10040-86-5

Basic information

• Product Name: 4-CHLOROBENZALHYDANTOIN
• Synonyms: 4-CHLOROBENZALHYDANTOIN
• CAS NO: 10040-86-5
• Molecular Formula: C₁₀H₇ClN₂O₂
• Molecular Weight: 222.63
• Mol File: 10040-86-5.mol

Chemical Properties

• Appearance: /
• Density: 1.45g/cm³
• Refractive Index: 1.654
• CAS DataBase Reference: 4-CHLOROBENZALHYDANTOIN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZALHYDANTOIN(10040-86-5)
• EPA Substance Registry System: 4-CHLOROBENZALHYDANTOIN(10040-86-5)

Safety Data

• Hazardous Substances Data: 10040-86-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-CHLOROBENZALHYDANTOIN is used as a halogenating agent for the modification of aromatic compounds, facilitating the introduction of halogen atoms into organic molecules.
Used in Pharmaceutical Preparation:
4-CHLOROBENZALHYDANTOIN is used as a reagent in the preparation of various pharmaceuticals, contributing to the synthesis of medicinal compounds.
Used in Production of Organic Chemicals:
4-CHLOROBENZALHYDANTOIN is a key intermediate in the production of other organic chemicals, playing a crucial role in the synthesis of a range of chemical products.
Safety Precautions:
4-CHLOROBENZALHYDANTOIN should be handled with caution, as it is a potential irritant to the skin, eyes, and respiratory system. Exposure to high concentrations can have harmful effects on health.

InChI:InChI=1/C10H7ClN2O2/c11-7-3-1-6(2-4-7)5-8-9(14)13-10(15)12-8/h1-5H,(H2,12,13,14,15)/b8-5-

Upstream product

• 120697-22-5 5-(p-chlorobenzylidene)hydantoin 
• 461-72-3 2,4-imidazolidinedione 
• 104-88-1 4-chlorobenzaldehyde 
• 95378-36-2 diethyl 2,4-dioxoimidazolidin-5-yl-phosphonate 
• 37428-88-9 5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one 
• 139488-42-9 3-Acetyl-5-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one 

Downstream Products

• 1388167-21-2 C₁₃H₁₁ClN₂O₃ 
• 1388167-32-5 (Z)-5-(4-chlorobenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1-yl)-2-hydroxypropyl)imidazolidine-2,4-dione 
• 1388167-36-9 (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 1388167-49-4 (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl)imidazolidine-2,4-dione 
• 937050-04-9 C₁₆H₂₀ClN₃O₃ 
• 6331-81-3 5-(4-chlorobenzyl)imidazolidine-2,4-dione 
• 6331-81-3 5-(4-chlorobenzyl)imidazolidine-2,4-dione 
• 867041-26-7 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(3-trifluoromethyl-phenyl)-acetamide 
• 867041-32-5 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide 
• 867041-17-6 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(4-chloro-phenyl)-acetamide 
• 127273-12-5 3-(4-chlorophenyl)-2-hydroxyacrylic acid 
• 6331-81-3 5-(4-Chlorobenzyl)imidazolidine-2,4-dione 
• 120697-22-5 5-(p-chlorobenzylidene)hydantoin 

Relevant articles and documents

A new approach for the conversion of thiohydantoin to hydantoin derivatives

The reaction of thiohydantoins with 1-(bromoacetyl)benzenes afforded the corresponding hydantoin derivatives and 1-(mercaptoacetyl)benzenes instead of the expected oxoimidazothiazoles.

Synthesis and Biological Evaluation of Novel Dispiro Compounds based on 5-Arylidenehydantoins and Isatins as Inhibitors of p53–MDM2 Protein–Protein Interaction

[Figure not available: see fulltext.] A series of novel hydantoin-based dispiroindolinones as potential small-molecule inhibitors of p53–MDM2 protein–protein interaction were synthesized by two methods, using 2-arylidenehydantoins as starting materials. S

Synthesis of dispirooxindoles containing N-unsubstituted heterocyclic moieties and study of their anticancer activity

A convenient method is proposed for the synthesis of N-unsubstituted spiroxindoles with different heterocyclic moieties (2-thiohydantoin, hydantoin, and thiazolidine) by the regio-selective 1,3-dipolar cycloaddition of azomethine ylides, generated from is

The marine natural-derived inhibitors of glycogen synthase kinase-3β phenylmethylene hydantoins: In vitro and in vivo activities and pharmacophore modeling

The Red Sea sponge Hemimycale arabica afforded the known (Z)-5-(4-hydroxybenzylidene)-hydantoin (1). This natural phenylmethylene hydantoin (PMH) 1 and the synthetic (Z)-5-(4-(ethylthio)benzylidene)-hydantoin (2) showed potent in vitro and in vivo anti-gr

