Benzyl-N-methyl-L-alanine
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Benzyl-N-methyl-L-alanine

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Category
L-Amino Acids
Catalog number
BAT-000393
CAS number
63238-82-4
Molecular Formula
C11H15NO2
Molecular Weight
193.25
IUPAC Name
(2S)-2-[benzyl(methyl)amino]propanoic acid
Synonyms
Bzl-N-Me-L-Ala-OH; (2S)-2-[benzyl(methyl)amino]propanoic acid; N-Methyl-N-Benzylalanine; N-methyl-N-benzyl-l-alanine
Purity
≥ 98% (HPLC)
Melting Point
183-186 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H15NO2/c1-9(11(13)14)12(2)8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3,(H,13,14)/t9-/m0/s1
InChI Key
YEJHUOTUSORYPX-VIFPVBQESA-N
Canonical SMILES
CC(C(=O)O)N(C)CC1=CC=CC=C1
1. Associations between urinary phthalate metabolite concentrations and markers of liver injury in the US adult population
Linling Yu, Meng Yang, Man Cheng, Lieyang Fan, Xing Wang, Tao Xu, Bin Wang, Weihong Chen Environ Int. 2021 Oct;155:106608. doi: 10.1016/j.envint.2021.106608. Epub 2021 May 6.
Background: Phthalates have been largely used for years in varieties of products worldwide. However, research on the joint toxic effect of various phthalates exposure on the liver is lacking. Objectives: We aimed to assess exposure to phthalates on liver function tests (LFTs). Methods: This analysis included data on 6046 adults (≥20 years old) who participated in a National Health and Nutrition Examination Survey (NHANES) in 2007-2016. We employed linear regression and Bayesian kernel machine regression (BKMR), to explore the associations of urinary phthalate metabolites with 8 indicators of LFTs. Results: Di(2-ethylhexyl) phthalate (ΣDEHP) was found to be positively associated with serum alanine aminotransferase (ALT), gamma-glutamyl transferase (GGT) and alkaline phosphatase (ALP) (all P FDR < 0.05). We found significant positive associations of ∑DEHP, mono-ethyl phthalate (MEP) and mono-(carboxyisononyl) phthalate (MCNP) with total bilirubin (TBIL) (all P FDR < 0.05). ΣDEHP, mono-n-butyl phthalate (MBP), mono-(3-carboxypropyl) phthalate (MCPP) and mono-benzyl phthalate (MBzP) were negatively associated with serum ALB (all P FDR < 0.05). The BKMR analyses showed a significantly positive overall effect on ALT, AST, ALP and TBIL levels with high concentrations of phthalate metabolites and a significantly negative overall effect on ALB and TP, when all the chemicals at low concentrations. Conclusions: Our results add novel evidence that exposures to phthalates might be adversely associated with the indicators of LTFs, indicating the potential toxic effect of phthalate exposures on the human liver.
2. N-Cinnamoyl-l-phenyl-alanine methyl ester
Laurent F Bornaghi, Sally-Ann Poulsen, Peter C Healy, Alan R White Acta Crystallogr Sect E Struct Rep Online. 2007 Dec 6;64(Pt 1):o139. doi: 10.1107/S1600536807055973.
As part of an ongoing investigation into the development of N-substituted amino acids as building blocks for dynamic combinatorial chemistry, we report the structure of the title compound, C(19)H(19)NO(3). This compound crystallizes as discrete mol-ecules. The cinnamoyl group is non-planar, with the phenyl ring and the amide twisted out of the ethyl-ene plane. The benzyl and ester groups lie above and below the amide plane. The mol-ecules stack along the crystallographic c axis, connecting through C(4) chains of N-H⋯O hydrogen bonds, with the extended structure stabilized by C-H⋯O inter-actions and π-π inter-actions [centroid-to-centroid distances 3.547 (8) and 3.536 (8) Å].
3. Pharmacological characterization of Ro 63-1908 (1-[2-(4-hydroxy-phenoxy)-ethyl]-4-(4-methyl-benzyl)-piperidin-4-ol), a novel subtype-selective N-methyl-D-aspartate antagonist
R Gill, et al. J Pharmacol Exp Ther. 2002 Sep;302(3):940-8. doi: 10.1124/jpet.102.034322.
Ro 63-1908, 1-[2-(4-hydroxy-phenoxy)-ethyl]-4-(4-methyl-benzyl)-piperidin-4-ol, is a novel subtype-selective N-methyl-D-aspartate (NMDA) antagonist that has been characterized in vitro and in vivo. Ro 63-1908 inhibited [(3)H]dizocilpine ((3)H-MK-801) binding in a biphasic manner with IC(50) values of 0.002 and 97 microM for the high- and low-affinity sites, respectively. Ro 63-1908 selectively blocked recombinant receptors expressed in Xenopus oocytes containing NR1C + NR2B subunits with an IC(50) of 0.003 microM and those containing NR1C + NR2A subunits with an IC(50) of >100 microM, thus demonstrating greater than 20,000-fold selectivity for the recombinant receptors expressing NR1C + NR2B. Ro 63-1908 blocked these NMDA NR2B-subtype receptors in an activity-dependent manner. Ro 63-1908 was neuroprotective against glutamate-induced toxicity and against oxygen/glucose deprivation-induced toxicity in vitro with IC(50) values of 0.68 and 0.06 microM, respectively. Thus, the in vitro pharmacological characterization demonstrated that Ro 63-1908 was a potent and highly selective antagonist of the NR2B subtype of NMDA receptors. Ro 63-1908 was active against sound-induced seizures (ED(50) = 4.5 mg/kg i.p. when administered 30 min beforehand) in DBA/2 mice. The dose required to give a full anticonvulsant effect did not produce a deficit in the Rotarod test. NMDA-induced seizures were also inhibited by Ro 63-1908 with an ED(50) of 2.31 mg/kg i.v. when administered 15 min before testing. Ro 63-1908 gave a dose-related neuroprotective effect against cortical damage in a model of permanent focal ischemia. Maximum protection of 39% was seen at a plasma concentration of 450 ng/ml. There were, however, no adverse cardiovascular or CNS side-effects seen at this dosing level.
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