(3-Amino-benzyl)-carbamic acid tert-butyl ester
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(3-Amino-benzyl)-carbamic acid tert-butyl ester

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(3-Amino-benzyl)-carbamic acid tert-butyl ester (CAS# 147291-66-5) is a useful research chemical.

Category
Other Unnatural Amino Acids
Catalog number
BAT-008919
CAS number
147291-66-5
Molecular Formula
C12H18N2O2
Molecular Weight
222.28
(3-Amino-benzyl)-carbamic acid tert-butyl ester
IUPAC Name
tert-butyl N-[(3-aminophenyl)methyl]carbamate
Synonyms
Tert-Butyl 3-aminobenzylcarbamate
Appearance
Solid
Purity
> 95 %
Density
1.1±0.1 g/cm3
Boiling Point
386.0±25.0 ℃ at 760 mmHg
InChI
InChI=1S/C12H18N2O2/c1-12(2,3)16-11(15)14-8-9-5-4-6-10(13)7-9/h4-7H,8,13H2,1-3H3,(H,14,15)
InChI Key
LSOZALWRNWQPLK-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCC1=CC(=CC=C1)N
1. N-(2-oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: synthesis and structure-activity and structure-property relationships
Andrea Duranti, et al. J Med Chem. 2012 May 24;55(10):4824-36. doi: 10.1021/jm300349j. Epub 2012 May 10.
The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure-activity and structure-property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC(50) = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.
2. Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines
J Jang, K S Sin, H Park Arch Pharm Res. 2001 Dec;24(6):503-7. doi: 10.1007/BF02975153.
trans-Metanicotine, a subtype (alpha4beta2)-selective ligand for neuronal nicotinic acetylcholine receptor, is under clinical phase for Alzheimer's disease. An efficient synthetic route for (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines, derivatives of trans-metanicotine, was explored. Allylation reaction of aryl aldimines with allylmagnesium bromide in THF gave (+/-)-methyl-(1-aryl-but-3-enyl)-amines. Protection of the amines with the Boc group and following Heck reaction of the N-Boc amines with 3-bromopyridine gave (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-carbamic acid tert-butyl esters. Deprotection of the N-Boc group in aqueous 1N-HCI solution gave the titled amines in good yields. Thus, trans-metanicotine analogues modified at the a-position of the methylamino group with aryl groups were obtained in 5 steps.
3. Newborn screening for Pompe disease by measuring acid alpha-glucosidase activity using tandem mass spectrometry
Angéla Dajnoki, Adolf Mühl, György Fekete, Joan Keutzer, Joe Orsini, Victor Dejesus, X Kate Zhang, Olaf A Bodamer Clin Chem. 2008 Oct;54(10):1624-9. doi: 10.1373/clinchem.2008.107722. Epub 2008 Aug 14.
Background: Pompe disease, caused by the deficiency of acid alpha-glucosidase (GAA), is a lysosomal storage disorder that manifests itself in its most severe form within the first months of life. Early detection by newborn screening is warranted, since prompt initiation of enzyme replacement therapy may improve morbidity and mortality. We evaluated a tandem mass spectrometry (MS/MS) method to measure GAA activity for newborn screening for Pompe disease. Methods: We incubated 3.2-mm punches from dried blood spots (DBS) for 22 h with the substrate [7-benzoylamino-heptyl)-{2-[4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenylcarbamoyl]- ethyl}-carbamic acid tert-butyl ester] and internal standard [7-d(5)-benzoylamino-heptyl)-[2-(4-hydroxy-phenylcarbamoyl)-ethyl]-carbamic acid tertbutyl ester]. We quantified the resulting product and internal standard using MS/MS. We assessed inter- and intrarun imprecision, carryover, stability, and correlation between enzyme activities and hematocrit and punch location and generated a Pompe disease-specific cutoff value using routine newborn screening samples. Results: GAA activities in DBS from 29 known Pompe patients were <2 micromol/h/L. GAA activities in routine newborn screening samples were [mean (SD)] 14.7 (7.2) micromol/h/L (n = 10,279, median 13.3, 95% CI 14.46-14.74 micromol/h/L) and in normal adult samples 9.3 (3.3) micromol/h/L (n = 229, median 9, 95% CI 8.88-9.72 micromol/h/L). GAA activity was stable for 28 days between 37 degrees C and -80 degrees C. Carryover could not be observed, whereas intrarun and interrun imprecision were <10%. The limit of detection was 0.26 micromol/h/L and limit of quantification 0.35 micromol/h/L. Conclusions: The measurement of GAA activities in dry blood spots using MS/MS is suitable for high-throughput analysis and newborn screening for Pompe disease.
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