Biomaterial Database

Antifilarial agents. 1,2-Cyclobutanediamines as analogues of diethylcarbamazine. Status of structure-activity relationships among diethylcarbamazine analogues. 1977

J W McCall, and J B Ziegler

cis-and trans-1,2-cyclobutanediamines bearing appropriate N-methyl and N-acyl substituents were prepared as analogues of diethylcarbamazine (DEC). None displayed activity against Litomosoides carinii in the gerbil despite substantial structural and sterochemical similarities to the parent drug. The inactivity of these drugs is rationalized in terms of eclipsed pharmacophore configurations and the increased population of unfavorable rotational conformations made possible by the exocyclic position of both pharmacophores. To provide perspective for these conclusions, the literature on DEC analogues is briefly summarized and structure-activity data are discussed in terms of critical structural factors associated with microfilaricidal activity. Generalizations on structural principles governing activity are advanced which encompass test results for the large majority of DEC analogues.

UI	MeSH Term	Description	Entries
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D003959	Diamines	Organic chemicals which have two amino groups in an aliphatic chain.	Diamine
D004049	Diethylcarbamazine	An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.	Carbamazine,Diethylcarbamazine Citrate,Diethylcarbamazine Citrate (1:1),Diethylcarbamazine Citrate (1:2),Diethylcarbamazine L-Tartrate (1:1),Diethylcarbamazine Maleate,Diethylcarbamazine Monohydrochloride,Diethylcarbamazine Phosphate (1:1),Hetrazan,Loxuran,Notezine,Citrate, Diethylcarbamazine,Maleate, Diethylcarbamazine,Monohydrochloride, Diethylcarbamazine
D005369	Filaricides	Pharmacological agents destructive to nematodes in the superfamily Filarioidea.
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
D000871	Anthelmintics	Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.	Anthelmintic,Antihelmintic,Vermifuge,Vermifuges,Antihelmintics
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