541-46-8Relevant academic research and scientific papers
MODIFIED PEPTIDES AND THEIR USE
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Paragraph 0081; 0084; 0099-0100, (2020/05/13)
The invention relates to a compound of formula (A) wherein n is an integer from 1 to 6, and R1, R1', R2, R2', R3, R3' are cationic or hydrophobic residues.
Tailoring the Physicochemical Properties of Antimicrobial Peptides onto a Thiazole-Based γ-Peptide Foldamer
Bonnel, Clément,Legrand, Baptiste,Simon, Matthieu,Clavié, Margaux,Masnou, Agnès,Jumas-Bilak, Estelle,Kang, Young Kee,Licznar-Fajardo, Patricia,Maillard, Ludovic T.,Masurier, Nicolas
, p. 9168 - 9180 (2020/10/19)
Antimicrobial peptides (AMPs) are amphipathic molecules displaying broad-spectrum bactericidal activity, providing opportunities to develop a new generation of antibiotics. However, their use is limited either by poor metabolic stability or by high hemolytic activity. We herein addressed the potential of thiazole-based γ-peptide oligomers named ATCs as tunable scaffolds to design polycationic AMP mimetics. Knowing the side chain distribution along the backbone, we rationally designed facially amphiphilic sequences with bactericidal effect in the micromolar range. Since no hemolytic activity was detected up to 100 μM, this class of compounds has shown the potential for therapeutic development.
Appraisal of Ruthenium(II)complexes of (4-phenoxyphenylazo)ligands for the synthesis of primary amides by dint of hydroxylamine hydrochloride and aldehydes
Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Sounthararajan, Muniyan,Sakthi, Dharmalingam,Bharathi, Kuppannan Shanmuga
, p. 67 - 77 (2019/05/22)
A new family of O, N donor-functionalized (4-phenoxyphenylazo)-2-naphthol/4-substituted phenol-based ligands (HL1-HL4)has been synthesized. The prepared ligands were successfully utilized for the access of a series of ruthenium(II)carbonyl complexes of the type [Ru(L)Cl(CO)(EPh3)3](E = phosphine/arsine), (L = 1-(4-phenoxyphenylazo)-2-naphthol (HL1), 2-(4-phenoxyphenylazo)-4-chlorophenol (HL2), 2-(4-phenoxyphenylazo)-4-methylphenol (HL3)and 2-(4-phenoxyphenylazo)-4-methoxyphenol (HL4)). All of the ruthenium(II)carbonyl complexes and ligands have been fully characterized by FT-IR, UV–visible, 1H NMR, 31P NMR, mass spectrometry and CHN analysis. The ligands have been analyzed by 13C NMR. The UV–visible spectroscopic study reveals that both the ligands and Ru(II)complexes exhibit excellent charge transfer transitions. This is the basic criteria for the oxidative amidation reaction, which is an influential strategy for the transformation of oxygenated organic compounds to the profitable amides. However, this catalytic process makes more impact on the application of new divalent ruthenium(II)azo compounds as catalyst in a single-pot conversion of aldehydes to amides in the presence of NaHCO3.
A selective hydration of nitriles catalysed by a Pd(OAc)2-based system in water
Sanz Sharley, Daniel D.,Williams, Jonathan M.J.
supporting information, p. 4090 - 4093 (2017/09/27)
In situ formation of a [Pd(OAc)2bipy] (bipy = 2,2′-bipyridyl) complex in water selectively catalyses the hydration of a wide range of organonitriles at 70 °C. Catalyst loadings of 5 mol% afford primary amide products in excellent yields in the absence of hydration-promoting additives such as oximes and hydroxylamines.
Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation
Gille, Franziska,Kirschning, Andreas
supporting information, p. 564 - 570 (2016/04/08)
The preparation of peptide fragments containing dehydrovaline and dehydroisoleucine moieties present in the antibiotic myxovalargin is reported. Peptide formation is based on a copper-mediated C-N cross-coupling protocol between an acyl amide and a peptidic vinyl iodide. The presence of a neighboring arginine in the vinyl iodide posed a challenge with respect to the choice of the protecting group and the reaction conditions. It was found that ornithine - a suitable precursor - is better suited than arginine for achieving good yields for the C-N cross-coupling reaction. The optimized conditions were utilized for the synthesis of peptides 32, 33, 39 and 40 containing a neighboring ornithine as well as for the tripeptide 44 containing dehydroisoleucine with the correct stereochemistry.
