title: Synthesis and biological evaluation of new 1,3-thiazolidine-4-one derivatives of nitro-l-arginine methyl ester.
abstract: BACKGROUND
  l-Arginine is a semi-essential aminoacid with important role in regulation of physiological processes in humans. It serves as precursor for the synthesis of proteins and is also substrate for different enzymes such as nitric oxide synthase. This amino-acid act as free radical scavenger, inhibits the activity of pro-oxidant enzymes and thus acts as an antioxidant and has also bactericidal effect against a broad spectrum of bacteria.
  
  
  RESULTS
  New thiazolidine-4-one derivatives of nitro-l-arginine methyl ester (NO2-Arg-OMe) have been synthesized and biologically evaluated in terms of antioxidant and antibacterial/antifungal activity. The structures of the synthesized compounds were confirmed by (1)H, (13)C NMR, Mass and IR spectral data. The antioxidant potential was investigated using in vitro methods based on ferric/phosphomolybdenum reducing antioxidant power and DPPH/ABTS radical scavenging assay. The antibacterial effect was investigated against Gram positive (Staphylococcus aureus ATCC 25923, Sarcina lutea ATCC 9341) and Gram negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) bacterial strains. The antifungal activity was also investigated against Candida spp. (Candida albicans ATCC 10231, Candida glabrata ATCC MYA 2950, Candida parapsilosis ATCC 22019).
  
  
  CONCLUSIONS
  Synthesized compounds showed a good antioxidant activity in comparison with the NO2-Arg-OMe. The antimicrobial results support the selectivity of tested compounds especially on P. aeruginosa as bacterial strain and C. parapsilosis as fungal strain. The most proper compounds were 6g (R = 3-OCH3) and 6h (R = 2-OCH3) which showed a high free radical (DPPH, ABTS) scavenging ability and 6j (R = 2-NO2) that was the most active on both bacterial and fungal strains and also it showed the highest ABTS radical scavenging ability.Graphical abstract1: ethyl 3-aminopropionate hydrochloride, 2a-j: aromatic aldehydes, 3: thioglycolic acid, 4a-j: thiazolidine-propionic acid derivatives , 5: Nω-nitro-L-arginine methyl ester hydrochloride, 6a-j: thiazolidine-propionyl-nitro-L-arginine methyl ester derivatives.
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Andreea-Teodora
authors: AT
authors: Pânzariu
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Maria
authors: M
authors: Apotrosoaei
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Ioana Mirela
authors: IM
authors: Vasincu
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Maria
authors: M
authors: Drăgan
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Sandra
authors: S
authors: Constantin
authors: Institut de Chimie Organique et Analytique - ICOA UMR7311, Pôle de chimie, Rue de Chartres, 45100 Orléans, France.
authors: Frédéric
authors: F
authors: Buron
authors: Institut de Chimie Organique et Analytique - ICOA UMR7311, Pôle de chimie, Rue de Chartres, 45100 Orléans, France.
authors: Sylvain
authors: S
authors: Routier
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Lenuta
authors: L
authors: Profire
authors: Department of Microbiology, Faculty of Pharmacy, University of Medicine and Pharmacy "Grigore T. Popa", 16 University Street, 700115 Iasi, Romania.
authors: Cristina
authors: C
authors: Tuchilus
keywords: 1,3-Thiazolidine-4-one; Antibacterial/antifungal activity; Antioxidant effects; Nitro-l-arginine methyl ester; Spectral methods