57105-50-7Relevant articles and documents
Design, synthesis and characterization of HIV-1 ca-targeting small molecules: Conformational restriction of PF74
Sahani, Rajkumar Lalji,Diana-Rivero, Raquel,Vernekar, Sanjeev Kumar V.,Wang, Lei,Du, Haijuan,Zhang, Huanchun,Castaner, Andres Emanuelli,Casey, Mary C.,Kirby, Karen A.,Tedbury, Philip R.,Xie, Jiashu,Sarafianos, Stefan G.,Wang, Zhengqiang
, (2021/05/24)
Small molecules targeting the PF74 binding site of the HIV-1 capsid protein (CA) confer potent and mechanistically unique antiviral activities. Structural modifications of PF74 could further the understanding of ligand binding modes, diversify ligand chemical classes, and allow identification of new variants with balanced antiviral activity and metabolic stability. In the current work, we designed and synthesized three series of PF74-like analogs featuring conformational constraints at the aniline terminus or the phenylalanine carboxamide moiety, and characterized them using a biophysical thermal shift assay (TSA), cell-based antiviral and cytotoxicity assays, and in vitro metabolic stability assays in human and mouse liver microsomes. These studies showed that the two series with the phenylalanine carboxamide moiety replaced by a pyridine or imidazole ring can provide viable hits. Subsequent SAR identified an improved analog 15 which effectively inhibited HIV-1 (EC50 = 0.31 μM), strongly stabilized CA hexamer (?Tm = 8.7?C), and exhibited substantially enhanced metabolic stability (t1/2 = 27 min for 15 vs. 0.7 min for PF74). Metabolic profiles from the microsomal stability assay also indicate that blocking the C5 position of the indole ring could lead to increased resistance to oxidative metabolism.
Preparation of synthetic auxin-amino acid conjugates
Revelou, Panagiota-Kyriaki,Constantinou-Kokotou, Violetta
, p. 1708 - 1712 (2019/05/15)
Auxin amide conjugates are regulators of the most important auxin, indole-3-acetic acid (IAA), which is considered responsible for many important processes within the plants. Herein, amide conjugates of IAA were synthesized employing a simple and efficient coupling method with WSCI·HCl, a water-soluble condensing reagent, in the presence of 1-hydroxybenzotriazole. IAA conjugates with 10 amino acids along with their corresponding methyl esters were prepared in excellent yields, up to 95%, aiming to facilitate their identification in plant species. Eight IAA-amino acid methyl ester conjugates are characterized here for the first time.
Syntheses of IAA- and IPA-amino acid conjugates
Katritzky, Alan R.,Khelashvili, Levan,Munawar, Ali
supporting information; experimental part, p. 9171 - 9173 (2009/04/11)
(Chemical Equation Presented) Amino acid derivatives of IAA and IPA are prepared conveniently and efficiently by coupling of readily available 2a-b with diverse free amino acids 3a-g and (3c+3c′) to give compounds 4a-j, (4c+4c′) and (4h+4h′) in 38-70% yie
