94779-07-4Relevant academic research and scientific papers
Functionalization of Sulfonamide-Containing Peptides through Late-Stage Palladium-Catalyzed C(sp3)-H Arylation
Bai, Qingqing,Tang, Jian,Wang, Huan
supporting information, p. 5858 - 5861 (2019/08/27)
Bioactive peptides are emerging as promising candidates of clinic therapeutics. Here, we report a method for late-stage functionalization of sulfonamide-containing peptides through Pd-catalyzed C(sp3)-H arylation. In this protocol, the backbone
Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents
Suhas, Ramesh,Channe Gowda, Dase
experimental part, p. 850 - 862 (2012/06/04)
A series of new aurantiamide acetate analogues were synthesized by modifying its N-terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti-inflammatory activity against carrageenan-induced oedema in albino rats at different doses (25, 50 and 100mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.
Design and synthesis of tryptophan containing peptides as potential analgesic and anti-inflammatory agents
Suhas,Gowda, D.Channe
scheme or table, p. 535 - 540 (2012/09/22)
A new series of smaller peptides with tryptophan at C-terminal and varying N-protected amino acids/peptides were designed, synthesized and characterized by analytical and spectroscopic techniques. Analgesic and anti-inflammatory properties of these peptides were carried out in vivo using tail-flick method and carrageenan-induced paw edema method, respectively, at different doses and different time intervals. Most of the peptides synthesized displayed enhanced activity, and particularly tetra and hexapeptides 29-31 were found to be even more potent than the reference standards used. Moreover, some peptides have exhibited promising activity even after 24h of administration, whereas the reference standards were active only up to 3h. Further, the compounds did not present any ulcerogenic liability.
Stereoselective and N-terminal selective α-alkylation of peptides using a pyridoxal model compound as a chiral N-terminal activator
Miyashita, Kazuyuki,Iwaki, Hiroshi,Tai, Kuninori,Murafuji, Hidenobu,Imanishi, Takeshi
, p. 1987 - 1988 (2007/10/03)
Stereoselective and N-terminal selective α-alkylation of peptides is achieved using a pyridoxal model compound as an N-terminal activator which also functions as a chiral auxiliary.
Sugar Amino Acids and Sugar Peptides by Triflate Substitution
Kowollik, Wolfgang,Janairo, Gerardo,Voelter, Wolfgang
, p. 427 - 432 (2007/10/02)
Benzyl 2,3-anhydro-4-O-triflyl-β-L-ribopyranoside (1) reacts with L-alanine benzyl ester (2), L-phenylalanylglycine benzyl ester (4), and 4-aminobenzoic acid tert-butyl ester (6), with inversion at C-4 and formation of a C - N bond between the sugar and t
The Steric Hindrance of the Stepwise Reaction of N-Carboxy α-Amino Acid Anhydride with the α-Amino Acid Ester
Oya, Masanao,Takahashi, Tomoko
, p. 2705 - 2707 (2007/10/02)
The mechanisms of the reactions of 4-alkyloxazolidinediones (1) (N-carboxy α-amino acid anhydrides(NCAs)) with α-amino acid benzyl ester p-toluenesulfonates (2) were investigated in acetonitrile containing triethylamine at low and room temperatures.Two types of reactions were observed: (1) the polymerization of NCAs was initiated with a small amount of 2 to produce polypeptides (6), and (2) the dipeptide benzyl esters (4) were produced by the stepwise reaction of NCAs with the esters.Both the polymerization and the dipeptide formation (1+2) seemed to be initiated by the nucleophilic attack of the amino group of the ester on the C-5 carbon of NCAs.The polymerization proceeded when the side chains of the amino acid esters (R2) were more bulky than those of the NCAs (R1).On the contrary, dipeptide esters were produced when the side chains of the NCAs (R1) were more bulky than those of the esters (R2).