Evaluation of α-hydroxycinnamic acids as pyruvate carboxylase inhibitors

Through a structure-based drug design project (SBDD), potent small molecule inhibitors of pyruvate carboxylase (PC) have been discovered. A series of α-keto acids (7) and α-hydroxycinnamic acids (8) were prepared and evaluated for inhibition of PC in two assays. The two most potent inhibitors were 3,3′-(1,4-phenylene)bis[2-hydroxy-2-propenoic acid] (8u) and 2-hydroxy-3-(quinoline-2-yl)propenoic acid (8v) with IC50 values of 3.0 ± 1.0 μM and 4.3 ± 1.5 μM respectively. Compound 8v is a competitive inhibitor with respect to pyruvate (Ki = 0.74 μM) and a mixed-type inhibitor with respect to ATP, indicating that it targets the unique carboxyltransferase (CT) domain of PC. Furthermore, compound 8v does not significantly inhibit human carbonic anhydrase II, matrix metalloproteinase-2, malate dehydrogenase or lactate dehydrogenase.

Synthesis of chiral hydantoin derivatives by homogeneous Pd-catalyzed asymmetric hydrogenation

5-Aryl substituted chiral hydantoin derivatives were synthesized via asymmetric hydrogenation of prochiral exocyclic alkenes using a Pd/BINAP catalyst. Moderate to good enantioselectivity were obtained (21–90% ee). A chiral Br?nsted acid additive was foun

Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP)

C-terminal Binding Protein (CtBP) is a transcriptional co-regulator that downregulates the expression of many tumor-suppressor genes. Utilizing a crystal structure of CtBP with its substrate 4-methylthio-2-oxobutyric acid (MTOB) and NAD+ as a guide, we have designed, synthesized, and tested a series of small molecule inhibitors of CtBP. From our first round of compounds, we identified 2-(hydroxyimino)-3-phenylpropanoic acid as a potent CtBP inhibitor (IC50 = 0.24 μM). A structure-activity relationship study of this compound further identified the 4-chloro- (IC50 = 0.18 μM) and 3-chloro- (IC50 = 0.17 μM) analogues as additional potent CtBP inhibitors. Evaluation of the hydroxyimine analogues in a short-term cell growth/viability assay showed that the 4-chloro- and 3-chloro-analogues are 2-fold and 4-fold more potent, respectively, than the MTOB control. A functional cellular assay using a CtBP-specific transcriptional readout revealed that the 4-chloro- and 3-chloro-hydroxyimine analogues were able to block CtBP transcriptional repression activity. This data suggests that substrate-competitive inhibition of CtBP dehydrogenase activity is a potential mechanism to reactivate tumor-suppressor gene expression as a therapeutic strategy for cancer.

NOVEL N3-AMINOALKYL DERIVATIVES OF 5-ARYLIDENEHYDANTOIN, PHARMACEUTICAL COMPOSITION CONTAINING THE ABOVE AND APPLICATION THEREOF

The invention discloses novel 3-aminoalkyl derivatives of 5-arylidenehydantoin of formula I, pharmaceutical composition containing these derivatives and the use thereof in inhibition of efflux of drugs used to prevent and treat diseases of bacterial and/o

Search for new tools to combat Gram-negative resistant bacteria among amine derivatives of 5-arylidenehydantoin

A series of amine-alkyl derivatives of 5-arylidenehydantoin 3-21 was evaluated for their ability to improve antibiotic effectiveness in two strains of Gram-negative Enterobacter aerogenes: the reference strain (ATCC-13048) and the chloramphenicol-resistan

Synthesis and SAR-study for novel arylpiperazine derivatives of 5-arylidenehydantoin with α1-adrenoceptor antagonistic properties

The study is focused on a series of 5-arylidenehydantoin derivatives with a phenylpiperazine-hydroxypropyl fragment at N3 of the hydantoin ring. The compounds were assessed on their affinity for α1-adrenoceptors and evaluated in functional bioassays for their antagonistic properties. Crystal structures of (Z)-5-(4-chlorobenzylidene)-3-(3-(4-(2-ethoxyphenyl)piperazin-1- yl)-2-hydroxypropyl)imidazolidine-2,4-dione (7) and hydrochloride of (Z)-5-(4-chlorobenzylidene)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl) propyl)imidazolidine-2,4-dione (10a) were solved using the X-ray diffraction method. Classical molecular mechanics (MMFFs force field, MCMM, MacroModel) were used to predict 3D structure of compounds 5a-18a using a crystal structure of 7. SAR analysis was performed on the basis of Barbaro's pharmacophore model and structural properties of previously investigated α1- adrenoceptor antagonists possessing a hydantoin fragment. Most of the compounds exhibited significant affinities for α1-ARs in nanomolar range (40-290 nM). The highest activities (Ki 1-affinities as follows: 3,4-di CH3O>2,4-di CH3O>4-Cl>2,3-di CH 3O>H>4-N(CH3)2.