1,8-dioxo-decahydroacridines have been synthesized by the three-component reaction of aromatic aldehydes, aromatic amines (or ammonium acetate), and dimedone in the presence of sulfonic acid functionalized nanoporous silica (sba-pr-so3h) under solvent-free conditions. excellent yields, short reaction times, mild reaction conditions, and easy work-up procedures are advantages of this green method.

A Fischer indole synthesis with a cis-configurated octahydroisobenzofuran-6-one yielded exclusively a furo[3,4-c]carbazole derivative as the product of a regioselective angular annulation reaction. A Friedländer quinoline synthesis from the same substrate gave a mixture of angular and linear annulation products, i. e. furo[3,4-a]acridine and furo[3,4-b]acridine derivatives. When submitting a mi...

Oligonucleotide conjugates containing acridine and quindoline derivatives linked through a threoninol molecule were synthesized. We showed that these conjugates formed duplexes and quadruplexes with higher thermal stability than the corresponding unmodified oligonucleotides. When acridine is located in the middle of the sequence, DNA duplexes have a similar stability independently of the natura...

Several acridine derivatives were synthesized and their anti-proliferative activity was determined. The most active molecules were derivatives of 5-methylacridine-4-carboxylic acid. The DNA binding properties of the synthesized acridines were analyzed by competitive dialysis and compared with the anti-proliferative activities. While inactive acridine derivatives showed high selectivity for G-qu...

Semisynthetic aminoglycoside derivatives may provide a means to selectively target viral RNA sites, including the HIV-1 Rev response element (RRE). The design, synthesis, and evaluation of derivatives based upon neomycin B, kanamycin A, and tobramycin conjugates of 9-aminoacridine are presented. To evaluate the importance of the acridine moiety, a series of dimeric aminoglycosides as well as un...

The synthesis of RNA molecules carrying acridine or quindoline residues at their 3'- and 5'-termini is reported. These conjugates are fully characterized by MALDI-TOF mass spectrometry. Modified siRNA duplexes carrying acridine or quindoline moieties were evaluated for inhibition of the tumor necrosis factor. The conjugates showed inhibitory properties similar to those of unmodified RNA duplexe...

The mutagenic activities of benz(a)acridine, benz(c)acridine, and a number of their derivatives, including 12 epoxides and diol-epoxides, were examined in bacterial and mammalian cells to determine the importance of bay-region activation of azapolycyclic aromatic hydrocarbons. In Salmonella typhimurium strain TA98, the diastereomeric bay-region 3,4-diol-1,2-epoxides of benz(c)acridine, in which...

A series of new poly-functionalized two-carbon-tethered fused acridine/indole pairs were synthesized via Brønsted acid-promoted domino reactions between indoline-2,3-dione and C(2)-tethered indol-3-yl enaminones. The reactions were further expanded to prepare C-tethered fused acridine/pyridine pairs, N-substituted amino acids, N-cyclopropyl and N-aryl substituted fused acridine derivatives, as ...

The mutagenic activities of benz(a)acridine, benz(c)acridine, and a number of their derivatives, including 12 epoxides and diol-epoxides, were examined in bacterial and mammalian cells to determine the importance of bay-region activation of azapolycyclic aromatic hydrocarbons. In Salmonella typhimurium strain TA98, the diastereomeric bay-region 3,4-diol-1,2-epoxides of benz(c)acridine, in which...

It has been found that, like Atabrine, the phenothiazine tranquilizers promazine, chlorpromazine, promethazine, levopromethazine, and Stelazine; the antidepressants (dibenz-azepine and dibenzocycloheptene derivatives) Tofranil, Pertofrane, cyclobenzaprine, Elavil, protriptyline, and 3-chlorodibenzocycloheptene; and the acridine derivatives acridine orange, acriflavin, SKF no. 16214-A2, SKF no. ...