173306-82-6Relevant academic research and scientific papers
Stereoselective, nonracemic synthesis of ω-borono-α-amino acids
Collet, Sylvain,Bauchat, Patrick,Danion-Bougot, Renee,Danion, Daniel
, p. 2121 - 2131 (1998)
ω-Unsaturated α-amino acids are synthesized through condensation of allyl and propargyl bromides or of 9-bromoundecene with a Ni(II) complex of the Schiff base derived from glycine and BPB. Hydroboration with Ipc2BH followed by oxidation with acetaldehyde affords enantiomerically pure ω- borono-α-aminocarboxylic acids.
The synthesis of [4-carboranylalanine,5-leucine]-enkephalin
Fauchere,Leukart,Eberle,Schwyzer
, p. 1385 - 1395 (1979)
The title compound, an analogue of [Leu5]-enkephalin with L-O-carboranylalanine replacing L-phenylalanine in position 4, was prepared by fragment condensation. The analogue has a 3-fold higher affinity for rat brain opiate receptors in the [3H]naloxone competition assay than natural [Leu5]-enkephalin. Like [Leu5]-enkephalin and Na-acetyl-[Leu5]-enkephalin, the N-terminal tripeptide fragment, H Tyr-Gly-Gly OH, had no melanotropic activity in the Rana pipiens frog skin assay. A convenient, direct synthesis of methyl t-butoxycarbonyl-L-o-carboranylalaninate from methyl t-butoxycarbonyl-L-propargylglycinate is described, and the 13C-NMR, spectra of L-O-carboranylalanine recorded. The procedure was extended to the preparation of BOC Car-Leu OMe from BOC Pra-Leu OMe. A number of new propargylglycine derivatives are reported.
Sonogashira Reaction of Bromofluoropyridinaldoxime Nuclei: Convergent Synthesis of Functionalized 2- and 3-Fluoropyridine Scaffolds
Yerri, Jagadeesh,Baati, Rachid
, p. 4161 - 4165 (2018)
A chemoselective palladium catalyzed Sonogashira cross-coupling of bromofluoropyridinaldoxime with highly functionalized alkynes is presented. This reaction is fully compatible with unprotected sensitive aldoxime and affords representative underexplored new scaffolds. The process exhibits a broad scope of alkynes, dialkynes, and large functional group compatibility, including the use of non-radioactive isotopic reporter such as 15N labeled oxime and chiral substrates.
Stable cyclopropene-containing analogs of the amino acid neurotransmitter glutamate
Kumar, Pratik,Huang, Wei,Shukhman, David,Camarda, Frank M.,Laughlin, Scott T.
, p. 1476 - 1480 (2019)
As a neurotransmitter, the amino acid glutamate has been the subject of efforts to generate structural analogs with unique properties. Here we report a practical, half-gram synthesis of two cyclopropene-containing glutamate analogs. These analogs are stable in solution, in the presence of the biological nucleophile glutathione, upon concentration, and during long-term storage, while maintaining their amenability to photo- or enzyme-caging and reactivity with bioorthogonal reaction partners like s-tetrazine or light-activated tetrazoles.
Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes
Birepinte, Mélodie,Champagne, Pier Alexandre,Paquin, Jean-Fran?ois
supporting information, (2021/11/30)
A photoinitiated anti-hydropentafluorosulfanylation of terminal alkynes using SF5Cl and (TMS)3SiH as the hydrogen atom donor is reported. This transformation generates selectively (Z)-(1-alken-1-yl)pentafluoro-λ6-sulfanes
6-SUBSTITUTED 3-FLUORO-2-PYRIDINALDOXIME, 3-FLUORO-2-PYRIDINE HYDROXAMIC ACID, AND 3-FLUORO-2-PYRIDINAMIDOXIME SCAFFOLDS
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Paragraph 0045; 0109; 0110, (2019/05/04)
The present invention relates to a compound of formula (I), as well as to a process for preparing the compounds of formula (I) by a chemoselective Sonogashira reaction. It also relates to a pharmaceutical composition comprising at least one compound of formula (I) and at least one pharmaceutically acceptable support. Finally, it relates to the use of such a compound as a medicine, preferably in the treatment of a nervous and/or respiratory failure due to intoxication with at least one organophosphorous nerve agent; in the treatment of neurological diseases such as Alzheimer's disease; and/or in the treatment of cancer; and/or for use as antiviral drug.
