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142026

Sigma-Aldrich

Benzoyleneurea

97%

Synonym(s):

2,4(1H,3H)-Quinazolinedione

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About This Item

Empirical Formula (Hill Notation):
C8H6N2O2
CAS Number:
86-96-4
Molecular Weight:
162.15
EC Number:
201-712-6
MDL number:
MFCD00006699
UNSPSC Code:
12352100
PubChem Substance ID:
24848378
NACRES:
NA.22

Assay

97%

form

powder

mp

300 °C (lit.)

solubility

ammonium hydroxide: soluble 10 mg/mL
DMF: soluble
alcohols: slightly soluble

SMILES string

O=C1NC(=O)c2ccccc2N1

InChI

1S/C8H6N2O2/c11-7-5-3-1-2-4-6(5)9-8(12)10-7/h1-4H,(H2,9,10,11,12)

InChI key

SDQJTWBNWQABLE-UHFFFAOYSA-N

Application

Benzoyleneurea scaffold was used in the synthesis of novel protein geranylgeranyltransferase-I inhibitors. It was used to study the mechanism of inactivation of chymotrypsin and other serine proteases by benzoxazinones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J Michel et al.
Nucleic acids research, 24(6), 1127-1135 (1996-03-15)
A major limitation in triple-helix formation arises from the weak energy of interaction between the third strand and the double-stranded target. We tried to increase the stacking interaction contribution within the third strand by extending the aromatic domain of thymine.
P Lundquist et al.
Analytical biochemistry, 211(1), 23-27 (1993-05-15)
A fluorometric high-performance liquid-chromatographic method is described for the determination of cyanate in human plasma. The method is based on the derivatization of cyanate with 2-aminobenzoic acid (anthranilic acid), leading to a stable cyclic fluorescent product, 2,4(1H,3H)-quinazolinedione. The fluorescent product
Katie J Aldred et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(7), E839-E846 (2016-01-23)
Mycobacterium tuberculosis is a significant source of global morbidity and mortality. Moxifloxacin and other fluoroquinolones are important therapeutic agents for the treatment of tuberculosis, particularly multidrug-resistant infections. To guide the development of new quinolone-based agents, it is critical to understand
R Stribling et al.
Journal of molecular evolution, 32, 282-288 (1991-01-01)
Previous attempts to produce nonenzymatic template-directed oligomerizations of activated pyrimidines on polypurine templates have been unsuccessful. The only efficient reactions are those where the template is composed primarily of pyrimidines, especially cytosine. Because molecular evolution requires that a synthesized daughter
Hiroki Kakuta et al.
Chemical & pharmaceutical bulletin, 51(11), 1273-1282 (2003-11-06)
Potent, specific, chemically stable and non-peptide/small-molecular inhibitors of puromycin-sensitive aminopeptidase, such as 3-(2,6-diethylphenyl)-2,4(1H,3H)-quinazolinedione (PAQ-22, 5), were prepared by the structural development of a potent PSA inhibitor, 2-(2,6-diethylphenyl)-1,2,3,4-tetrahydroisoquinoline-1,3-dione (PIQ-22, 4). The design was carried out partly by applying electrostatic potential field
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