New analogues of AHMA as potential antitumor agents: synthesis and biological activity

“…Previous reports (CAIN et al, 1975) showed that -OCH3 group, with electron-donating effect on the aniline ring of 9-anilinoacridine derivatives, increased antitumor potency and it was suggested that replacing -CH3 group with -OCH3 may increase cytotoxicity of 5-(9acridinylamino)toluidines. CHANG et al (2003) showed that 5-(9-acridinyl-amino)toluidine derivatives with -CONHCH2CH2N(CH3)2 and -CH3 substituents at C4 and C5 of the acridine ring were more toxic than the parent AHMA (3-(9-acridinylamino)-5-hydroxymethyl-aniline), in contrast to the simple 5-(9-acridinylamino)toluidines. According to these results, it was easy to define factors that influence the cytotoxicity of 9-anilinoacridines.…”

Section: Antibacterial Activity Of Acridine Derivativesmentioning

confidence: 99%

A review of published data on acridine derivatives with different biological activities

Rupar¹,

Dobričić²,

Aleksic³

et al. 2018

Kragujevac J Science

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Acridine ring can be found in molecules used in many different spheres, including industry and medicine. Nowadays, even acridines with antibacterial activity are of research interest due to increasing bacterial resistance. Some acridine derivatives showed antimalarial or antiviral activity. Acridine derivatives were also investigated for antitumor activity due to the interaction with topoisomerase II and DNA base pairs. Considering these possible uses of acridine derivatives, this work was made as overview of all significant structure characteristics for specific action of these compounds.

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“…Compared to amsacrine, AHMA has longer half‐life in human plasma accompanied by longer duration of its drug action (Rastogi et al., 2002). AHMA was also shown to display better antitumor activity in vivo probably due to the substituent (NH 2 and CH 2 OH, Figure 1) arrangement in the meta‐positions of the aniline ring, which prevents undesired oxidation processes (Afzal, Sarfraz, Wu, Wang, & Sun, 2016; Chang et al., 2003).…”

Section: Introductionmentioning

confidence: 99%

Expedient synthesis and anticancer evaluation of dual‐action 9‐anilinoacridine methyl triazene chimeras

et al. 2020

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The efficient synthesis of molecular hybrids including a DNA‐intercalating 9‐anilinoacridine (9‐AnA) core and a methyl triazene DNA‐methylating moiety is described. Nucleophilic aromatic substitution (SNAr) and electrophilic aromatic substitution (EAS) reactions using readily accessible starting materials provide a quick entry to novel bifunctional anticancer molecules. The chimeras were evaluated for their anticancer activity. Chimera 7b presented the highest antitumor activity at low micromolar IC50 values in antiproliferative assays performed with various cancer cell lines. In comparison, compound 7b outperformed DNA‐intercalating drugs like amsacrine and AHMA. Mechanistic studies of chimera 7b suggest a dual mechanism of action: methylation of the DNA‐repairing protein MGMT associated with the triazene structural portion and Topo II inhibition by intercalation of the acridine core.

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New analogues of AHMA as potential antitumor agents: synthesis and biological activity

Cited by 22 publications

References 22 publications

Theoretical Basis, Experimental Design, and Computerized Simulation of Synergism and Antagonism in Drug Combination Studies

Theoretical Basis, Experimental Design, and Computerized Simulation of Synergism and Antagonism in Drug Combination Studies

A review of published data on acridine derivatives with different biological activities

Expedient synthesis and anticancer evaluation of dual‐action 9‐anilinoacridine methyl triazene chimeras

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