Use of the Adamantane Structure in Medicinal Chemistry

Abstract

This review summarizes the importance and recent discoveries of the use of adamantane derivatives in Medicinal Chemistry. We have organized the article in 4 sections: 1) Absorption, Distribution, Metabolism, or Excretion (ADME) properties 2) Hydrophobic Effects 3) Ion Channels and 4) Rigid scaffold. Within each section, we have provided examples of how the adamantane group changes the properties of known drugs or provides a important pharmacophore for the design of new drugs.

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S

“…Isothiourea derivatives were also reported to display potent antimicrobial [7,8], anticancer [9,10], and anti-anthelmintic [11] activities. The incorporation of the highly lipophilic adamantyl group positively modulates the therapeutic index of several compounds through various mechanisms [12,13]. Various adamantane derivatives are known for their antiviral activity against the influenza A [ [14][15][16], human immunodeficiency (HIV) [17][18][19] and herpes simplex [20] viruses.…”

Crystal structure of 4-bromobenzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C28H34BrN3S

“…The incorporation of an adamantyl group positively modulates the therapeutic index of several compounds through various mechanisms [1,2]. Several adamantane derivatives have long been known for their antiviral activity against the in uenza A [3][4][5][6], human immunode ciency (HIV) [7][8][9] and herpes simplex [10] viruses.…”

Crystal structure of 1-(adamantan-1-yl)-3-phenylthiourea, C17H22N2S

“…The adamantane nucleus represent an important structural motif in several biologically and pharmaceutically active drugs [1,2]. Several adamantane-based drugs are currently used as e cient medications against in uenza viral …”