Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents.
The synthesis and antiallergic activity of a series of novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles are described. A number of the compounds inhibit the release of histamine from anti-IgE stimulated basophils obtained from allergic donors. Optimal inhibition is exhibited in benzothiophenes with a 3-alkoxy substituent in combination with a 5-methoxy, 6-methoxy, or a 5,6-dimethoxy group. Compound 13c (CI-959) also inhibited respiratory burst of human neutrophils and the release of mediators from anti-IgE-stimulated human chopped lung.
Connor
D T
DT
Department of Chemistry, Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, Michigan 48105.
Cetenko
W A
WA
Mullican
M D
MD
Sorenson
R J
RJ
Unangst
P C
PC
Weikert
R J
RJ
Adolphson
R L
RL
Kennedy
J A
JA
Thueson
D O
DO
Wright
C D
CD
D000888:Antibodies, Anti-Idiotypic / Q000276:immunology; D001491:Basophils / Q000187:drug effects / Q000276:immunology / Q000502:physiology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology; D004804:Eosinophils / Q000187:drug effects / Q000502:physiology; D006633:Histamine Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology; D006636:Histamine Release / Q000187:drug effects; D006801:Humans; D006967:Hypersensitivity / Q000097:blood; D007073:Immunoglobulin E / Q000276:immunology; D008168:Lung / Q000187:drug effects / Q000378:metabolism; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000502:physiology; D016897:Respiratory Burst / Q000187:drug effects; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000888:Antibodies, Anti-Idiotypic; D001572:Benzofurans; D006633:Histamine Antagonists; D009281:Naphthalenes; D013777:Tetrazoles; D013876:Thiophenes; C061662:CI 959; D007073:Immunoglobulin E