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Structure-activity relationship at alpha-adrenergic receptors within a series of imidazoline analogues of cirazoline. 2000

M Pigini, and W Quaglia, and F Gentili, and G Marucci, and F Cantalamessa, and S Franchini, and C Sorbi, and L Brasili
Dipartimento di Scienze Chimiche, Università degli Studi di Camerino, Italy.

Several analogues of cirazoline (2), a selective alpha1-adrenoreceptor agonist, were prepared and their pharmacological profiles studied. Although at the alpha1-adrenoreceptor all the compounds displayed a significant agonist activity, at the alpha2-adrenoreceptor they showed either agonist or antagonist activity depending on the nature of the phenyl substituent. The qualitative structure-activity relationship led us to the conclusion that the oxygen atom in the side-chain is essential for alpha1-agonist activity, while the cyclopropyl ring is not, and may be replaced by several groups. Of the groups studied, isopropoxy appears to be the best. Instead, the same substitution (i.e., isopropoxy for the cyclopropyl ring) at alpha2-adrenoreceptors causes a reversal of activity. On the other hand, the cyclopropyl ring seems to be important for alpha1-selectivity. Compound 20 is the most potent alpha1-agonist of the series, being equiactive with cirazoline on rat vas deferens and in pithed rat.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D008297 Male Males
D001794 Blood Pressure PRESSURE of the BLOOD on the ARTERIES and other BLOOD VESSELS. Systolic Pressure,Diastolic Pressure,Pulse Pressure,Pressure, Blood,Pressure, Diastolic,Pressure, Pulse,Pressure, Systolic,Pressures, Systolic
D000316 Adrenergic alpha-Agonists Drugs that selectively bind to and activate alpha adrenergic receptors. Adrenergic alpha-Receptor Agonists,alpha-Adrenergic Receptor Agonists,Adrenergic alpha-Agonist,Adrenergic alpha-Receptor Agonist,Receptor Agonists, Adrenergic alpha,Receptor Agonists, alpha-Adrenergic,alpha-Adrenergic Agonist,alpha-Adrenergic Agonists,alpha-Adrenergic Receptor Agonist,Adrenergic alpha Agonist,Adrenergic alpha Agonists,Adrenergic alpha Receptor Agonist,Adrenergic alpha Receptor Agonists,Agonist, Adrenergic alpha-Receptor,Agonist, alpha-Adrenergic,Agonist, alpha-Adrenergic Receptor,Agonists, Adrenergic alpha-Receptor,Agonists, alpha-Adrenergic,Agonists, alpha-Adrenergic Receptor,Receptor Agonist, alpha-Adrenergic,Receptor Agonists, alpha Adrenergic,alpha Adrenergic Agonist,alpha Adrenergic Agonists,alpha Adrenergic Receptor Agonist,alpha Adrenergic Receptor Agonists,alpha-Agonist, Adrenergic,alpha-Agonists, Adrenergic,alpha-Receptor Agonist, Adrenergic,alpha-Receptor Agonists, Adrenergic
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
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
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
D018340 Receptors, Adrenergic, alpha-1 A subclass of alpha-adrenergic receptors that mediate contraction of SMOOTH MUSCLE in a variety of tissues such as ARTERIOLES; VEINS; and the UTERUS. They are usually found on postsynaptic membranes and signal through GQ-G11 G-PROTEINS. Adrenergic alpha-1 Receptors,Receptors, alpha-1 Adrenergic,alpha-1 Adrenergic Receptors,Adrenergic Receptor, alpha-1,Adrenergic alpha-1A Receptors,Adrenergic alpha-1B Receptors,Adrenergic alpha-1D Receptors,Receptor, Adrenergic, alpha-1,Receptor, Adrenergic, alpha-1A,Receptor, Adrenergic, alpha-1B,Receptor, Adrenergic, alpha-1D,Receptors, Adrenergic, alpha-1A,Receptors, Adrenergic, alpha-1B,Receptors, Adrenergic, alpha-1D,alpha 1 Adrenergic Receptor,alpha-1A Adrenergic Receptor,alpha-1B Adrenergic Receptor,alpha-1C Adrenergic Receptor,alpha-1D Adrenergic Receptor,Adrenergic Receptor, alpha 1,Adrenergic Receptor, alpha-1A,Adrenergic Receptor, alpha-1B,Adrenergic Receptor, alpha-1C,Adrenergic Receptor, alpha-1D,Adrenergic Receptors, alpha-1,Adrenergic alpha 1 Receptors,Adrenergic alpha 1A Receptors,Adrenergic alpha 1B Receptors,Adrenergic alpha 1D Receptors,Receptor, alpha-1 Adrenergic,Receptor, alpha-1A Adrenergic,Receptor, alpha-1B Adrenergic,Receptor, alpha-1C Adrenergic,Receptor, alpha-1D Adrenergic,Receptors, Adrenergic alpha-1,Receptors, Adrenergic alpha-1A,Receptors, Adrenergic alpha-1B,Receptors, Adrenergic alpha-1D,Receptors, alpha 1 Adrenergic,alpha 1 Adrenergic Receptors,alpha 1A Adrenergic Receptor,alpha 1B Adrenergic Receptor,alpha 1C Adrenergic Receptor,alpha 1D Adrenergic Receptor,alpha-1 Adrenergic Receptor,alpha-1 Receptors, Adrenergic,alpha-1A Receptors, Adrenergic,alpha-1B Receptors, Adrenergic,alpha-1D Receptors, Adrenergic

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