4-[1-Chloro-2-(methylamino)ethyl]phenyl acetate hydrochloride

Name: 4-[1-Chloro-2-(methylamino)ethyl]phenyl acetate hydrochloride
SKU: ACM14593250
Rating: 5 (1 reviews)

CAS

14593-25-0

Catalog Number

ACM14593250

Category

Main Products

Molecular Weight

264.15

Molecular Formula

C₁₁H₁₅Cl₂NO₂

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Specification

Synonyms

Glucocorticoid Receptor Modulator, CpdA, 2-((4-Acetoxyphenyl)-2-chloro-N-methyl)ethylammonium chloride, 4-[1-CHLORO-2-(METHYLAMINO)ETHYL]PHENYL ACETATE HYDROCHLORIDE, 14593-25-0, PubChem19319, AKOS015888247, I01-10419

IUPAC Name

[4-[1-chloro-2-(methylamino)ethyl]phenyl] acetate;hydrochloride

InChI Key

WKMYTPCPAWZWII-UHFFFAOYSA-N

Boiling Point

324.6ºC at 760 mmHg

Flash Point

150.1ºC

Exact Mass

263.04800

H-Bond Acceptor

H-Bond Donor

Effects of the Glucocorticoid Receptor Modulator Compound A on a Collagen-Induced Arthritis Model

Rauner, Martina, et al. Endocrinology, 2013, 154(10), 3719-3728.

Compound A (CpdA) is a selective glucocorticoid (GC) receptor modulator. This work used the collagen-induced arthritis model - a mouse form of rheumatoid arthritis - to explore whether CpdA might also protect bone under proinflammatory conditions. The evidence is that CpdA moderately inhibits inflammation while concurrent effects on bone remain unknown, and CpdA might better be used as a molecular tool to analyse GC function.
Evaluation methods and results
· CpdA reduced disease activity, paw swelling, and paw temperature by 43%, 12%, and 7%, respectively, although it was less effective than dexamethasone (DEX), which achieved reductions of 72%, 22%, and 10% in these parameters.
· Additionally, T cells isolated from animals treated with CpdA and DEX exhibited lower activity, as evidenced by reduced proliferation rates following a challenge with type II collagen. These T cells also produced smaller amounts of interferon-γ and TNF compared to T cells from PBS-treated mice.
· Histological assessments of the joints indicated that CpdA was less effective than DEX in preventing the infiltration of inflammatory cells, the stimulation of osteoclastogenesis, and the degradation of articular cartilage.
· Due to the absence of arthritis models that are susceptible to glucocorticoids (GC), it was unable to thoroughly investigate the bone-sparing potential of CpdA in inflammatory conditions. However, the bone formation marker procollagen type 1 N-terminal peptide, which serves as an indicator of GC-mediated inhibition of bone formation, was significantly reduced by DEX in arthritic mice, while CpdA did not show this effect.

Mechanistic Study of Compound A (CpdA) Inhibiting Bladder Cancer Growth

Zheng, Yichun, et al. Molecular Endocrinology, 2015, 29(10), 1486-1497.

This work evaluated the effect of 2-(4-acetoxyphenyl)-2-chloro-N-methylethylammonium chloride (compound A [CpdA]), which acts not only as a GC receptor (GR) modulator but also as an androgen receptor (AR) antagonist, on bladder cancer growth. It is likely that CpdA primarily inhibits bladder cancer growth by inducing GR transrepression, which may be partially mediated through the AR pathway, indicating its potential advantages over glucocorticoids, pure GR ligands, or AR antagonists.
· In cells that are positive for both glucocorticoid receptors (GR) and androgen receptors (AR), Compound A (CpdA) significantly reduced cell proliferation and colony formation while also increasing the population of cells arrested in the G1 phase and enhancing apoptotic activity. Specifically, at a concentration of 1 μM, CpdA resulted in a 50% reduction in cell viability for TCCSUP/UMUC3-control-short hairpin RNA (shRNA), a 67% reduction for TCCSUP/UMUC3-GR-shRNA, and a 38% reduction and 58% for TCCSUP/UMUC3-AR-shRNA.
· Furthermore, CpdA inhibited cell migration and invasion in GR/AR-positive lines by as much as 61%, in GR-positive/AR-silencing lines by up to 51%, and in GR-silencing/AR-positive lines with a lower efficacy of up to 35%.
· In studies with male mice bearing UMUC3-control xenografts, CpdA demonstrated a stronger tumor growth suppression compared to dexamethasone or hydroxyflutamide.
· Additionally, CpdA reduced transcriptional activities of nuclear factor (NF)-κB and activator protein 1, which suggests it leads to GR-mediated transrepression.

What is the molecular formula of the compound?

The molecular formula of the compound is C11H15Cl2NO2.

What are the synonyms of the compound?

The synonyms of the compound are 14593-25-0, 4-[1-Chloro-2-(methylamino)ethyl]phenyl acetate hydrochloride, 4-(1-Chloro-2-(methylamino)ethyl)phenyl acetate hydrochloride, Glucocorticoid Receptor Modulator, CpdA, and [4-[1-chloro-2-(methylamino)ethyl]phenyl]acetate;hydrochloride.

What is the molecular weight of the compound?

The molecular weight of the compound is 264.14 g/mol.

What is the parent compound of the compound?

The parent compound of the compound is 4-(1-Chloro-2-(methylamino)ethyl)phenyl acetate.

What are the component compounds of the compound?

The component compounds of the compound are 4-(1-Chloro-2-(methylamino)ethyl)phenyl acetate and hydrochloric acid.

When was the compound created and modified?

The compound was created on October 25, 2006, and last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name of the compound is [4-[1-chloro-2-(methylamino)ethyl]phenyl]acetate;hydrochloride.

What is the InChI of the compound?

The InChI of the compound is InChI=1S/C11H14ClNO2.ClH/c1-8(14)15-10-5-3-9(4-6-10)11(12)7-13-2;/h3-6,11,13H,7H2,1-2H3;1H.

What is the InChIKey of the compound?

The InChIKey of the compound is WKMYTPCPAWZWII-UHFFFAOYSA-N.

What are the computed properties of the compound?

The computed properties of the compound include the molecular weight (264.14 g/mol), hydrogen bond donor count (2), hydrogen bond acceptor count (3), rotatable bond count (5), exact mass (263.0479841 g/mol), topological polar surface area (38.3Å²), heavy atom count (16), formal charge (0), complexity (203), isotope atom count, defined atom stereocenter count, undefined atom stereocenter count, defined bond stereocenter count, undefined bond stereocenter count, covalently-bonded unit count, and whether the compound is canonicalized (yes).