Au/Ag-cocatalyzed aldoximes to amides rearrangement under solvent- and acid-free conditions
Ramon, Ruben S.,Bosson, Johann,Diez-Gonzalez, Silvia,Marion, Nicolas,Nolan, Steven P.
experimental part, p. 1197 - 1202 (2010/04/02)
(Chemical Equation Presented) The gold/silver-cocatalyzed conversion of aldoximes into primary amides is reported. The reaction, which proceeds under neat and acid-free conditions, allows for the conversion of a range of aldoximes, and is a rare example of cooperative catalysis involving well-defined gold species.
Chemical synthesis and biological evaluation of palmerolide A analogues
Nicolaou,Leung, Gulice Y. C.,Dethe, Dattatraya H.,Guduru, Ramakrishna,Sun, Ya-Ping,Chek, Shik Lim,Chen, David Y.-K.
body text, p. 10019 - 10023 (2009/02/04)
Molecular design and chemical synthesis of several palmerolide A analogues allowed the first structure activity relationships (SARs) of this newly discovered marine antitumor agent. From several analogues synthesized and tested (ent-1, 5-14, 21-26, 50, 51), compounds 25 (with a phenyl substituent on the side chain) and 51 (lacking the C-7 hydroxyl group) were the most interesting, exhibiting approximately a 10-fold increase in potency and equipotency, respectively, to the natural product. These findings point the way to more focused structure activity relationship studies.
Mild oxidative one-carbon homologation of aldehyde to amide
Bonne, Damien,Dekhane, Mouloud,Zhu, Jieping
, p. 6926 - 6927 (2007/10/03)
One-carbon homologation of aldehyde into amide is realized in one-pot by its reaction with potassium α-p-methoxyphenyl-α-isocyano acetic acid (1c) and hydrochloride salt of dimethylamine (3a) in toluene at room temperature followed by acidic workup. In this multicomponent reaction, 1c served as donor of the CONH2 function to aldehyde, while the dimethylamine acted as a shuttle molecule to initiate/terminate the sequence and to mediate the internal redox process of one of the three-component adducts. Ready accessibility, nominal cost of the reagents, and mild conditions are attractive features of the present method. Copyright
RENIN INHIBITING PEPTIDES HAVING AN ALPHA-HETEROATOM AMINO ACID AT THE P3 POSITION
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, (2008/06/13)
The invention concerns novel renin-inhibitory compounds which are useful for treating renin-associated hypertension, congestive heart failure, hyperaldosteronism, glaucoma, and diseases caused by retroviruses including HTLV-I-II, and-III. Processes for preparing the compounds, novel intermediates useful in the preparation thereof, compositions containing them, and methods of using them are included. Also included is a diagnostic method which uses the compounds to determine the presence of renin-associated hypertension, congestive heart failure, or hyperaldosteronism.
Free Radical Substitution. Part 38. The Effect of Solvent on the Atomic Chlorination and Bromination of 2-Substituted Butanes and the Importance of Steric Effects
Atto, Saeed Y.,Tedder, John M.,Walton, John C.
, p. 629 - 634 (2007/10/02)
The relative selectivity of atomic halogenation of 2-substituted butanes is influenced by the phase and by solvents.There are solvents which increase the selectivity compared with the gas phase and solvents which decrease the relative selectivity.However the most striking feature of the halogenation (especially the bromination) of 2-substituted butanes is the high reactivity of the 2-position notwithstanding very unfavourable polar effects.This reactivity is attributed to the release of steric compression associated with the abstraction of the tertiary hydrogen atom.The halogenation of butan-2-ol esters is associated with some decomposition of 2-butyl radical (OCOR)CH3> and the chlorination of 2-phenylbutane with the formation of olefins 2-phenylbut -1-ene and 2-phenylbut-2-ene.
