71273-81-9Relevant academic research and scientific papers
POLYMER BOUND EDC (P-EDC): A CONVENIENT REAGENT FOR FORMATION OF AN AMIDE BOND
Desai, Manoj C.,Stramiello, Linda M. Stephens
, p. 7685 - 7688 (1993)
A facile preparation of polymer bound 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (P-EDC) from commercially available starting materials is described.The P-EDC was found to be a convenient and general reagent for coupling of a variety of amines with diverse carboxylic acids.
Selective sensing of sulfate anions in water with cyclopeptide-decorated gold nanoparticles
Bartl, Julia,Koch, Marcus,Kubik, Stefan,Reinke, Lena
supporting information, p. 10457 - 10460 (2020/10/02)
The interaction of cyclopeptides bound to the surface of mixed monolayer-protected gold nanoparticles with sulfate anions causes the crosslinking and concomitant precipitation of the nanoparticles from aqueous solutions even in presence of an excess of competing anions, thus allowing the naked eye detection of sulfate in water.
Methylene C(sp3)-H β,β′-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand
Bull, James A.,St John-Campbell, Sahra,White, Andrew J. P.
supporting information, (2020/03/10)
A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The amide N-substituents are shown to affect yield and can enhance the rate of arylation compared with the α-amino acid. Addition of a pyridone ligand further enhanced reactivity. The reaction is successful for a range of aryl iodides, and various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. A mechanism is proposed evoking a transient enamine.
A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids
Fatemi, Solmaz,Gernigon, Nicolas,Hall, Dennis G.
, p. 4016 - 4028 (2015/07/15)
The development of direct and atom-economical amidation methods is of high priority because of the importance of amides and peptides as components of pharmaceuticals and commodity chemicals. This article describes the identification of more economical and more practical conditions for direct amidation of carboxylic acids and amines using the MIBA catalyst (5-methoxy-2-iodophenylboronic acid, 6) and its application to the coupling of α- and β-amino acid derivatives. It is now possible to use half of the quantity of molecular sieves prescribed in the original procedure, at a higher concentration leading to a reduction of waste and a substantially improved E-factor. This procedure was validated in the multigram scale preparation of prototypical amides, including aminoacids, using toluene as the solvent. Because of substrate inhibition of the catalyst with monoprotected α-aminoacids, the use of doubly-protected N-phthaloyl α-aminoacids or α-azidoacids is required in order to produce dipeptide products in moderate yields. β-Aminoacids do not suffer from this problem, and Boc-β-aminoacids can be coupled successfully. Unlike other boronic acid catalysts, 6 is active under ambient and low-heat conditions, which helps prevent any epimerization of chiral α-aminoacid derivatives.
Sulfur incorporation generally improves Ricin inhibition in pterin-appended glycine-phenylalanine dipeptide mimics
Wiget, Paul A.,Manzano, Lawrence A.,Pruet, Jeff M.,Gao, Grace,Saito, Ryota,Monzingo, Arthur F.,Jasheway, Karl R.,Robertus, Jon D.,Anslyn, Eric V.
supporting information, p. 6799 - 6804 (2014/01/06)
Several 7-aminoamido-pterins were synthesized to evaluate the electronic and biochemical subtleties observed in the 'linker space' when N-{N-(pterin-7-yl)carbonylglycyl}-l-phenylalanine 1 was bound to the active site of RTA. The gylcine-phenylalanine dipeptide analogs included both amides and thioamides. Decarboxy gly-phe analog 2 showed a 6.4-fold decrease in potency (IC50 = 128 μM), yet the analogous thioamide 7 recovered the lost activity and performed similarly to the parent inhibitor (IC50 = 29 μM). Thiourea 12 exhibited an IC50 nearly six times lower than the oxo analog 13. All inhibitors showed the pterin head-group firmly bound in their X-ray structures yet the pendants were not fully resolved suggesting that all pendants are not firmly bound in the RTA linker space. Calculated log P values do not correlate to the increase in bioactivity suggesting other factors dominate.
BORONIC ACID CATALYSTS AND METHODS OF USE THEREOF FOR ACTIVATION AND TRANSFORMATION OF CARBOXYLIC ACIDS
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Page/Page column 41, (2012/09/10)
The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III:
NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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, (2009/10/31)
The embodiments provide compounds of the general Formulae I, II, III, IV, V, VI, VII, and X, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.
2-[3-[2-[(25)-2-cyano-1-pyrrolidinyl]-2-oxoethylamino]-3-methyl-1-oxobutyl] -1,2,3,4-tetrahydroisoquinoline: A potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV
Tsu, Hsu,Chen, Xin,Chen, Chiung-Tong,Lee, Shiow-Ju,Chang, Chung-Nien,Kao, Kuo-His,Coumar, Mohane Selvaraj,Yeh, Yen-Ting,Chien, Chia-Hui,Wang, Hsin-Sheng,Lin, Ke-Ta,Chang, Ying-Ying,Wu, Ssu-Hui,Chen, Yuan-Shou,Lu, I.-Lin,Wu, Su-Ying,Tsai, Ting-Yueh,Chen, Wei-Cheng,Hsieh, Hsing-Pang,Chao, Yu-Sheng,Jiaang, Weir-Torn
, p. 373 - 380 (2007/10/03)
Dipeptidyl peptidase IV (DPP-IV) inhibitors are expected to become a new type of antidiabetic drugs. Most known DPP-IV inhibitors often resemble the dipeptide cleavage products, with a proline mimic at the P1 site. As off-target inhibitions of DPP8 and/or DPP9 have shown profound toxicities in the in vivo studies, it is important to develop selective DPP-IV inhibitors for clinical usage. To achieve this, a new class of 2-[3-[[2-[(2S)-2-cyano-1-pyrrolidinyl]-2- oxoethyl]amino]-1-oxopropyl]-based DPP-IV inhibitors was synthesized. SAR studies resulted in a number of DPP-IV inhibitors, having IC50 values of 50 > 100 μM) and DPP-II (IC50 > 30 μM). Compound 21a suppressed the blood glucose elevation after an oral glucose challenge in Wistar rats and also inhibited plasma DPP-IV activity for up to 4 h in BALB/c mice. The results show that compound 21a possesses in vitro and in vivo activities comparable to those of NVP-LAF237 (4), which is in clinical development. 2006 American Chemical Society.
Pyrazolobenzamides and derivatives as factor Xa inhibitors
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Page/Page column 84-85, (2010/11/08)
The present application describes pyrazolobenzamides and derivatives thereof of Formula I: [in-line-formulae]P4-P-M-M4??I [/in-line-formulae] or pharmaceutically acceptable salt forms thereof. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.
Urethane N-carboxyanhydrides from β-amino acids
McKiernan,Huck,Fehrentz,Roumestant,Viallefont,Martinez
, p. 6541 - 6544 (2007/10/03)
A general method has been developed for the synthesis of N-tert-butyloxycarbonyl N-carboxyanhydrides from β-amino acids using Vilsmeier complex. These β-UNCA are stable, and the reactivity with different nucleophiles (alcohol, amine, lithium enolate) was studied.
