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Current and Future Applications of Diamondoids and Their Derivatives
Published in Sven Stauss, Kazuo Terashima, Diamondoids, 2017
Rimantadine (alpha-methyl-1-adamantane-methylamine hydrochloride) is another adamantane derivative, in addition to amantadine and memantine (see Fig. 4.4). Amantadine (1-adamantanemine hydrochloride) and memantine (displayed in the middle of Fig. 4.4) both show anti-Parkinsonian activity. In the following paragraphs, we treat the case of rimantadine. In 1993, rimantadine, which is the alpha-methyl derivative of amantadine, was approved by the US Food and Drug Administration for the prophylaxis and treatment of influenza A virus (although later studies suggest that the activity against influenza A decreased). Compared to amantadine, rimantadine has a few advantageous properties: It has fewer central nervous and sleep side effects.Its elimination half-life, that is, the time it takes the body to reduce its quantity by half, is about 24 to 36 hours, compared to 12–18 hours for amantadine.It possesses a 10 times higher partition coefficient when compared to amantadine.
Synthesis of novel adamantane-containing dihydropyrimidines utilizing Biginelli condensation reaction
Published in Journal of Sulfur Chemistry, 2023
Mina Abkar Aras, Adeleh Moshtaghi Zonouz
Diamondoids are cage-saturated hydrocarbon molecules and superimposable on the diamond lattice, which can be described as hydrogen-terminated nanodiamonds [1]. Adamantane, C10H16, as the smallest diamondoid, was first isolated in 1933 from crude oil [2] and synthesized chemically in 1941 by Prelog and Steinwerth [3]. Then Schleyer reported simple, efficient, and inexpensive Lewis acid-catalyzed rearrangement of endo-trimethylenenorbornane to adamantine [4]. After Schleyer’s synthesis, the availability of adamantane led to the syntheses of its derivatives and the pharmaceutical studies thereof. Aminoadamantanes constitute the birth of the medicinal chemistry of adamantane derivatives. 1-Aminoadamantane (Amantadine), a well-known antiviral drug, has been used to treat type A Influenza [5]. Antiviral activity of this amine was found gainst Rubella viruses after that thereafter [6]. Until now, eight drugs incorporating the adamantane moiety have been approved and exist in the pharmaceutical market (Figure 1). These drugs are used to treat for the treatment of acne [7], Parkinson’s [8], Alzheimer’s [9], Influenza A [5], and diabetes diseases [10]. Today adamantane motif is used mainly for modification of known drugs through an add-on strategy. The incorporation of the adamantyl moiety into the known pharmacologically active molecules has improved in many cases their pharmacological properties, without increasing toxicity. So add-on strategy resulted in many promising drug candidates incorporating an adamantane moiety [11].
Synthesis, crystal structure and antibacterial activity of zinc(II) complexes with Schiff bases derived from 5-fluorosalicylaldehyde
Published in Journal of Coordination Chemistry, 2023
Xiao-Xue Liang, Xin-Yu Zhao, Ang Guo, Xiao-Wen Wang, Mei Rong, Lin Chang, Zhong-Qiao Sun, Xu-Dong Jin
Schiff bases and their metal complexes have been widely investigated because of their biological activity [1–4]. In general, Schiff bases were prepared by a condensation of primary amines and aldehydes [5]. Amantadine and its derivatives are antiviral, preventing viruses from replicating and penetrating host cells by inhibiting M2 ion channels [6, 7]. Salicylaldehyde and its derivatives are important precursors for the synthesis of chelating ligands [8–10]. Halogenated salicylaldehyde had antibacterial and antiviral functions [11–13] and was also used for production of efficient herbicides, insecticides, and fungicides [14–16]. Fluorosalicylaldehyde showed relatively strong antitumor activity [17]. Chlorine, bromine, and iodine-substituted salicylaldehydes have been relatively more studied [18–20], while it was rarely reported that Schiff bases could be prepared from fluorosalicylaldehyde. Schiff bases have several biological activities such as anti-bacterial, anti-inflammatory, anti-tumor, and antiviral, and are good ligands [21]. Schiff base zinc(II) complexes have enhanced medicinal, catalytic, biological, antifungal, and antibacterial activities compared to ligands [22, 23]. As an extension of our previous work on metal complexes with bulky Schiff bases derived from halogenated salicylaldehyde [24, 25], in this work, we prepared three zinc(II) complexes using fluorosalicylaldehyde, bis-(2-((adamantan-1-yl)iminomethyl)-4-fluorophenolato-N,O)zinc(II) (1), bis-(2-((3,5-dimethyladamantan-1-yl)iminomethyl)-4-fluorophenolato-N,O)zinc(II) (2), and bis-(2-((3-hydroxyladamantan-1-yl)iminomethyl)-4-fluorophenolato-N,O)zinc(II) (3). The coordination behaviors of the ligands toward zinc(II) were investigated, and the structures of 1–3 were determined by single-crystal X-ray diffraction analysis.