Design, synthesis and biological evaluation of C(4) substituted monobactams as antibacterial agents against multidrug-resistant Gram-negative bacteria
Kou, Qunhuan,Wang, Ting,Zou, Feng,Zhang, Shuhua,Chen, Qian,Yang, Yushe
, p. 98 - 109 (2018/04/05)
A series of novel pyridone conjugated monobactams with various substituents at the (4) position were synthesized and evaluated for their antibacterial activities against a panel of multidrug-resistant (MDR) Gram-negative bacteria in vitro. Compounds 46d, 54 and 75e displayed good to moderate activities against P. aeruginosa, among which the activity of 75e against P. aeruginosa was comparable to that of BAL30072 under iron limitation condition. Compounds 35, 46d, 54, 56a, 56c and 56d exhibited good to excellent antibacterial activities against E. coli and K. pneumoniae, which were comparable or superior to that of BAL30072. In vitro liver microsomal stability was further evaluated and the results manifested that Compounds 35, 46d and 54 were metabolically stable in human liver microsomes.
Ligand-Enabled Alkynylation of C(sp3)?H Bonds with Palladium(II) Catalysts
Fu, Haiyan,Shen, Peng-Xiang,He, Jian,Zhang, Fanglin,Li, Suhua,Wang, Peng,Liu, Tao,Yu, Jin-Quan
, p. 1873 - 1876 (2017/02/05)
The palladium(II)-catalyzed β- and γ-alkynylation of amide C(sp3)?H bonds is enabled by pyridine-based ligands. This alkynylation reaction is compatible with substrates containing α-tertiary or α-quaternary carbon centers. The β-methylene C(sp
Gold-Catalyzed Cycloisomerization of Alkyne-Containing Amino Acids: Controlled Tuning of C–N vs. C–O Reactivity
Medran, Noelia S.,Villalba, Matías,Mata, Ernesto G.,Testero, Sebastián A.
, p. 3757 - 3764 (2016/08/16)
Versatile alkyne-containing amino acids were used as ambident precursors in the divergent synthesis of alkylidenelactones and 1-pyrrolines. Two gold-catalyzed protocols were applied for selective intramolecular O- and N-cycloisomerization reactions.
α-Propargyl amino acid-derived optically active novel substituted polyacetylenes: Synthesis, secondary structures, and responsiveness to ions
Sogawa, Hiromitsu,Shiotsuki, Masashi,Sanda, Fumio
experimental part, p. 2008 - 2018 (2012/07/13)
Novel optically active substituted acetylenes HCi￡ CCH 2CR1(CO2CH3)NHR2 [(S)-/(R)-1: R1 = H, R2 = Boc, (S)-2: R1 = CH3, R2 = Boc, (S)-3: R1 = H, R2 = Fmoc, (S)-4: R1 = CH3, R2 = Fmoc (Boc = tert-butoxycarbonyl, Fmoc = 9-fluorenylmethoxycarbonyl)] were synthesized from α-propargylglycine and α-propargylalanine, and polymerized with a rhodium catalyst to provide the polymers with number-average molecular weights of 2400-38,900 in good yields. Polarimetric, circular dichroism (CD), and UV-vis spectroscopic analyses indicated that poly[(S)-1], poly[(R)-1], and poly[(S)-4] formed predominantly one-handed helical structures both in polar and nonpolar solvents. Poly[(S)-1a] carrying unprotected carboxy groups was obtained by alkaline hydrolysis of poly[(S)-1], and poly[(S)-4b] carrying unprotected amino groups was obtained by removal of Fmoc groups of poly[(S)-4] using piperidine. Poly[(S)-1a] and poly[(S)-4b] also exhibited clear CD signals, which were different from those of the precursors, poly[(S)-1] and poly[(S)-4]. The solution-state IR measurement revealed the presence of intramolecular hydrogen bonding between the carbamate groups of poly[(S)-1] and poly[(S)-1a]. The plus CD signal of poly[(S)-1a] turned into minus one on addition of alkali hydroxides and tetrabutylammonium fluoride, accompanying the red-shift of λmax. The degree of λmax shift became large as the size of cation of the additive.
