 10:22:16 GMT 2023 , Edited by admin on Sat Dec 16 10:22:16 GMT 2023

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FDA UNII

L3DGZ99QYM

Created by admin on Sat Dec 16 10:22:16 GMT 2023 , Edited by admin on Sat Dec 16 10:22:16 GMT 2023

PRIMARY

EPA CompTox

DTXSID30424997

Created by admin on Sat Dec 16 10:22:16 GMT 2023 , Edited by admin on Sat Dec 16 10:22:16 GMT 2023

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PUBCHEM

6605258

Created by admin on Sat Dec 16 10:22:16 GMT 2023 , Edited by admin on Sat Dec 16 10:22:16 GMT 2023

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SERINE-PROTEIN KINASE ATM

TARGET -> INHIBITOR

Details

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Approved Use

PubMed

Patents

Sample Use Guides