1,3-DIPHENYLUREA

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H12N2O
Molecular Weight	212.2472
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(NC1=CC=CC=C1)NC2=CC=CC=C2

InChI

InChIKey=GWEHVDNNLFDJLR-UHFFFAOYSA-N

InChI=1S/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)

HIDE SMILES / InChI

Description
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01628a079 | https://www.ncbi.nlm.nih.gov/pubmed/18585390

1,3-Diphenylurea is a cytokinin first identified in coconut milk. It is a hormone that promotes cell division in plant roots and shoots. 1,3-Diphenylurea is a nanomolar inhibitor of epoxide hydrolase B from Mycobacterium tuberculosis and its derivatives were developed for the treatment of tuberculosis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Epoxide hydrolase 1 Target ID: CHEMBL1795155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21840723	Inhibitor 8504		19.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18585390	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification of wastewater bacteria involved in the degradation of triclocarban and its non-chlorinated congener.	2010-11-15	20727675
Dual-target-directed 1,3-diphenylurea derivatives: BACE 1 inhibitor and metal chelator against Alzheimer's disease.	2010-08-01	20620068
Cytokinin-induced structural adaptability of a Lupinus luteus PR-10 protein.	2009-03	19220853
In vitro biologic activities of the antimicrobials triclocarban, its analogs, and triclosan in bioassay screens: receptor-based bioassay screens.	2008-09	18795164
Fate of triclosan and evidence for reductive dechlorination of triclocarban in estuarine sediments.	2008-06-15	18605588
3,3'-Diphenyl-1,1'-[2,2'-oxybis(2,1-phenyl-ene)]diurea N,N-dimethyl-formamide disolvate.	2007-12-18	21200869
The RET kinase inhibitor NVP-AST487 blocks growth and calcitonin gene expression through distinct mechanisms in medullary thyroid cancer cells.	2007-07-15	17638907
Electrochemically controlled hydrogen bonding. Redox-dependent formation of a 2:1 diarylurea/dinitrobenzene2- complex.	2005-12-23	16356005
Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas.	2005-05-04	15853350
Inhibition of neuronal Na+ channels by the novel antiepileptic compound DCUKA: identification of the diphenylureido moiety as an inactivation modifier.	2002-11	12460615
Metabolism of diphenylurea by a Marinobacter sp. isolated from a contaminated ephemeral stream bed in the Negev Desert.	2002-08-06	12167538

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

IC50 values were determined using fluorescent substrate cyano(6-methoxy-naphthalen-2-yl) methyl trans-[(3-phenyloxiran-2-yl)methyl] carbonate (compound 6). Mycobacterium tuberculosis epoxide hydrolase B ([E] ~30 nM; 1.5 g/ml) was incubated with inhibitor ([I]=5–100,000 nM) for 5 min in BisTris–HCl buffer (25 mM, pH 7.0, containing 0.1 mg/ml of bovine serum albumin) at 30 °C prior to substrate introduction ([S]=5 μM). Enzyme activity was measured by monitoring the appearance of fluorescent of 6-methoxy-naphthaldehyde (λex 330 nm and λem 465 nm).

Name

Type

Language

1,3-DIPHENYLUREA

Systematic Name

English

CARBANILIDE

Preferred Name

English

DIPHENYLUREA, 1,3-

Systematic Name

English

CARBANILIDE [HSDB]

Common Name

English

CARBANILIDE [MI]

Common Name

English

NSC-227401

Code

English

Code System Code Type Description

NSC

227401