Boc-L-1,2,3,4-tetrahydronorharman-3-carboxylic acid
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Boc-L-1,2,3,4-tetrahydronorharman-3-carboxylic acid

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Boc-L-1,2,3,4-tetrahydronorharman-3-carboxylic acid (CAS# 66863-43-2) is a useful research chemical.

Category
BOC-Amino Acids
Catalog number
BAT-001348
CAS number
66863-43-2
Molecular Formula
C17H20N2O4
Molecular Weight
316.36
Boc-L-1,2,3,4-tetrahydronorharman-3-carboxylic acid
IUPAC Name
(3S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid
Synonyms
Boc-L-Tpi-OH
Appearance
White solid
Purity
≥ 98 % (HPLC)
Density
1.3±0.1 g/cm3
Melting Point
286-291 ℃
Boiling Point
532.7±50.0 ℃
Storage
Store at 2-8 ℃
InChI
InChI=1S/C17H20N2O4/c1-17(2,3)23-16(22)19-9-13-11(8-14(19)15(20)21)10-6-4-5-7-12(10)18-13/h4-7,14,18H,8-9H2,1-3H3,(H,20,21)/t14-/m0/s1
InChI Key
FHEPEWKHTOVVAT-AWEZNQCLSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CC2=C(CC1C(=O)O)C3=CC=CC=C3N2
1. Cross-Coupling Reactions of 5-Bromo-1,2,3-triazine
Lukas V Hoff, Joana M Hauser, Karl Gademann J Org Chem. 2022 Nov 18;87(22):15684-15692. doi: 10.1021/acs.joc.2c02082. Epub 2022 Oct 28.
An efficient Pd catalyzed cross-coupling method for 5-bromo-1,2,3-triazine is described. Optimization of the reaction conditions allowed for the preparation of a representative scope of (hetero)aryl-1,2,3-triazines (20 examples, up to 97% yield). The reaction scope was evaluated using a data science enabled boronic acid chemical space to assess the generality of the method. Additionally, diversification of the resulting products enabled the preparation of pyrimidines and pyridines in yields of up to 80% and in only two steps.
2. New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)
José Luis Viveros-Ceballos, Lizeth A Matías-Valdez, Francisco J Sayago, Carlos Cativiela, Mario Ordóñez Amino Acids. 2021 Mar;53(3):451-459. doi: 10.1007/s00726-021-02962-4. Epub 2021 Mar 1.
Two new strategies for the efficient synthesis of racemic 1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid (TicP) (±)-2 have been developed. The first strategy involves the electron-transfer reduction of the easily obtained α,β-dehydro phosphonophenylalanine followed by a Pictet-Spengler cyclization. The second strategy involves a radical decarboxylation-phosphorylation reaction on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic). In both strategies, the highly electrophilic N-acyliminium ion is formed as a key intermediate, and the target compound is obtained in good yield using mild reaction conditions and readily available starting materials, complementing existing methodologies and contributing to the easy accessibility of (±)-2 for further research.
3. 3-Pyridinylboronic acid normalizes the effects of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine exposure in zebrafish embryos
Fümet Duygu Üstündağ, İsmail Ünal, Derya Cansız, Ünsal Veli Üstündağ, Hülya Kara Subaşat, A Ata Alturfan, Pınar Mega Tiber, Ebru Emekli-Alturfan Drug Chem Toxicol. 2022 Mar;45(2):947-954. doi: 10.1080/01480545.2020.1795189. Epub 2020 Jul 21.
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a neurotoxin that damages dopaminergic neurons. Zebrafish has been shown to be a suitable model organism to investigate the molecular pathways in the pathogenesis of Parkinson's disease and also for potential therapeutic agent research. Boron has been shown to play an important role in the neural activity of the brain. Boronic acids are used in combinatorial approaches in drug design and discovery. The effect of 3-pyridinylboronic acid which is an important sub-class of heterocyclic boronic acids has not been evaluated in case of MPTP exposure in zebrafish embryos. Accordingly, this study was designed to investigate the effects of 3-pyridinylboronic acid on MPTP exposed zebrafish embryos focusing on the molecular pathways related to neurodegeneration and apoptosis by RT-PCR. Zebrafish embryos were exposed to MPTP (800 μM); MPTP + Low Dose 3-Pyridinylboronic acid (50 μM) (MPTP + LB) and MPTP + High Dose 3-Pyridinylboronic acid (100 μM) (MPTP + HB) in well plates for 72 hours post fertilization. Results of our study showed that MPTP induced a P53 dependent and Bax mediated apoptosis in zebrafish embryos and 3-pyridinylboronic acid restored the locomotor activity and gene expressions related to mitochondrial dysfunction and oxidative stress due to the deleterious effects of MPTP, in a dose-dependent manner.
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