116911-32-1Relevant articles and documents
A convenient synthesis of azido peptides by post-assembly diazo transfer on the solid phase applicable to large peptides
Rijkers, Dirk T.S.,Van Vugt, H.H.Ricardo,Jacobs, Hans J.F.,Liskamp, Rob M.J.
, p. 3657 - 3660 (2002)
An efficient method for the conversion of solid phase bound peptide amines into azides by a diazo transfer using triflyl azide in the presence of divalent copper ions is described. α-Azido acids and azido peptides - up to 30 amino acids in length - are obtained in good yields and high purities after cleavage from the solid support.
Design, Synthesis, and Activity Evaluation of Stereoconfigured Tartarate Derivatives as Potential Anti-inflammatory Agents in Vitro and in Vivo
Kumari, Priya,Singh, Palwinder,Kaur, Jashanpreet,Bhatti, Rajbir
, p. 9550 - 9566 (2021)
Preclinical and clinical data reveal that inflammation is strongly correlated with the pathogenesis of a number of diseases including those of cancer, Alzheimer, and diabetes. The inflammatory cascade involves a multitude of cytokines ending ultimately with the activation of COX-2/LOX for the production of prostaglandins and leukotrienes. While the available inhibitors for these enzymes suffer from nonoptimal selectivity, in particular for COX-2, we present here the results of purposely designed tartarate derivatives that exhibit favorable selectivity and significant effectiveness against COX-2 and LOX. Integrated approaches of molecular simulation, organic synthesis, and biochemical/physical experiments identified 15 inhibiting COX-2 and LOX with respective IC50 4 and 7 nM. At a dose of 5 mg kg-1 to Swiss albino mice, 15 reversed algesia by 65% and inflammation by 33% in 2-3 h. We find good agreement between experiments and simulations and use the simulations to rationalize our observations.
Concise synthesis of: N -phosphorylated amides through three-component reactions
Yang, Shang-Dong,Zhang, Tao,Zhou, Linlin,Zhu, Yuan-Yuan
supporting information, p. 9417 - 9421 (2021/12/09)
N-Phosphorylated amides continue to be an unparalleled asset for the development of pharmaceutical molecules, and the importance of this framework has inspired researchers to look for concise and efficient methods for the synthesis of this unit. In this work, a new strategy was developed in which a one-pot synthesis of N-phosphorylated amides was achieved by a three-component reaction with carboxylic acids, phosphorus chlorides and azides under mild reaction conditions. To our knowledge, this is the first study in which this framework was constructed through a multicomponent reaction, which is innovative, efficient and economical. This journal is
Glycerol conversion to high-value chemicals: The implication of unnatural α-amino acid syntheses using natural resources
Park, Yun Ji,Yang, Jung Woon
, p. 2615 - 2620 (2019/06/03)
Glycerol derivatives are an important class of compounds, which have great applications as basic structural building blocks in organic synthesis. O-Benzylglycerol was oxidised to produce a high-value compound in high yield using a NaOtBu-O2 system. Furthermore, the synthetic utility of the resulting product was demonstrated by its transformation into unnatural α-amino acids, thus showing the valorisation of glycerol biomass.
Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring
Kumari, Santosh,Joshi, Sunita,Shakoor, S.M. Abdul,Agarwal, Devesh S.,Panda, Siva S.,Pant, Debi D.,Sakhuja, Rajeev
, p. 1415 - 1426 (2015/09/15)
Fluorophores based on 4-triazolyl, 7-hydroxy-4-triazolylmethyl, 4-O-triazolylmethyl, and 7-O-triazolylmethyl coumaryl-tagged amino acids and dipeptides were synthesized by copper-catalyzed [3+2] cycloaddition reaction between azido- or alkynyl-functionalized coumarins with alkynyl- or azido-functionalized amino acid and dipeptides in good-to-excellent yields. Steady-state absorption and the fluorescence properties of the synthesized conjugates were studied. The chemical applicability of these amino acid and peptide-based fluorophores was successfully demonstrated by their linear elongation by further tagging them with appropriate C- or N-terminus amino acid.
SELECTIVE HISTONE DEACETYLASE 8 INHIBITORS
-
Paragraph 00270, (2014/08/07)
Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of histone deacetylase 8 (HDAC8). Also described herein are methods of using such HDAC8 inhibitors, alone and in combination with other co
A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
Kitamura, Mitsuru,Kato, So,Yano, Masakazu,Tashiro, Norifumi,Shiratake, Yuichiro,Sando, Mitsuyoshi,Okauchi, Tatsuo
, p. 4397 - 4406 (2014/06/23)
Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.
A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on 'clicked' pseudo-glycopeptides
Yang, Jin-Wei,He, Xiao-Peng,Li, Cui,Gao, Li-Xin,Sheng, Li,Xie, Juan,Shi, Xiao-Xin,Tang, Yun,Li, Jia,Chen, Guo-Rong
supporting information; experimental part, p. 1092 - 1096 (2011/04/16)
There has been considerable interest in the development of protein tyrosine phosphatase (PTP) inhibitors since many of the PTP members are tightly associated with major human diseases including autoimmune disorders, diabetes and cancer. We report here a u
1,2,3-Triazolyl amino acids as AMPA receptor ligands
Stanley,Pedersen, D. Sejer,Nielsen,Kvist,Mathiesen,Br?uner-Osborne,Taylor,Abell
supporting information; experimental part, p. 7512 - 7515 (2011/03/17)
The central nervous system glutamate receptors are an important target for drug discovery. Herein we report initial investigations into the synthesis and glutamate receptor activity of 1,2,3-triazolyl amino acids. Two compounds were found to be selective
One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehydes and amines
Maisonneuve, Stephane,Xie, Juan
experimental part, p. 2977 - 2981 (2010/01/21)
A one-pot, three-step synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehyde and amine has been developed by in situ transformation of aldehyde into alkyne, followed by diazo-transfer of amine into azide and subsequent cycloaddition. This procedure allowed the synthesis of fluorescent amino acid derivatives as well as glycoconjugate mimetics. Georg Thieme Verlag Stuttgart.