Synthesis and biological activity of acridinyl-9-thioacetic acids and their derivatives

Gaydukevich, A. N.; Kazakov, G. P.; Kravchenko, A. A.; Porokhnyak, L. A.; Pinchuk, V. V.; Velikii, D. L.

doi:10.1007/bf01145554

Cited by 4 publications

(2 citation statements)

References 2 publications

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“…These derivatives exhibit fungicidal [1,2], anti-cancer [3][4][5], anti-parasitic [6], anti-inflammatory, and anti-microbial activities [7,8]. In addition, they are important components of effective analgesics [9,10]. Mepacrine, azacrine, proflavine, and aminacrine, are some other pharmaceutically active acridine derivatives, which also show antimalarial and antibacterial activities [11].…”

Section: Introductionmentioning

confidence: 99%

A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition

Pesyan

Akhteh

Batmani

et al. 2020

Heterocyclic Communications

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An easy and convenient technique for the one-pot synthesis of novel compounds of hexahydroacridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl) thiourea derivatives has been developed by the reaction of the octahydro-1H-xanthenes with hydroxylamine hydrochloride and thiosemicarbazide in ethylene glycol, which is a green solvent, under mild reaction conditions. IR, 1H NMR, 13C NMR spectrometry, and X-ray diffraction analysis were used to identify the structures of these compounds.

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Section: Introductionmentioning

confidence: 99%

A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition

Pesyan

Akhteh

Batmani

et al. 2020

Heterocyclic Communications

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“…Gaidukevich et al [88] synthesized acridinyl 9-thioacetic acids ( Figure 69) and their derivatives ( Figure 70) and screened them for anti-in°ammatory, analgesic and antihypoxia activities. A majority of these compounds showed anti-in°ammatory activity equal to that of indomethacin.…”

Section: Acridine Derivativesmentioning

confidence: 99%

Heterocyclic inflammation inhibitors

et al. 2004

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Non steroidal anti-in®ammatory drugs are the most widely used medicines for relief of pain. These drugs have some side e¬ects, particularly toxicity in the gastrointestinal tract and kidneys. Various approaches have been used for obtaining safer anti-in®ammatory drugs. In this review we have summarized the recent developments in the following areas; (i) Mode of action of NSAIDs, (ii) Role of COX-1 & COX-2 in in®ammation, (iii) Di¬erent approaches used to improve gastric tolerance i.e chemical manipulation, formulation & co-administration, development of non speci c (COX

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Quinacrine reactivity with prion proteins and prion-derived peptides

et al. 2013

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Quinacrine is a drug that is known to heal neuronal cell culture infected with prions, which are the causative agents of neurodegenerative diseases called transmissible spongiform encephalopathies. However, the drug fails when it is applied in vivo. In this work, we analyzed the reason for this failure. The drug was suggested to "covalently" modify the prion protein via an acridinyl exchange reaction. To investigate this hypothesis more closely, the acridine moiety of quinacrine was covalently attached to the thiol groups of cysteines belonging to prion-derived peptides and to the full-length prion protein. The labeled compounds were conveniently monitored by fluorescence and absorption spectroscopy in the ultraviolet and visible spectral regions. The acridine moiety demonstrated characteristic UV-vis spectrum, depending on the substituent at the C-9 position of the acridine ring. These results confirm that quinacrine almost exclusively reacts with the thiol groups present in proteins and peptides. The chemical reaction alters the prion properties and increases the concentration of the acridine moiety in the prion protein.

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Synthesis and biological activity of acridinyl-9-thioacetic acids and their derivatives

Cited by 4 publications

References 2 publications

A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition

A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition

Heterocyclic inflammation inhibitors

Quinacrine reactivity with prion proteins and prion-derived peptides

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