327026-97-1

Basic information

• Product Name: 2-BROMO-N-(5-CHLORO-2HYDROXYPHENYL)-2-METHYLPROPIONAMIDE
• Synonyms: 2-BROMO-N-(5-CHLORO-2HYDROXYPHENYL)-2-METHYLPROPIONAMIDE
• CAS NO: 327026-97-1
• Molecular Formula: C₁₀H₁₁BrClNO₂
• Molecular Weight: 292.55684
• Mol File: 327026-97-1.mol

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 410.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.633±0.06 g/cm3(Predicted)
• PKA: 8.77±0.48(Predicted)
• CAS DataBase Reference: 2-BROMO-N-(5-CHLORO-2HYDROXYPHENYL)-2-METHYLPROPIONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-N-(5-CHLORO-2HYDROXYPHENYL)-2-METHYLPROPIONAMIDE(327026-97-1)
• EPA Substance Registry System: 2-BROMO-N-(5-CHLORO-2HYDROXYPHENYL)-2-METHYLPROPIONAMIDE(327026-97-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 327026-97-1(Hazardous Substances Data)

Upstream product

• 95-85-2 2-hydroxy-5-chloro-aniline 
• 20769-85-1 2-bromoisobutyric acid bromide 

Downstream Products

• 327026-98-2 2-bromo-N-(5-chloro-2-hydroxy-3-nitro-phenyl)-2-methyl-propionamide 
• 124188-37-0 6-chloro-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one 

Relevant articles and documents

Benzo six-membered nitrogen heterocyclic compound, preparation method and applications

The present invention provides a benzo six-membered nitrogen heterocyclic compound, a preparation method and applications, wherein the benzo six-membered nitrogen heterocyclic compound has a structurerepresented by a formula I or formula II, and can effectively inhibit the bromine domain receptor and effectively inhibit the proliferation of cancer cells. Compared with the existing reported structure types, the compound of the present invention has different binding mode, has high inhibitory activity, can be used as a drug for treating cancer, cell proliferation disorders, inflammatory diseases, autoimmune diseases, septicemia and viral infections, and has good application prospects and high application value.

PHENYLPIPERAZINES AS SEROTONIN REUPTAKE INHIBITORS

The invention relates to a novel group of phenylpiperazines having interesting pharmacological properties such as a high affinity for the dopamine D2 receptor and/or the serotonin reuptake site, and the ability to treat conditions related to disturbances

Synthesis, structure-activity relationships, and biological properties of 1-heteroaryl-4-[ω-(1H-indol-3-yl)alkyl]piperazines, novel potential antipsychotics combining potent dopamine D2 receptor antagonism with potent serotonin reuptake inhibition

A series of novel bicyclic 1-heteroaryl-4-[ω-(1H-indol-3-yl)alkyl] piperazines was synthesized and evaluated on binding to dopamine D2 receptors and serotonin reuptake sites. This class of compounds proved to be potent in vitro dopamine D2 receptor antagonists and in addition were highly active as serotonin reuptake inhibitors. Some key representatives showed potent pharmacological in vivo activities after oral dosing in both the antagonism of apomorphine-induced climbing and the potentiation of 5-HTP-induced behavior in mice. On the basis of the preclinical data, 8-{4-[3-(5-fluoro-1H- indol-3-yl)propyl]piperazin-1-yl}-4H-benzo[1,4]oxazin-(R)-2-methyl-3-one (45c, SLV314) was selected for clinical development. In vitro and in vivo studies revealed that 45c has favorable pharmacokinetic properties and a high CNS plasma ratio. Molecular modeling studies showed that the bifunctional activity of 45c can be explained by its ability to adopt two different conformations fitting either the dopamine D2 receptor pharmacophore or the serotonin transporter pharmacophore.

Synthesis by microwave irradiation of a substituted benzoxazine parallel library with preferential relaxant activity for guinea pig trachealis

An efficient, facile, and practical parallel combinatorial synthesis of substituted-benzoxazines under microwave irradiation was described. The procedure involved the use of a microwave oven especially designed for organic synthesis suitable for parallel synthesis of solution libraries. A demonstration 19-membered library of substituted N,N-dimethyl- and N-methyl-benzoxazine amide derivatives, structurally related to the potassium channel opener cromakalim, was generated by both conventional and microwave procedures, achieving a reduction from 7 h to 30-36 min in library generation time for the microwave approach. All the synthesized compounds were tested using the in vitro models of rat aorta and guinea pig trachea rings pre-contracted with phenylephrine and carbachol, respectively. All N,N-dimethyl amide derivatives showed a relaxant activity higher on guinea pig trachea rings than on rat aorta rings.

Synthesis and vasorelaxant activity of new 1,4-benzoxazine derivatives potassium channel openers

As part of a search for new potassium channel openers, the synthesis and vasorelaxant activity of new 1,4-benzoxazine derivatives derived from transformation of the benzopyran skeleton of cromakalim were described. Several new 1,4-benzoxazine derivatives were provided with significant vasorelaxant activity with an overall pharmacological behavior similar to CRK (1f, 1i, 2d, 2e, 2f and 2i).

Synthesis, biological activity and conformational study of 1,4- benzoxazine derivatives as potassium channel modulators

With the aim of discovering new molecules with K+-channel activating properties, we have synthesized derivatives of cromakalim (CRK), an important molecule which shows specific affinity towards K+ channels, by replacing the benzopyrane ring of this reference compound with a 1,4-benzoxazine moiety. A different number of substituents showing a good discrimination between hydrophobic and electronic properties have been inserted at the 6-position of the 1,4-benzoxazine ring. We describe here the synthesis and discuss the solid state conformation of these new molecules. When tested on rat aorta ring precontracted with phenylephrine, two compounds (2c and 2d) showed a concentration-dependent relaxation similar to that measured for cromakalim but less potent than this reference drug.