A Novel Route to the Synthesis of Acridine Derivatives and Assay of their Antiviral Activity (original) (raw)
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An equivalent mixture of Diphenylamine and 4-chloro benzoic acid was heated in the presence of anhydrous ZnCl2 in ethanol. After few hours crude was extracted with benzene, then boiled with charcoal, filtered to get 9-(4-chlorophenyl)-acridine crystal (I). A finally powdered mixture of (I) and an appropriate amido/ imido alkylol (II) was dissolved in concentrated sulphuric acid which furnished N-[5-acridin-9-yl)-2-chlorophenyl}alkyl]-aryl amides/imides(III). Compound (III) were screened for their antimalarial activity involving the standardized method as recommended by National Committee on Clinical Laboratory Standards (NCCLS).
A review of published data on acridine derivatives with different biological activities
Kragujevac Journal of Science
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.
Acridine derivatives as anti-BVDV agents
Antiviral Research, 2011
Twenty-six 9-aminoacridine derivatives were evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of 10 RNA and DNA viruses. While seven compounds (9, 10, 14, 19, 21, 22, 24) did not affect any virus and two (6, 11) were moderately active against CVB-5 or Reo-1, 17 compounds exhibited a marked specific activity against BVDV, prototype of pestiviruses which are responsible for severe diseases of livestock. Most anti-BVDV agents showed EC 50 values in the range 0.1-8 lM, thus comparing favorably with the reference drugs ribavirine and NM 108. Some compounds, particularly those bearing a quinolizidinylalkyl side chain, displayed pronounced cytotoxicity. Further studies are warranted in order to achieve still better anti-BVDV agents, and to explore the potential antiproliferative activity of this kind of compounds.
SYNTHESIS, CHARACTERIZATION, AND ANTICANCER ACTIVITY OF SOME NOVEL ACRIDINE DERIVATIVES
Asian Journal of Pharmaceutical and Clinical Research, 2020
Objective: The objective of the study was to synthesize and evaluate the anticancer activity of some novel acridine derivatives. Methods: The present works involve condensation of acridine and various 2, 4-Thiazolidine-2,4-dione derivatives (2a-2h) with chloroacetyl chloride to give a novel acridine derivatives (5a-5l), respectively. Results: All the newly synthesized molecules (5a-5l) were characterized by FTIR, H 1-NMR, and mass spectral analysis along with physical data. The biological potentials of the new synthesized compounds are evaluated for their in vitro anticancer activity by MTT assay. Conclusion: The synthesized compounds 5a, 5f, and 5h exhibited good anticancer activity against MCF-7 and SKVO3 cancer cell lines at a concentration of 0.5 mg/mL-1 .
Antiviral chemistry & chemotherapy, 2008
In the present study, a series of N-substituted acridone derivatives was synthesized and evaluated against two haemorrhagic fever viruses (HFV). Compounds were tested against Junin virus (JUNV), an arenavirus agent of Argentine haemorrhagic fever, and dengue virus (DENV), a flavivirus agent of the most prevalent arthropod-borne viral disease in humans. Among tested compounds, two N-allyl acridones (derivatives 3c and 3f) elicited a potent and selective antiviral activity against JUNV (strain 1V4454) and DENV-2 (strain NGC) with 50% effective concentration values between 2.5 and 5.5 microM, as determined by virus yield inhibition. No cytotoxicity was detected at concentrations up to 1,000 microM, resulting in selectivity indices >181.8-400.0. Both acridones were effective against a wide spectrum of arenaviruses and the four serotypes of DENV. Furthermore, 3c and 3f failed to inactivate virus before cell infection as well as to induce a refractory state by cell pretreatment, indica...
European Journal of Medicinal Chemistry, 2006
A series of new acridines has been prepared by cyclodehydration of N-(2,3-dihydro-1,4-benzodioxin-6-yl)anthranilic acid in acidic media following classical procedures. All these compounds have in common a dioxygenated ring fused to the acridine. The tetracyclic system possesses a linear or angular structure formed by intramolecular cyclisation. The last ring and the substituent of the system modify, in an interesting way, the antitumor activity of acridines. Several of the studied compounds displayed significant cytotoxic activity (inhibition of L1210 and HT-29 cell proliferation). The most cytotoxic compound 13a, shows more activity than m-AMSA in inhibiting L1210 and HT-29 cell proliferation and this compound has been selected as a development candidate for further evaluation. The activity results also indicate that the new 11-O-substituted compounds are of considerable interest with high levels of cytotoxic activity. The angular or non-linear dioxinoacridine 10 was equiactive with the linear structure 7. Pentacyclic analogues (14 and 15) were more cytotoxic than the tetracyclic compounds (up to twofold).
Synthesis and studies of the biological activity of novel pyrimido fused acridine derivatives
Journal of the Serbian Chemical Society, 2006
Anthranilic acid was reacted with various substituted 6-bromoquinazolinones in the presence of Cu-powder and anhydrous potassium carbonate in DMF to give acid intermediates (Ullmann Type-II condensation). All these acids were then cyclized in phosphorus oxychloride to give 11-chloropyrimido[4,5-b]acridin-4(3H)-ones. All the synthesized compounds were identified by conventional methods ( 1 H-NMR, IR, elemental analysis) and were screened for their antimicrobial activity on some bacterial and fungal cultures. The results were compared with standard bactericides and fungicides. All the synthesized compounds exhibited moderate antibacterial and antifungal activity.
Synthesis and anticancer activity evaluation of some acridine derivatives
Medicinal Chemistry Research, 2014
Anticancer screening of several novel 1,2,3triazoles has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a multicomponent reaction which gave a wide access to triazole derivatives production. The synthesized compounds were tested for their anticancer activity in NCI60 cell lines. It was observed that some compounds showed remarkable anticancer activity. Two of them possessed a significant activity on leukemia, melanoma, non-small cell lung, CNS, ovarian, renal, and breast cancer. 5-Amino-1-p-tolyl-1H-[1,2,3]triazole-4-carboxylic acid (2,5-dichloro-phenyl)amide showed a significant correlation in COMPARE analysis.
Synthesis, DNA-Binding and Antiproliferative Properties of Acridine and 5-Methylacridine Derivatives
2012
Several acridine derivatives were synthesized and their anti-proliferative activity was determined. The most active molecules were derivatives of 5-methylacridine-4carboxylic 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-quadruplex structures, the most active 5-methylacridine-4-carboxamide derivatives had high affinity for DNA but showed poor specificity. An NMR titration study was performed with the most active 5-methylacridine-4-carboxamide, confirming the high affinity of this compound for both duplex and quadruplex DNAs.