219938-18-8Relevant academic research and scientific papers
Synthesis, immunosuppressive properties, and mechanism of action of a new isoxazole derivative
Maczynski, Marcin,Borska, Sylwia,Miesza?a, Katarzyna,Kocieba, Maja,Zaczynska, Ewa,Kochanowska, Iwona,Zimecki, Micha?
, (2018/07/13)
This work describes the synthesis of a new series of isoxazole derivatives, their immunosuppressive properties, and the mechanism of action of a representative compound. A new series of N-substituted derivatives of 5-amino-N,3- dimethyl-1,2-oxazole-4-carbohydrazide (MM1–MM10) was synthesized in reaction of 5-amino- N,3-dimethyl-1,2- oxazole-4- carbohydrazide with relevant carbonyl compounds. The isoxazole derivatives were tested in several in vitro models using human cells. The compounds inhibited phytohemagglutinin A (PHA)-induced proliferation of peripheral blood mononuclear cells (PBMCs) to various degrees. The toxicity of the compounds with regard to a reference A549 cell line was also differential. 5-amino-N-(2,4-dihydroxyphenyl) methylidene-N,3-dimethyl-1,2-oxazole-4-carbohydrazide (MM3) compound was selected for further investigation because of its lack of toxicity and because it had the strongest antiproliferative activity. The compound was shown to inhibit lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF α) production in human whole blood cell cultures. In the model of Jurkat cells, MM3 elicited strong increases in the expression of caspases, Fas, and NF-κB1, indicating that a proapoptotic action may account for its immunosuppressive action in the studied models.
Search for new lead structures for low-molecular-weight immune response modifiers.
Ryng, Stanislaw,Zimecki, Michal
, p. 78 - 81 (2007/10/03)
In this report we describe different types of 5-amino-3-methylisoxazolo-4-carboxylic acid amides and 5-amino-3-methylisoxazolo-4-ureilenes and their immunological activities. The immunoregulatory activities were tested in the humoral and cellular immune response in mice. The compounds exhibited both immunostimulatory and immunosuppressory activities.
Synthesis and X-ray structure of New 5-amino-methyl-4-isoxazolecarboxylic acid azides
Ryng, Stanislaw,Machon, Zdzislaw,Glowiak, Tadeusz
, p. 483 - 488 (2007/10/02)
The syntheses of the new heterocyclic azides which open a number ways of obtaining interesting isoxazole derivatives has been described.Chemical, spectral and X-ray data giving the evidence of the structure of these compounds are presented.X-ray studies were carried out on compounds I,II(C5H5N5O2, C12H9N5O3) with a = 3.775(2), 7.179(3); b = 11.593(3), 8.135(3); c = 8.443(3), 11.610(3); Z = 2,2 and space group Pn, P1.The structure was established using direct methods and refined by weighted full-matrix least squares.The refinement, based on 687 reflections for I, and 1648 for II with I>/? 3.0 (I), converged to a final R of 0.333, 0.034 and Rw = 0.036, 0.032.KEY WORDS: Heterocyclic azides, isoxazoles, heteroaromatic compounds.
