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2-Amino-3,3,3-trifluoro-propionic acid hydrochloride - CAS 96105-72-5

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Category
Main Product
Product Name
2-Amino-3,3,3-trifluoro-propionic acid hydrochloride
Catalog Number
96105-72-5
Synonyms
2-Amino-3,3,3-trifluoro-propionic acid hydrochloride;3,3,3-Trifluoroalanine hydrochloride
CAS Number
96105-72-5
Molecular Weight
179.53
Molecular Formula
C3H5ClF3NO2
COA
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MSDS
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Structure
CAS 96105-72-5 2-Amino-3,3,3-trifluoro-propionic acid hydrochloride
Specification
Purity
95%
Boiling Point
254.9ºC at 760mmHg
Density
g/cm3
Reference Reading
1.Preparation of optically active (2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic acid (threo-beta-phenylserine) via optical resolutions by replacing and preferential crystallization.
Shiraiwa T1, Kawashima Y, Ikaritani A, Suganuma Y, Saijoh R. Chem Pharm Bull (Tokyo). 2006 Aug;54(8):1170-4.
To obtain optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (1) via optical resolutions by replacing and preferential crystallization, the racemic structure of (2RS,3SR)-1 hydrochloride [(2RS,3SR)-1.HCl] was examined based on the melting point, solubility, and infrared spectrum. (2RS,3SR)-1.HCl was indicated to exist as a conglomerate at room temperature, although it forms a racemic compound at the melting point. When, in optical resolution by replacing crystallization, L-phenylalanine methyl ester hydrochloride (L-2) was used as the optically active co-solute, (2R,3S)-1.HCl was preferentially crystallized from the supersaturated racemic solution; the use of D-2 as the co-solute afforded (2S,3R)-1.HCl with an optical purity of 95%. In addition, optical resolution by preferential crystallization was successfully achieved to give successively (2R,3S)- and (2S,3R)-1.HCl with optical purities of 90-92%. The (2R,3S)- and (2S,3R)-1.
2.Effect of glutamate receptor antagonists on place aversion induced by naloxone in single-dose morphine-treated rats.
Kawasaki Y1, Jin C, Suemaru K, Kawasaki H, Shibata K, Choshi T, Hibino S, Gomita Y, Araki H. Br J Pharmacol. 2005 Jul;145(6):751-7.
The neurobiological mechanism underlying the negative motivational component of withdrawal from acute opiate dependence is far from understood. Our objectives were to determine whether the glutamatergic system is involved in the motivational component of morphine withdrawal in acutely dependent rats and such an involvement is associated with dopaminergic neurotransmission. We examined the effects of various kinds of glutamate receptor antagonists on conditioned place aversion (CPA) induced by naloxone-precipitated withdrawal from a single morphine exposure 24 h before. Furthermore, the influence of pretreatment with the dopamine receptor antagonist haloperidol on those effects of glutamate receptor antagonists was also investigated. CPA was attenuated in a dose-dependent manner by all glutamate receptor antagonists examined including the NMDA receptor antagonists (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclo-hepten-5,10-imine maleate (MK-801) and phencyclidine hydrochloride (PCP), AMPA receptor antagonist 1-(4-aminophenyl)4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride (GYKI 52466), and metabotropic receptor antagonists (+/-)-2-amino-3-phosphonopropionic acid (AP-3) and (+/-)-alpha-methyl-4-carboxyphenylglycine (MCPG).
3.Synthesis of new 3-pyridinecarboxylates of potential vasodilation properties.
Girgis AS1, Mishriky N, Farag AM, El-Eraky WI, Farag H. Eur J Med Chem. 2008 Sep;43(9):1818-27. doi: 10.1016/j.ejmech.2007.11.025. Epub 2007 Dec 8.
2-(alicyclic-amino)-4,6-diaryl-3-pyridinecarboxylates 5a-d were prepared via aromatic nucleophilic substitution reaction of secondary amines (piperidine or morpholine) with 2-bromo-3-pyridinecarboxylate derivatives 3a,b. The latters were obtained through bromination of 3-aryl-4-benzoyl-2-cyanobutyrates 2a and 2b, which were obtained from the base promoted addition of ethyl cyanoacetate to 2-propen-1-ones 1a and 1b, with bromine in glacial acetic acid. Reaction of 3 with piperazine hexahydrate in 2:1 molar ratio afforded 1,4-bis[(ethyl 4,6-diaryl-3-pyridinecarboxylate)-2-yl]piperazines 6a,b. Reaction of 3 with anilines in refluxing pyridine unexpectedly gave 2-(aryl-amino)-3-pyridinecarboxylates 8a-g and 2-amino-3-pyridinecarboxylates 9a and 9b. Vasodilation activity screening for the synthesized pyridinecarboxylates using isolated thoracic aortic rings' standard method of rats shows considerable properties. Compounds 5b, 5c, 6b and 8g reveal remarkable vasodilation potency (IC50, concentrations necessary for 50% reduction of maximal norepinephrine hydrochloride induced contracture) 0.
4.A thioredoxin reductase and/or thioredoxin system-based mechanism for antioxidant effects of ambroxol.
Huang J1, Xu J2, Tian L3, Zhong L4. Biochimie. 2014 Feb;97:92-103. doi: 10.1016/j.biochi.2013.09.024. Epub 2013 Oct 5.
Long-term treatment with ambroxol (ABX), a bronchial expectorant, was found to prevent acute exacerbation of chronic obstructive pulmonary disease (AECOPD). The underlying mechanism remains unclear. To address this, we have investigated the effect of ABX on critical antioxidant proteins thioredoxin (Trx) and thioredoxin reductase (TrxR) that are decreased in patients with AECOPD. Trx, TrxR and NADP(H) form Trx system, which is involved in regulating numerous oxidative stress-related events. In human bronchial epithelial cells, treatment with ABX from 0 to 200 μM gradually increased mRNA and protein levels of TrxR/Trx. At these ABX concentrations, TrxR activity was elevated progressively, whereas Trx activity exhibited a dose-dependent biphasic response, increasing at 50 and 75 μM, but decreasing at ABX over 150 μM. Pre-treatment with 75 μM ABX enhanced the capacity of the cells to eliminate reactive oxygen species, which was largely prevented by knockdown of cytosolic Trx (hTrx1).
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