(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone - CAS 152305-23-2

An intermediate of Zolmitriptan, as a novel inhibitor of the cytochrome P-450 enzyme aromatase. Zolmitriptan USP Related Compound G.

Catalog Number

152305-23-2

CAS

152305-23-2

IUPAC Name

(4S)-4-[(4-aminophenyl)methyl]-1,3-oxazolidin-2-one

Synonyms

(4S)-4-[(4-aminophenyl)methyl]-2-oxazolidinone; (4S)-4-[(4-aminophenyl)methyl]-1,3-oxazolidin-2-one

Molecular Weight

192.21

Molecular Formula

C10H12N2O2

Product Information

Canonical SMILES

C1C(NC(=O)O1)CC2=CC=C(C=C2)N

InChI

InChI=1S/C10H12N2O2/c11-8-3-1-7(2-4-8)5-9-6-14-10(13)12-9/h1-4,9H,5-6,11H2,(H,12,13)/t9-/m0/s1

InChI Key

WNAVSKJKDPLWBD-VIFPVBQESA-N

Purity

≥ 98 %

MDL

MFCD03411476

Physical State

Solid

Appearance

Powder or crystals

Storage

Room temperature.

Boiling Point

479.7 °C at 760 mmHg

Melting Point

110 °C

Density

1.257 g/cm³

Optical Activity

-6° (c=1 in methanol)

Solubility

Soluble in dimethyl sulfoxide and methanol.

TSCA

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

Hazard Statements

H302 - H315 - H319 - H335

Reference Reading

1. Design, Synthesis, And evaluation of 4-(4'-aminobenzyl)-2-oxazolidinones as novel inhibitors of the cytochrome p-450 enzyme aromatase.

Yonas Amanuel, Sabbir Ahmed, Caroline P Owen, Shaheen Adat, Annabel Murrells. Bioorg Chem. 2002 Oct; 30(5): 315-31. DOI: 10.1016/s0045-2068(02)00017-2. PMID: 12485592.

The synthesis of a series of N-alkylated 4-(4(')aminobenzyl)-2-oxazolidinones is described using a synthetically useful scheme which avoids the use of phosgene-since the derivatization is undertaken with the oxazolidin-2-one ring intact. The compounds were tested for human placental aromatase (AR) inhibition in vitro, using [1beta,2beta-3H]androstenedione as substrate for the AR enzyme. The compounds were found, in general, to be more potent than the standard compound, aminoglutethimide (AG), and as such proved to be good lead compounds in the search for more specific AR inhibitors.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass