1.
J Med Chem
; 21(11): 1120-6, 1978 Nov.
Article
in English
| MEDLINE
| ID: mdl-82617
ABSTRACT
A series of chromones containing an acidic group has been synthesized and screened for the ability to inhibit passive cutaneous anaphylaxis and the release of histamine from mast cells of the rat. Many of the chromones contain the N-(5-tetrazolyl)carboxamido group, a novel source of acidity. Others contain a carboxyl, C-(5-tetrazolyl), 5-(4H)-oxotetrazolinyl, or N-(5-tetrazolyl)sulfonamido function. The compounds were compared with cromolyn sodium (sodium cromoglycate) and many were found to be powerful inhibitors of anaphylaxis. The most potent was 7-methoxy-4-oxo-N-(5-tetrazolyl)-4H-1-benzopyran-2-carboxamide (15). Structure-activity relationships among the chromones and also some related compounds are discussed.
Subject(s)
Azoles/chemical synthesis , Chromones/chemical synthesis , Hypersensitivity/drug therapy , Tetrazoles/chemical synthesis , Anaphylaxis/metabolism , Animals , Chromones/pharmacology , Female , Histamine Release/drug effects , Humans , In Vitro Techniques , Lung/drug effects , Lung/metabolism , Male , Mast Cells/drug effects , Mast Cells/metabolism , Passive Cutaneous Anaphylaxis/drug effects , Rats , Structure-Activity Relationship , Tetrazoles/pharmacology
2.
Prog Med Chem
; 10: 245-85, 1974.
Article
in English
| MEDLINE
| ID: mdl-4617902
Subject(s)
Nitriles/chemical synthesis , Aluminum , Amides , Cyanides , Lithium , Methods , Organometallic Compounds , Structure-Activity Relationship
3.
J Med Chem
; 16(1): 87-9, 1973 Jan.
Article
in English
| MEDLINE
| ID: mdl-4404823
4.
J Med Chem
; 15(8): 865-7, 1972 Aug.
Article
in English
| MEDLINE
| ID: mdl-5044310
Subject(s)
Benzopyrans/chemical synthesis , Hypersensitivity/drug therapy , Animals , Azoles/chemical synthesis , Azoles/therapeutic use , Azoles/toxicity , Benzopyrans/therapeutic use , Benzopyrans/toxicity , Ketones/chemical synthesis , Ketones/therapeutic use , Ketones/toxicity , Lethal Dose 50 , Mice , Passive Cutaneous Anaphylaxis , Rats , Structure-Activity Relationship
5.
Prog Med Chem
; 9(1): 65-116, 1972.
Article
in English
| MEDLINE
| ID: mdl-4564214
Subject(s)
Carboxylic Acids , Chromones , Acylation , Animals , Benzene , Bronchodilator Agents , Carboxylic Acids/chemical synthesis , Chromones/chemical synthesis , Color , Crystallization , Esters/chemical synthesis , Humans , Hydrogen-Ion Concentration , Hypersensitivity/drug therapy , Macromolecular Substances , Magnetic Resonance Spectroscopy , Models, Chemical , Pyrans , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Spectrum Analysis , Temperature , Vasodilator Agents
6.
Prog Med Chem
; 6: 266-368, 1969.
Article
in English
| MEDLINE
| ID: mdl-4894875
Subject(s)
Bibliographies as Topic , Chemistry, Pharmaceutical , Pharmacology , Alkaloids , Carbohydrates , Chromatography , Hormones , Lipids , Nucleic Acids , Pharmaceutical Preparations , Proteins , Radiochemistry , Spectrum Analysis , Steroids , Vitamins
7.
J Med Chem
; 10(1): 130-1, 1967 Jan.
Article
in English
| MEDLINE
| ID: mdl-6031697
