BIOMAT Database Logo BIOMAT Database Logo

Synthesis and pharmacological screening of derivatives of isoxazolo[4,5-d]pyrimidine. 2008

Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Department of Drugs Technology, Wroclaw Medical University, Pl. Nankiera 1, 50-140 Wroclaw, Poland. wagner@ktl.am.wroc.pl

A number of derivatives of isoxazolo[4,5-d]pyrimidine were prepared with structures similar to that of purine. Condensation of the hydrazide of 4-amino-5-benzoylisoxazolo-3-carboxylic acid 2 with ethyloxalyl chloride followed by cyclization gave 3-oxdiazolo-[1,3,4]-4-amino-5-benzoylisoxazole 7 which, upon cyclization with acetonitrile followed by reactions with different amines, gave derivatives of isoxazolo[4,5-d]pyrimidine 9 and 10d-g. Compounds 8g and 10f were tested for their effects on the immune response in the mouse model. Both compounds significantly inhibited the humoral immune response in vivo to sheep erythrocytes at a dose of 100 microg, whereas in the delayed type hypersensitivity assay a suppressive activity was shown only by compound 10f. In addition, compound 8g inhibited and compound 10f stimulated the proliferative response of mouse splenocytes to concanavalin A. The results indicated that compound 10f was a universal inhibitor of the immune response, while compound 8g selectively suppressed the humoral immune response.

UI MeSH Term Description Entries
D007555 Isoxazoles Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions. Isoxazole
D008297 Male Males
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D004353 Drug Evaluation, Preclinical Preclinical testing of drugs in experimental animals or in vitro for their biological and toxic effects and potential clinical applications. Drug Screening,Evaluation Studies, Drug, Pre-Clinical,Drug Evaluation Studies, Preclinical,Drug Evaluations, Preclinical,Evaluation Studies, Drug, Preclinical,Evaluation, Preclinical Drug,Evaluations, Preclinical Drug,Medicinal Plants Testing, Preclinical,Preclinical Drug Evaluation,Preclinical Drug Evaluations,Drug Screenings,Screening, Drug,Screenings, Drug
D005260 Female Females
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013154 Spleen An encapsulated lymphatic organ through which venous blood filters.
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

Related Publications

Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis and pharmacological assessment of derivatives of isoxazolo[4,5-d]pyrimidine.
January 2004, Bioorganic & medicinal chemistry,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis and pharmacological properties of derivatives of isoxazolo[4,3-d]pyrimidine. III.
March 1995, Farmaco (Societa chimica italiana : 1989),
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis and preliminary pharmacological assessment of derivatives of isoxazolo[4,3-d]pyrimidine. II.
January 1994, Acta poloniae pharmaceutica,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis and pharmacological screening of derivatives of isoxazolo[4, 3-d]pyridimidine.I.
January 1994, Farmaco (Societa chimica italiana : 1989),
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
[Synthesis and biological properties of isoxazolo[5,4-d]pyrimidine derivatives].
January 1984, Acta poloniae pharmaceutica,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis of derivatives of thiazolo[4,5-d]pyrimidine. II.
January 1970, Journal of the Chemical Society. Perkin transactions 1,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis and pharmacological properties of derivatives of isoxazolo [5,4-d]-6,7-dihydropyrimidines.
January 1988, Polish journal of pharmacology and pharmacy,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Synthesis of thiazolo[4,5-d]pyrimidine derivatives as potential antimicrobial agents.
December 2007, Archives of pharmacal research,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
Design, Synthesis and Cytotoxic Evaluation of N-Acylhydrazone-Incorporated Isoxazolo[4,5-d]pyridazin-4(5H)-one Derivatives.
September 2022, Chemistry & biodiversity,
Edwin Wagner, and Kamal Al-Kadasi, and Michał Zimecki, and Wanda Sawka-Dobrowolska
SYNTHESIS, ANTI-HEPATITIS B AND C VIRUS ACTIVITY AND ANTITUMOR SCREENING OF NOVEL THIAZOLO[4,5-D]-PYRIMIDINE DERIVATIVES.
January 2016, Acta poloniae pharmaceutica,
Copied contents to your clipboard!