Imidazoline scaffold in medicinal chemistry: a patent review (2012–2015)

ABSTRACT

Introduction: Until very recently, the ‘imidazoline drugs’ were perceived as a class of central and/or peripheral sympatholytics and vasodilators acting at either the imidazoline binding sites and/or α-adrenergic receptors. However, in recent years it has become evident that the imidazoline scaffold is also contained in synthetic agents that exhibit a broad spectrum of biological activities.

Areas covered: This review provides an insight into the patents filed in the years 2012–2015, and considers 2-imidazoline-containing compounds with proven biological properties. Special attention is paid to agents for which practical applications as active ingredients of pharmaceutical compositions, diagnostic imaging agents, insecticides and herbicides, may be found.

Expert opinion: 2-Substituted imidazolines can exist in multiple tautomeric forms. The implication is that imidazolines and their imidazolidine tautomers cannot be regarded as isofunctional structures and the term ‘imidazoline scaffold’ should be treated with caution. Nevertheless, for medicinal chemists the progress made in development of both the imidazoline- and imidazolidine-containing agents useful for the treatment of neurodegenerative, inflammatory, autoimmune, cancer, and infectious diseases is of the utmost importance.

KEYWORDS:

• Biological activities
• imidazolines
• imidazolidines
• structure
• therapeutic applications

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Corrigendum

Article highlights

• Imidazoline scaffold, a small five-membered diaza heterocyclic ring is thoroughly explored in the design and development of new drugs.

• 2-imidazoline and 2-aminoimidazoline moieties may serve as bioisosteric groups of amidine and guanidine functionalities, respectively.

• During the period between 2012–2015 a great number of potential drugs with either the imidazoline scaffold have been discovered, useful for the treatment of neurodegenerative, inflammatory, autoimmune, cancer and infectious diseases.

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Declaration of interest

The authors have no relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.

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Funding

This paper was not funded.