23776-87-6Relevant academic research and scientific papers
Efficient Amino-Sulfhydryl Stapling on Peptides and Proteins Using Bifunctional NHS-Activated Acrylamides
Silva, Maria J. S. A.,Faustino, Hélio,Coelho, Jaime A. S.,Pinto, Maria V.,Fernandes, Adelaide,Compa?ón, Ismael,Corzana, Francisco,Gasser, Gilles,Gois, Pedro M. P.
, p. 10850 - 10857 (2021)
Widely used reagents in the peptide functionalization toolbox, Michael acceptors and N-hydroxysuccinimide (NHS) activated esters, are combined in NHS-activated acrylamides for efficient chemoselective amino-sulfhydryl stapling on native peptides and proteins. NHS-activated acrylamides allow for a fast functionalization of N-terminal cysteines (k2=1.54±0.18×103 M?1 s?1) under dilute aqueous conditions, enabling selectivity over other nucleophilic amino acids. Additionally, the versatility of these new bioconjugation handles was demonstrated in the cross-linking of in-chain or C-terminal cysteines with nearby lysine residues. NHS-activated acrylamides are compatible with the use of other cysteine selective reagents, allowing for orthogonal dual-modifications. This strategy was successfully applied to the late-stage functionalization of peptides and proteins with a PEG unit, fluorescent probe, and cytotoxic agent. The level of molecular control offered by NHS-activated acrylamides is expected to promote amino-sulfhydryl stapling technology as a powerful strategy to design functional bioconjugates.
INDUCTION OF PHENYLPROPANOID PATHWAY ENZYMES IN ELICITOR-TREATED CULTURES OF CEPHALOCEREUS SENILIS
Pare, Paul W.,Mischke, Charles F.,Edwards, Robert,Dixon, Richard A.,Norman, Helen A.,Mabry, Tom J.
, p. 149 - 154 (1992)
Treatment of old-man-cactus (Cephalocereus senilis) suspension cultures with chitin elicits synthesis of an aurone phytoalexin, cephalocerone.Elicitor-induced de novo synthesis of cephalocerone was demonstrated by incubating elicited cactus cultures with phenylalanine; this resulted in the labelling of five induced phenolic compounds including cephalocerone.Increased extractable activities of the phenylpropanoid pathway enzymes phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS) and chalcone isomerase (CHI) accompanied the synthesis of cephalocerone.CHS and PAL, which are both involved in the biosynthesis of cephaloce rone, showed maximum activity at 12 and 24 hr post-elicitation, respectively.CHS and CHI activities catalysing the synthesis and subsequent isomerization of 2',4',6'-trihydroxychalcone were present in the cell cultures, consistent with the formation of cephalocerone via a chalcone with no B-ring substituents. Key Word Index - Cephalocereus senilis; Cactaceae; aurone; phytoalexin; enzyme induction; suspension culture; HPLC.
A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation
Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
supporting information, p. 807 - 811 (2018/02/06)
In this study, we performed a visible light-mediated aerobic photo-cross dehydrogenative coupling (CDC) reaction between aldehydes and N-hydroxyimides using TiO2-AA-Co as a photocatalyst for the synthesis of active esters. The synergistic and selective effects of the cobalt ascorbic acid complex (Co-AA) and TiO2 nanoparticles on the visible-light photocatalytic activity were explored. The method possesses some advantages such as environmentally friendly conditions, easy work-up procedure, reusability, and scalability.
Design, synthesis and structure-activity relationship studies of a novel focused library of 2,3,4-substituted oxazolidines with antiproliferative activity against cancer cell lines
Andrade, Saulo F.,Oliveira, Bárbara G.,Pereira, Larissa C.,Ramos, Jonas P.,Joaquim, Angélica R.,Steppe, Martin,Souza-Fagundes, Elaine M.,Alves, Ricardo J.
, p. 13 - 25 (2017/06/23)
In the present work we describe the synthesis and antiproliferative evaluation of a focused library of 30 novel oxazolidines designed by modification of N-substituent, by ring variation, by alkyl variation or by extension of the structure. It was noted that carbamate and N,O-aminal groups were essential for activity. In general, replacement of the phenyl ring with pyridinyl was not tolerated. However, the introduction of a second phenyl ring with an appropriate spacer at the 3- or 4-position of the first phenyl ring generally enhanced the cytotoxic profile. Among all the prepared compounds, 24 was the most potent compound found in this class, being active on four of five cancer cell lines and it was 5-fold and 10-fold more potent than the lead compounds against HL60 and JURKAT cells, respectively. In addition, it showed relevant activity against MCF-7 and HCT-116 cells, which were resistant to lead. Moreover, 24 showed little antiproliferative activity against VERO, indicating low toxicity to normal cells. Thus, this compound has the potential to be developed as an anticancer agent.
Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship
Fregnan, Antonio Maciel,Brancaglion, Guilherme Andrade,Galv?o, Alexandre Francisco Cerqueira,D’Sousa Costa, Cinara Oliveira,Moreira, Diogo Rodrigo Magalh?es,Soares, Milena Botelho Pereira,Bezerra, Daniel Pereira,Silva, Naiara Chaves,de Souza Morais, Stella Maria,Oliver, Josidel Concei??o,Dias, Amanda Latercia Tranches,Coelho, Luiz Felipe Leomil,Carvalho, Diogo Teixeira,Dias, Danielle Ferreira,de Souza, Thiago Belarmino
, p. 603 - 614 (2017/02/15)
In this work it is described the synthesis, characterization and antimicrobial and toxicity evaluation of a series of analogs of piplartine, a piperamide found in Piper sp. The compounds structures were confirmed by infrared spectroscopy, 1H, 13C nuclear magnetic resonance, high resolution mass spectroscopy and were evaluated against strains of Candida spp., Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Derivative 24 was almost four-fold more potent (IC50: 48.83 μM) and five-fold less toxic (SI > 3) than piplartine (IC50: 189.2 μM; SI: 0.21) against Candida krusei, as well as two-fold more potent than fluconazole (IC50: 104.48 μM). This compound was also active against Candida tropicalis at 97.67 μM. Benzoyl derivative 17 was three-fold more potent (IC50: 85.2 μM) and more than five-fold less toxic (CC50: 231.71 μM) than piplartine (IC50: 315.33 μM and CC50: 41.14 μM) against Staphylococcus aureus. Given these findings, we have found analogs of piplartine which can be assumed as prototypes for the optimization and the development of new antimicrobial (compounds 24 and 17) agents.
Method for synthesizing kukoamine A and analogue thereof
-
, (2017/01/02)
The invention relates to the technical field of medicines, and relates to a method for synthesizing a natural product kukoamine A and analogue thereof. The method comprises the following steps: (1) performing a nucleophilic reaction on hydroxyl, halogen or C1-C10 alkoxy or C1-C10 alkyl substituted or unsubstituted benzaldehyde and malonic acid to obtain a compound 1; (2) reacting the compound 1 in the step (1) with N-hydroxy succinimide to obtain a compound 2; (3) reacting the compound 2 with spermine to obtain a compound 3; and (4) reacting the compound 3 with hydrogen to reduce carbon-carbon double bond, and purifying. The preparation method is simple, and provides a compound base to pharmacological activity research of compounds with similar structures.
Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate
Barré, Ana?s,T?nta?, Mihaela-Liliana,Alix, Florent,Gembus, Vincent,Papamica?l, Cyril,Levacher, Vincent
, p. 6537 - 6544 (2015/10/05)
An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)2/Xantphos catalyst system.
One-pot synthesis of hydroxamic acids from aldehydes and hydroxylamine
Dettori, Giovanna,Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
supporting information, p. 2709 - 2713 (2014/09/17)
A one-pot oxidative transformation of aldehydes into hydroxamic acids by the use of an aqueous solution of hydroxylamine is reported. The methodology gives high yields and makes use of cheap, abundant and easily available reagents.
Iodide-catalyzed amide synthesis from alcohols and amines
Wang, Gao,Yu, Qing-Ying,Wang, Jian,Wang, Shan,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 21306 - 21310 (2013/11/06)
An efficient method to prepare amides by a cascade strategy was developed. Using nBu4NI or NaI as the catalyst and tert-butyl hydroperoxide as the oxidant, various alcohols reacted with N-hydroxysuccinimide or N-hydroxyphthalimide affording corresponding active esters in moderate to good yield. The resulting active esters were converted into amides smoothly in one pot. The Royal Society of Chemistry 2013.
A copper-catalysed amidation of aldehydes via N-hydroxysuccinimide ester formation
Pilo, Monica,Porcheddu, Andrea,De Luca, Lidia
, p. 8241 - 8246 (2013/12/04)
A copper-catalysed oxidative amidation of aldehydes via N-hydroxysuccinimide ester formation is reported. The methodology employed to prepare amides directly from aldehydes has a very wide scope, is high yielding, and does not need dry conditions. This cross-coupling reaction appears to be simple and makes use of cheap, abundant and easily available reagents.
