81167-39-7Relevant articles and documents
Synthesis of fluorescent dipeptidomimetics and their ribosomal incorporation into green fluorescent protein
Roy Chowdhury, Sandipan,Maini, Rumit,Dedkova, Larisa M.,Hecht, Sidney M.
, p. 4715 - 4718 (2015)
The synthesis and incorporation into position 66 of green fluorescent protein (GFP) by in vitro protein translation of novel oxazole and thiazole based dipeptidomimetics are described. The compounds may be regarded as GFP chromophore analogues, and are strongly fluorescent. An α-amido-β-ketoester intermediate was obtained via bisacylation of a protected glycine. The intermediate underwent dehydrative cyclization to afford the 1,3-oxazole and was treated with Lawesson's reagent to furnish the 1,3-thiazole. When these fluorophores were introduced into position 66 of GFP in place of Tyr66, the resulting GFP analogues exhibited fluorescence emission several-fold greater than wild-type GFP; the emission was also shifted to shorter wavelength. It may be noted that compared to the typical fluorophores formed in the natural and modified fluorescent proteins, the oxazole and thiazole fluorophores are completely stable and do not require activation by posttranslational modification to exhibit fluorescence.
Synthesis of β-Hydroxy α-Amino Acids through Br?nsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
Vera, Silvia,Vázquez, Ana,Rodriguez, Ricardo,Pozo, Sandra Del,Urruzuno, I?aki,de Cózar, Abel,Mielgo, Antonia,Palomo, Claudio
, p. 7757 - 7772 (2021/06/21)
Here we report the highly enantio- and syn-selective synthesis of β-hydroxy α-amino acids from glycine imine derivatives under Br?nsted base (BB) catalysis. The key of this approach is the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.
PROCESSES FOR THE PREPARATION OF 4-{8-AMINO-3-[(2S)-1-(BUT-2-YNOYL)-PYRROLIDIN-2-YL]IMIDAZO[1,5-A]-PYRAZIN-1-YL}N-(PYRIDIN-2-YL)-BENZAMIDE
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Paragraph 00230, (2020/03/23)
The present disclosure relates, in general, to improved processes for the preparation of 4-{8-amino-3-[(2S)-1-(but-2-ynoyl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)-benzamide, particularly large-scale processes for manufacturing 4-{8-amino-3-[(2S)-1-(but-2-ynoyl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide and intermediates used in such processes.
NOVEL OPIOID ANTAGONISTS AND METHODS RELATED THERETO
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Paragraph 0046, (2020/05/14)
Disclosed is a composition and method for a therapeutic treatment that is able to combat certain conditions such as alcohol dependence, opioid abuse treatment, neurological disorders, neuropathic pain, and fibromyalgia. The novel gliotoxin analog compound acts by acting as an antagonist to one or more opioid receptors, which, when present leads to the inhibition of conditions, providing increased performance over known treatments. The disclosed compounds also shows the ability to cross the blood-brain-barrier in a highly efficient manner.
NOVEL SELECTIVE KAPPA OPIOID RECEPTOR ANTAGONISTS AND METHODS RELATED THERETO FOR TREATMENT OF ADDICTION AND NEUROPATHIC PAIN
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Paragraph 00073, (2020/05/28)
Disclosed is a composition and method for a therapeutic treatment that is able to combat certain conditions such as addiction, alcohol dependence, opioid abuse treatment, neurological disorders, neuropathic pain, and combinations thereof. The compounds act by acting as selective antagonist to the kappa (K) opioid receptor, which, when present leads to the inhibition of conditions, providing increased performance over known treatments. The disclosed compounds also shows the ability to cross the blood-brain-barrier in a highly efficient manner. The disclosed compounds are shown to be effective in the nanomolar range.
Enantio- and Diastereoselective Synthesis of β-Aryl-β-pyrazolyl α-Amino Acid Esters via Copper-Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones
Gong, Yan-Chuan,Wang, Yue,Li, Er-Qing,Cui, Hao,Duan, Zheng
supporting information, (2019/02/07)
A fully stereoselective synthesis of unnatural chiral β-aryl-β-pyrazolyl α-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded β-1H-pyrazol-5-ol-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.
Enantio- And diastereoselective synthesis of b-Aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed reaction of azomethine ylides with benzylidenepyrazolones
Gong, Yan-Chuan,Wang, Yue,Li, Er-Qing,Cui, Hao,Duan, Zheng
supporting information, p. 1389 - 1393 (2019/10/28)
A fully stereoselective synthesis of unnatural chiral b-aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded b-1H-pyrazol-5-ol-a-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.
Preparation method of 3 -chloro-5-trifluoromethyl-2-pYRidine methylamine salt
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Paragraph 0020; 0021, (2019/04/26)
The invention discloses a preparation method of 3 -chloro-5-trifluoromethyl-2-pYRidine methylamine salt, and the compound is mainly used as an intermediate compound for synthesis of bactericide fluopicolide for preventing and treating diseases caused by oomycete pathogenic bacteria. According to the preparation method, intermediate compounds of all the steps are prepared by intermittent step-by-step reaction, the finally obtained 3 -chloro-5-trifluoromethyl-2-pYRidine methylamine salt compound is reacted with 2, 6-dichlorobenzoyl chloride in the presence of an organic amine and a solvent to prepare the final object fluopicolide; and nucleophilic substitution reaction, imine hydrolysis and decarboxylation reaction are performed in the preparation process to obtain the target product, the reaction conditions are mild, the operation is simple, and the method is relatively suitable for industrial production.
A Manufacturing Process to an Intermediate in the Synthesis of Acalabrutinib
Chen, Bo,Golden, Michael,Li, Zhonglian,Xu, Liwen,Xu, Zhaofu,Yao, Xiaolong
, p. 1458 - 1460 (2018/10/15)
Optimization and application of the reported synthesis of (3-chloropyrazin-2-yl)methanamine 3 have provided a high yielding, fully telescoped procedure to key intermediate 5 in the synthesis of acalabrutinib.
2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
Guerrero-Corella, Andrea,Esteban, Francisco,Iniesta, Manuel,Martín-Somer, Ana,Parra, Mario,Díaz-Tendero, Sergio,Fraile, Alberto,Alemán, Jose
supporting information, p. 5350 - 5354 (2018/04/19)
An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ-diamino acid derivatives with excellent stereoselectivity.