BIOMAT Database Logo BIOMAT Database Logo

Preparation of triazolo[1,5-c]pyrimidines as potential antiasthma agents. 1990

J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Medical Research Division, American Cyanamid Company, Lederle Laboratories, Pearl River, New York 10965.

With the use of the human basophil histamine release assay, 5-aryl-2-amino[1,2,4]triazolo[1,5-c]pyrimidines were found to be active as mediator release inhibitors. These compounds were prepared by reacting arylamidines with sodium ethyl formylacetate or with ethyl propiolate to give pyrimidinones. Treatment with phosphorus oxychloride gave a chloropyrimidine, which was converted to a hydrazinopyrimidine with hydrazine. Cyclization, using cyanogen bromide, gave the triazolo[1,5-c]pyrimidines, after a Dimroth rearrangement. Following a structure-activity evaluation, the 5-[3-(trifluoromethyl)phenyl]-2-amino (8-10), 5-(3-bromophenyl)-2-amino (8-13), 5-[3-(difluoromethoxy)-phenyl]-2-amino (8-11), and 5-(4-pyridinyl)-2-amino (6-7) compounds were found to have the best activity. They were chosen for further pharmacological and toxicological study.

UI MeSH Term Description Entries
D010323 Passive Cutaneous Anaphylaxis An evanescent cutaneous reaction occurring when antibody is injected into a local area on the skin and antigen is subsequently injected intravenously along with a dye. The dye makes the rapidly occurring capillary dilatation and increased vascular permeability readily visible by leakage into the reaction site. PCA is a sensitive reaction for detecting very small quantities of antibodies and is also a method for studying the mechanisms of immediate hypersensitivity. Anaphylaxis, Passive Cutaneous,PCA,Cutaneous Anaphylaxis, Passive
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.
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D005260 Female Females
D006634 Histamine H1 Antagonists Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. Antihistamines, Classical,Antihistaminics, Classical,Antihistaminics, H1,Histamine H1 Antagonist,Histamine H1 Receptor Antagonist,Histamine H1 Receptor Antagonists,Histamine H1 Receptor Blockaders,Antagonists, Histamine H1,Antagonists, Histamine H1 Receptor,Antihistamines, Sedating,Blockaders, Histamine H1 Receptor,First Generation H1 Antagonists,H1 Receptor Blockaders,Histamine H1 Blockers,Receptor Blockaders, H1,Antagonist, Histamine H1,Classical Antihistamines,Classical Antihistaminics,H1 Antagonist, Histamine,H1 Antagonists, Histamine,H1 Antihistaminics,Sedating Antihistamines
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
D001249 Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL). Asthma, Bronchial,Bronchial Asthma,Asthmas
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

Related Publications

J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Discovery of [1,2,4]triazolo[1,5-a]pyrimidines derivatives as potential anticancer agents.
February 2021, European journal of medicinal chemistry,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Imidazo[1,5-d][1,2,4]triazines as potential antiasthma agents.
November 1985, Journal of medicinal chemistry,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Synthesis of certain new 2,4,5(6) trisubstituted-1,2,4-triazolo[1,5-alpha]pyrimidines as potential antihypertensive agents.
May 1999, Bollettino chimico farmaceutico,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Synthesis and evaluation of 1,2,4-triazolo[1,5-a]pyrimidines as antibacterial agents against Enterococcus faecium.
May 2015, Journal of medicinal chemistry,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Pyrrolo- and pyrazolo-[3,4-e][1,2,4]triazolo[1,5-c]pyrimidines as adenosine receptor antagonists.
January 2012, Bioorganic & medicinal chemistry,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
2-(Alkylthio)-1,2,4-triazolo[1,5-a]pyrimidines as adenosine cyclic 3',5'-monophosphate phosphodiesterase inhibitors with potential as new cardiovascular agents.
April 1982, Journal of medicinal chemistry,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
[Synthesis of new s-triazolo (1,5-a)pyrimidines].
January 1978, Die Pharmazie,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines.
February 2009, Bioorganic & medicinal chemistry letters,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
Synthesis and evaluation of ursolic acid-based 1,2,4-triazolo[1,5-a]pyrimidines derivatives as anti-inflammatory agents.
February 2022, Molecular diversity,
J B Medwid, and R Paul, and J S Baker, and J A Brockman, and M T Du, and W A Hallett, and J W Hanifin, and R A Hardy, and M E Tarrant, and L W Torley
1,2,4-Triazolo[1,5-a]pyrimidines in drug design.
March 2019, European journal of medicinal chemistry,
Copied contents to your clipboard!