Preparation of some new N-substituted 9,10-dihydroacridine derivatives

Abstract

Some new 9,10-dlhydroacrldlnes were prepared owing to the well-known central nervous system activity of the structurally related tricyclic molecules. These compounds were easily obtained from 9(10M)-acridlnones.From a biological point of view, acridine derivatives act as intercalating agents (1). Due to that, these compounds are known as anticancer drugs, like amsacrine (2) or ledakrin (3) as well as antimicrobial drugs (4,5). As intercalation directly proceeds from molecular planarity (6), any change in the molecular shape must induce the lack of the properties mentioned above, while some new properties could probably be detected because the folded acridines closely resemble the antipsychotic tricyclic drugs. Wltti reference to this, the 9,10-dihydroacridine series was studied. Some new compounds were prepared from their 9(10W)-acridinone homologues by reduction with sodium in pentanol (7). The starting 9-oxo derivatives (2) were prepared in a very good yield by phase-transfer catalysis under refluxing conditions according to the method of Nishi et al. (8). However, compound 2e was only obtained by using the method

Type 1 Phototherapeutic Agents. 2. Cancer Cell Viability and ESR Studies of Tricyclic Diarylamines

“…The diarylamines 1 – 4 , 6 , 8 , 9 , 10 , and 11 were purchased from commercial sources. The amines 5 , 7 , and 12 were prepared by published methods. − …”

Birch Reductions at Room Temperature with Alkali Metals in Silica Gel (Na2K-SG(I))

“…Some of the products (e.g., dialkylated phenazines) are attractive for photochromic and electrochromic applications . Reduced acridine derivatives are important cores of therapeutic agents that target the central nervous system …”

“…34 Reduced acridine derivatives are important cores of therapeutic agents that target the central nervous system. 35 Entries 1-3 in Table 1 show reduction of anthracene and its alkyl-and aryl-substituted derivatives. In these cases, no other byproducts were observed.…”

The reactivity of substituted 6,9-dichloracridines

“…In order to prepare the mixed solvent, the bidistillate free of СО 2 and ethanol were used. The synthesis of substituted 6,9-dichloracridines (1-9) was carried out by the method [14]; their physical and chemical parameters corresponded to the literature data [14]. CONCLUSIONS 1.…”