Synthesis of two novel thioacridinic derivatives and comparison of their in vitro biological activities

Mannani, Reza; Galy, Jean‐Pierre; Sharples, Derek; Barbe, Jacques; Barra, Yves

doi:10.1016/0009-2797(90)90046-p

Cited by 10 publications

(3 citation statements)

References 20 publications

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“…The reduction of the MTT dye, then, would be expected to increase with cellular metabolic activity due to elevated NAD(P)H flux. The results of the MTT assay versus the SNB-19 glioblastoma cell line on the title compounds (6) are collected in Table 1.…”

Section: Methodsmentioning

confidence: 99%

“…The biological activity of this class of compound was further elucidated to involve a ternary complex with Topoisomerase II. 2 9-Aminoacridines, such as the 9-pyridinylaminoacridines, 3 9-aminomethylacridines, 4 acridones, 5 9-thioacridines, 6 and 9-anilinoacridines 8 have been studied for their ability to intercalate DNA. These, and other, studies have verified that the proposed model of binding is valid; a strong intercalation of the acridine with duplex DNA requires that the intercalator exist as a cation under physiological conditionsm 7 be planar and aromatic, and possess substitution that is directed away from the site of intercalation.…”

Section: Introductionmentioning

confidence: 99%

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O-Benzyl-N-(9-acridinyl)hydroxylamines

Johnson¹,

Duncan²,

Mosher³

2018

Arkivoc

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A series of O-benzyl-N-(9-acridinyl)hydroxylamines was prepared, isolated, and evaluated for biological activity using both thermal denaturation and MTT assays. Changes in the thermal denaturation temperature of genomic calf-thymus DNA ranged from +6.6 °C to +20.2 °C. MTT assays on SNB-19 glioblastoma cells provided biological activity that ranged from 17.4 µM to 33.2 µM. Both evaluation methods of biological activity indicate that substitution of the benzyl group by either electron-withdrawing or electron-donating groups provides a measureable benefit in these assays. The two assays agreed on the magnitude of the interaction for each substitution pattern.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

O-Benzyl-N-(9-acridinyl)hydroxylamines

Johnson¹,

Duncan²,

Mosher³

2018

Arkivoc

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“…The new compounds tested were synthesized according to the procedure described by Mannani et al [25]. The synthetic pathway is schematized.…”

Section: Drugsmentioning

confidence: 99%

In vitro and in vivo Activities of Three Acridine Thioethers against <i>Leishmania donovani</i>

et al. 2002

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The lack of definitive chemotherapeutic agents to fight against visceral leishmaniasis has lead to the testing of numerous compounds. In the present work, we carry out an in-depth study of the activity against Leishmania donovani of three acridine derivatives both in vitro and in vivo. These compounds have proven to be highly effective at medium and high concentrations of 10 µg/ml, against both flagellate and nonflagellate forms of the parasite, which, though obtained in vitro, closely resemble natural intracellular amastigotes. The in vivo assays showed a significant reduction in the percentage of parasitation versus control, for all the compounds tested. In addition, we have studied the possible mechanism by which these acridine derivatives act: they displayed a greater inhibitory effect against macromolecule synthesis in treated flagellates, yet alterations are also caused in the production of end metabolites and in the activity of different enzymes. The data obtained indicate that the acridine derivatives had several targets, one of them is the synthesis of nucleic acids and proteins, while the second one might be interaction with the carbohydrate and energy-production processes in the parasite. This conclusion is consistent with our observations concerning the ultrastructural changes induced in the parasite by these compounds principally at the mitochondrial level.

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¹³C nuclear magnetic resonance studies of pyrazolo[α]‐9(10H)‐acridinones

Boyer

Galy

Faure

et al. 1991

Magnetic Reson in Chemistry

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13.A.-M. Hakkinen, P. Ruostesuo and S. Kurkisuo. Magn. Reson. Chem. 23, 311 (1985). 14. A.-M. Hakkinen and P. Ruostesuo, Magn. Reson. Chem. 23,424 (1 985). 15. P. Ruostesuo, A.-M. Hakkinen and T. Mattila, Magn. Reson. Chem. 25, 189 (1987). 16. A.-M. Hakkinen. P. Ruostesuo and R. Kivekas. J. Chem. Soc., Perkin Trans. 2 815 (1988). 739 (1985). Kivekas and M. R. Sundberg, J. Chem. Soc., Perkin Trans. 2 1397 (1 989). M. Engl. 17,246 (1978). KEY WORDS Pyrazolo[a] -9(1 OH)-acridinones 2-Ethylthiazolo[4,5-a]-9-acridinone lndazole derivatives 13C N M R 6 and J values

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Synthesis of two novel thioacridinic derivatives and comparison of their in vitro biological activities

Cited by 10 publications

References 20 publications

O-Benzyl-N-(9-acridinyl)hydroxylamines

O-Benzyl-N-(9-acridinyl)hydroxylamines

In vitro and in vivo Activities of Three Acridine Thioethers against <i>Leishmania donovani</i>

¹³C nuclear magnetic resonance studies of pyrazolo[α]‐9(10H)‐acridinones

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Synthesis of two novel thioacridinic derivatives and comparison of their in vitro biological activities

Cited by 10 publications

References 20 publications

O-Benzyl-N-(9-acridinyl)hydroxylamines

O-Benzyl-N-(9-acridinyl)hydroxylamines

In vitro and in vivo Activities of Three Acridine Thioethers against <i>Leishmania donovani</i>

13C nuclear magnetic resonance studies of pyrazolo[α]‐9(10H)‐acridinones

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¹³C nuclear magnetic resonance studies of pyrazolo[α]‐9(10H)‐acridinones