BIOMAT Database Logo BIOMAT Database Logo

Studies on antiallergic agents. II. Quantitative structure-activity relationships of novel 6-substituted N-(1H-tetrazol-5-yl)-2-pyrazinecarboxamides. 1990

E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Central Research Laboratories, Hokuriku Seiyaku Co., Ltd., Fukui, Japan.

The effect of structural modifications of 6-substituted N-(1H-tetrazol-5-yl)-2-pyrazinecarboxamides on their anti-allergic activity was analyzed quantitatively by means of the Hansch-Fujita method. The activity of these compounds was correlated with hydrophobic (pi) and steric (molecular refractivity and STERIMOL B1) effects of the 6-substituent on the pyrazine ring. The 6-substituents with a length greater than n-propylamino possess an extra effect enhancing the activity. Moreover, the activity increased progressively from 6-non-amino via alkylamino- to dialkylamino-substituted compounds, other factors being equal. This could be attributable to an electronic effect of substituents. Electron-donating small and yet symmetric substituents with high hydrophobicity longer than n-propylamino seemed to be favorable to the activity. By compromising these contradictory requirements, small dialkylamino (including cyclic amino) groups were decided to be the most favorable substituents. This analysis was in agreement with the observation that the most effective compounds were the 6-dimethylamino (I-27) and 6-(1-pyrrolidinyl) (I-34) derivatives.

UI MeSH Term Description Entries
D006967 Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen. Allergy,Allergic Reaction,Allergic Reactions,Allergies,Hypersensitivities,Reaction, Allergic,Reactions, Allergic
D011719 Pyrazines A heterocyclic aromatic organic compound with the chemical formula C4H4N2. Pyrazine
D011759 Pyrrolidines Compounds also known as tetrahydropyridines with general molecular formula (CH2)4NH. Tetrahydropyridine,Tetrahydropyridines
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.
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
D001393 Azoles Five membered rings containing a NITROGEN atom. Azole
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
D013777 Tetrazoles
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus
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

E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Antiallergic agents. 2. N-(1H-tetrazol-5-yl)-6-phenyl-2-pyridinecarboxamides.
October 1983, Journal of medicinal chemistry,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Antiallergic agents. 3. N-(1H-tetrazol-5-yl)-2-pyridinecarboxamides.
February 1984, Journal of medicinal chemistry,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides.
April 1986, Journal of medicinal chemistry,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Studies on antianaphylactic agents. 5. Synthesis of 3-(1H-tetrazol-5-yl)chromones, a new series of antiallergic substances.
January 1977, Journal of medicinal chemistry,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Antiallergy agents. 2. 2-Phenyl-5-(1H-tetrazol-5-yl)pyrimidin-4(3H)-ones.
October 1982, Journal of medicinal chemistry,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Quantitative structure-activity relationship study on N-(pyridin-4-yl)-(indol-3-yl) alkylamides as antiallergic agents.
October 2002, Indian journal of biochemistry & biophysics,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Antiallergic action of 6-ethyl-3-(1h-tetrazol-5-YL) chromone (AA-344) on immediate hypersensitivity reaction in rats.
June 1979, Japanese journal of pharmacology,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Synthesis and potent antimicrobial activity of some novel 4-(5, 6-dichloro-1H-benzimidazol-2-yl)-N-substituted benzamides.
October 2004, Archiv der Pharmazie,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Studies on antianaphylactic agents. 6. Synthesis of some metabolites of 6-ethyl-3-(1H-tetrazol-5-yl)chromone and their analogues.
March 1979, Journal of medicinal chemistry,
E Makino, and K Mitani, and N Iwasaki, and H Kato, and Y Ito, and H Azuma, and T Fujita
Quantitative structure-activity relationships in a series of antiallergic agents.
January 1982, Arzneimittel-Forschung,
Copied contents to your clipboard!