7625-53-8Relevant articles and documents
N-Pyrazinoyl substituted amino acids as potential antimycobacterial agents-the synthesis and biological evaluation of enantiomers
Bárta, Pavel,Dole?al, Martin,Horá?ek, Ond?ej,Jand'Ourek, Ond?ej,Janou?ek, Ji?í,Juhás, Martin,Kone?ná, Klára,Ku?era, Radim,Ku?erová, Lucie,Kubí?ek, Vladimír,Kune?, Ji?í,Paterová, Pavla,Zitko, Jan
, (2020/04/09)
Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 μM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC 1.95 μg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds.
Synthesis, insecticidal activities and SAR studies of novel anthranilic diamides containing trifluoroethoxyl substituent and chiral amino acid moieties
Zhou, Shaa,Zhou, Sha,Xie, Yongtao,Meng, Xiangde,Wang, Baolei,Xiong, Lixia,Yang, Na,Li, Zhengming
supporting information, p. 1254 - 1256 (2017/11/24)
Ryanodine receptors (RyRs) activator has become one class of popular insecticide because of its unique mode of action. In order to find more new RyRs activators as insecticidal agents, a series of 18 novel chiral anthranilic diamides were designed by introducing the D-alanine acid and D-serine acid esters as well as trifluoroethoxyl group into the anthranilic diamide skeleton and synthesized successfully based on anthranilic diamide and FKI-1033 structures. The structures of the title compounds Ia–i and IIa–i were confirmed by melting points, 1H NMR, 13C NMR, elemental analysis and specific optical rotation analysis. The preliminary bioassay results indicated that most of the title compounds exhibited considerable larvicidal activities against oriental armyworm at 10 mg/L, especially Ib, Ie and IIh showed remarkable insecticidal activities at 0.5 mg/L. The larvicidal activity against diamondback moth of Ia and IId were 80% and 90% respectively at 0.0001 mg/L, which was similar to that of chlorantraniliprole. The relationship between structure and insecticidal activity was analyzed to reveal a possible co-regulated effect of the chiral amino acid ester, halogen atom or cyano group, and trifluoroethyloxyl group of the skeleton structures of the title compounds, which will provide useful information for guiding the design and discovery of new RyRs activators and insecticidal agrochemicals.
Chiral phosphorescent probes for amino acids: hybrids of iridium(iii) complexes with synthetic saponite
Sato, Hisako,Tamura, Kenji,Yajima, Tomoko,Sato, Fumi,Yamagishi, Akihiko
, p. 2780 - 2785 (2017/04/03)
An attempt of developing a chiral luminescent probe for amino acids was described. Two types of chiral iridium(iii) complexes were synthesized: [Ir(dfppy)2(R-pep-bpy)]+ (dfppyH = 2-(2′,4′-difluorophenyl)pyridine); R-pep-bpy = 4,4′-bis((R-1,2-dimethylpropyl)aminocarbonyl-2,2′-bipyridine) and [Ir(piq)2(R-pep-bpy)]+ (piqH = 1-phenyisoquinoline). In both complexes, amido groups (R-pep-) were attached to 2,2′-bipyridine with an intension of increasing the affinity for an amino acid. The complexes were optically resolved on a chiral column. When the complexes were adsorbed by the colloidal particles of synthetic saponite, they were highly emissive even in a medium containing water. The remarkable quenching of emission was observed for the combination of [Ir(dfppy)2(R-pep-bpy)]+ and tryptophan methyl ester. By the use of the enantiomeric complexes, the possibility of enantioselective quenching was examined for various amino acid derivatives.
