1727-09-9

Basic information

• Product Name: (4-BroMo-benzylaMino)-acetic acid
• Synonyms: (4-BroMo-benzylaMino)-acetic acid;N-(4-Bromobenzyl)glycine
• CAS NO: 1727-09-9
• Molecular Formula: C₉H₁₀BrNO₂
• Molecular Weight: 244.0852
• Mol File: 1727-09-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-BroMo-benzylaMino)-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4-BroMo-benzylaMino)-acetic acid(1727-09-9)
• EPA Substance Registry System: (4-BroMo-benzylaMino)-acetic acid(1727-09-9)

Safety Data

• Hazardous Substances Data: 1727-09-9(Hazardous Substances Data)

Usage

Description

(4-Bromo-benzylamino)-acetic acid is a chemical compound that features a benzene ring with a bromine atom and an amino group attached to it, along with an acetic acid moiety. It is a derivative of acetic acid and is widely used in organic and medicinal chemistry as a starting material for the synthesis of various bioactive compounds. The bromine substituent on the benzyl group endows this compound with unique reactivity, making it suitable for a range of chemical transformations. Additionally, its capacity to interact with biological targets has rendered it a valuable asset in drug discovery and development.

Uses

Used in Organic Chemistry:
(4-Bromo-benzylamino)-acetic acid is used as a starting material for the synthesis of various bioactive compounds due to its unique reactivity and structural features.
Used in Medicinal Chemistry:
(4-Bromo-benzylamino)-acetic acid is used as a building block in the development of pharmaceuticals, leveraging its ability to form interactions with biological targets for drug discovery and design.
Used in Chemical Transformations:
(4-Bromo-benzylamino)-acetic acid is utilized in a variety of chemical reactions due to the reactivity provided by the bromine substituent on the benzyl group, allowing for the creation of diverse chemical entities.

Upstream product

• 6000-43-7 2-aminoethanoic acid hydrochloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 56-40-6 glycine 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 3959-07-7 4-Bromobenzylamine 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 1228660-48-7 1-(4-bromobenzyl)-3-isopropylimidazolidine-2, 4-dione 
• 1228594-55-5 1-(4-bromobenzyl)-3-cyclobutylimidazolidine-2,4-dione 
• 1228660-49-8 1-(4-bromobenzyl)-3-(2,2,2-trifluoroethyl)-imidazolidine-2,4-dione 
• 1228659-84-4 3-isopropyl1-(4-(6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)imidazolidine-2,4-dione 
• 1228660-02-3 3-cyclobutyl-1-(4-(6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)imidazolidine-2,4-dione 
• 1228660-10-3 1-(4-(6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-(2,2,2-trifluoroethyl)imidazolidine-2,4-dione 
• 1228660-00-1 3-cyclopropyl-1-(4-(6-(1,1-dioxo-1λ6-thiomorpholin-4-ylmethyl)-5-fluoropyridin-2-yl)benzyl)imidazolidine-2,4-dione 
• 1228660-41-0 1-(4-bromobenzyl)-3-methylimidazolidine-2,4-dione 
• 1295301-38-0 3-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)imidazolidine-2,4-dione 
• 1228659-50-4 1-(4-(5-fluoro-6-(piperidin-1-ylmethyl)pyridin-2-yl)benzyl)-3-methylimidazolidine-2,4-dione 
• 1295302-08-7 3-cyclopropyl-1-(4-(2-cyclopropyl-1-oxoisoindolin-5-yl)benzyl)imidazolidine-2,4-dione 
• 1228594-48-6 1-(4-bromobenzyl)-3-cyclopropylimidazolidine-2,4-dione 
• 1155051-29-8 2-(4-bromobenzylamino)-N-isopropylacetamide 
• 1156379-10-0 2-(4-bromo-benzylamino)-N-cyclopropyl-acetamide 

Relevant articles and documents

N-benzyl residues as the P10 substituents in phosphorus-containing extended transition state analog inhibitors of metalloaminopeptidases

Peptidyl enzyme inhibitors containing an internal aminomethylphosphinic bond system (P(O)(OH)-CH2-NH) can be termed extended transition state analogs by similarity to the corresponding phosphonamidates (P(O)(OH)-NH). Phosphonamidate pseudopeptides are broadly recognized as competitive mechanism-based inhibitors of metalloenzymes, mainly hydrolases. Their practical use is, however, limited by hydrolytic instability, which is particularly restricting for dipeptide analogs. Extension of phosphonamidates by addition of the methylene group produces a P-C-N system fully resistant in water conditions. In the current work, we present a versatile synthetic approach to such modified dipeptides, based on the three-component phospha-Mannich condensation of phosphinic acids, formaldehyde, and N-benzylglycines. The last-mentioned component allowed for simple and versatile introduction of functionalized P10 residues located on the tertiary amino group. The products demonstrated moderate inhibitory activity towards porcine and plant metalloaminopeptidases, while selected derivatives appeared very potent with human alanyl aminopeptidase (Ki = 102 nM for 6a). Analysis of ligand-protein complexes obtained by molecular modelling revealed canonical modes of interactions for mono-metallic alanyl aminopeptidases, and distorted modes for di-metallic leucine aminopeptidases (with C-terminal carboxylate, not phosphinate, involved in metal coordination). In general, the method can be dedicated to examine P10-S10 complementarity in searching for non-evident structures of specific residues as the key fragments of perspective ligands.

Discovery and optimization of 1-(4-(Pyridin-2-yl)benzyl)imidazolidine-2,4- dione derivatives as a novel class of selective cannabinoid CB2 receptor agonists

Here, we report the identification and optimization of 1-(4-(pyridin-2-yl) benzyl)imidazolidine-2,4-dione derivatives as a novel chemotype with selective cannabinoid CB2 receptor agonist activity. 1 is a potent and selective cannabinoid CB2 receptor agonist (hCB2 pEC50 = 8.6). The compound was found to be metabolically unstable, which resulted in low oral bioavailability in rat (Fpo = 4%) and possessed off-target activity at the hERG ion channel (pKi = 5.5). Systematic modification of physicochemical properties, such as lipophilicity and basicity, was used to optimize the pharmacokinetic profile and hERG affinity of this novel class of cannabinoid CB2 receptor agonists. This led to the identification of 44 as a potent, selective, and orally bioavailable cannabinoid CB2 receptor agonist (hCB2 pEC50 = 8.0; hERG pKi po = 100%), which was active in a rat spinal nerve ligation model of neuropathic pain.

1-(BIPHENYL-4-YLMETHYL)IMIDAZOLIDINE-2,4-DIONE

The invention relates to A 1-(biphenyl-4-ylmethyl)imidazolidine-2,4-dione derivative having the general Formula I wherein R1 is H, (C1-6)alkyl (optionally substituted with oxo, OR4, COOR5, halogen or CN), (C2-6)alkenyl, (C2-6)alkynyl, (C3-6)cycloalkyl or (C3-6)cycloalkyl(C1-3)alkyl; R2 and R2′ are independently H or (C1-3)alkyl; or R2 and R2′ form together with the carbon atom to which they are bound a (C3-5)cycloalkyl group; R3 represents H or 1 to 4 F substituents; Y represents or NR8R9; X represents CHR6, CF2, O, S, SO or SO2; R4 and R5 are (C1-6)alkyl; R6 is H, OR7 or CN; R7 is (C1-3)alkyl; R8 is (C5-7)cycloalkyl comprising a heteroatom selected from O, S, SO and SO2; R9 is H or (C1-4)alkyl; o and m represent the ortho or meta position of the substituent Y—CH2; or a pharmaceutically acceptable salt thereof; as well as to the use of said 1-(biphenyl-4-ylmethyl)imidazolidine-2,4-dione derivatives in the treatment of pain such as for example peri-operative pain, chronic pain, neuropathic pain, cancer pain and pain and spasticity associated with multiple sclerosis.