Crystal structure of 2-(methylamino)tropone

Vuuren, Ludwig Jansen van; Visser, Hendrik G.; Schutte‐Smith, Marietjie

doi:10.1107/s2056989019009502

Cited by 3 publications

(4 citation statements)

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“…В ряде исследований продемонстрирована высокая противоопухолевая эффективность трополонов в сочетании с их минимальным воздействием на нормальные ткани и низкой токсичностью, что делает данную группу соединений перспективной [18]. В настоящее время наиболее изученным трополоном является хиноктиол (β-туяплицин), проявляющий высокую противоопухолевую активность по отношению к различным культурам опухолевых клеток [19,20].…”

Section: Discussionunclassified

Evaluation of the cytotoxic activity and toxicity of a tropolone derivative with a potential antitumor effect

Lukbanova¹,

Sayapin

Gusakov

et al. 2022

Bûll. sib. med.

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The aim. To study the toxicity of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone in vitro and in vivo.Materials and methods. 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone was synthesized using a method for expanding the o-quinone cycle during the reaction between 5-nitro-2,6,8-trimethyl4-chloroquinoline and 3,4,5,6-tetrachloro-1,2-benzoquinone while boiled in dioxane. An in vitro experiment was carried out in the human A549 cell line. Cell viability was assessed using the MTT colorimetric assay by reducing the optical density of the experimental samples compared with the control ones. Acute toxicity was studied on 20 BALB/c Nude male mice. The test compound was administered once orally as a suspension in 1% starch gel at three doses: 0.0055 (group 1), 0.055 (group 2) and 0.55 mg / g (group 3). The control group (group 4) received a placebo.Results. We synthesized a new compound, 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone. Its structure was established by 1 H nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, and mass spectrometry. The yield was 19.8 g (52%), the melting point was 205–207 ºС, bright yellow crystals (benzene) were observed. The half-maximal inhibitory concentration (IC50) of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone was 0.21 ± 0.01 μM, which was significantly lower (р < 0.05) than the IC50 of cisplatin (3.84 ± 0.23). Following the in vivo experiment, no toxic effect of tropolone was detected when administered once at a dose of 0.0055, 0.055, and 0.55 mg / g. Conclusion. 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone demonstrated cytotoxic effects on the A549 cell line at a lower IC50 than cisplatin which is widely used in treatment of cancers, including lung cancer. Insolubility of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone in water and the absence of its toxic effect in the studied modes determine the scope of its application for further study of cumulative and antitumor effects.

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Section: Discussionunclassified

Evaluation of the cytotoxic activity and toxicity of a tropolone derivative with a potential antitumor effect

Lukbanova¹,

Sayapin

Gusakov

et al. 2022

Bûll. sib. med.

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“…К перспективным ингибиторам опухолевого роста относят алкалоиды трополонового ряда. Это семичленные небензоидные ароматические соединения с разнообразными видами биологической активности [10,12,13]. Цитотоксическое действие трополонов в отношении опухолевых клеток млекопитающих обнаружено J.S.…”

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“…Whitehouse показали способность 2-гидрокси-4-изопропил-2,4,6-циклохепа-триена-1 ингибировать процессы окислительного фосфорилирования [15]. Однако вопрос о спектре и механизмах противоопухолевой активности трополонов не утратил своей актуальности вплоть до настоящего времени [13,16].…”

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Assessment of an antitumor effect of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone in A-549 tumor cell subcutaneous xenografts

Lukbanova¹,

Zaikina²,

Sayapin

et al. 2021

Alʹm. klin. med.

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Rationale: Chemotherapy is one of the lung cancer treatment methods. The search for new substances with antitumor effect against malignant lung neoplasms is relevant because of low efficacy and side effects of cytotoxic agents. A promising substance class with various biological activities, including antitumor, includes alkaloids of the tropolone family, such as heptamerous non-benzoid aromatic compounds. 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)- 5,6,7-trichloro-1,3-tropolone has been synthesized in Institute of Physical and Organic Chemistry; it is a new compound belonging to 2-quinoline-2-yl derivatives of 1,3-tropolone.Aim: To assess the antitumor effect of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)- 5,6,7-trichloro-1,3-tropolone on subcutaneous xenografts of A-549 lung tumor cells in immunodeficient Balb/c Nude mice.Materials and methods: The study included 50 immunodeficient Balb/c Nude mice divided into 4 experimental groups depending on the dosage of the study substance (0.0055, 0.055, 0.55, and 2.75 mg/g); group 5 was the control group. A-549 cells of lung cancer were used as a xenograft. The antitumor effect of tropolone was evaluated by the inhibition of tumor growth and the index of tumor growth. The experiment lasted for 36 days starting from the first administration of the substances.Results: The mean tumor volumes on day 36 of the experiment in the control group and four experimental groups were 2729.5; 2150.8; 1746.4; 952.3 and 678.9 mm3 , respectively. The indices of tumor growth in groups 1, 2, 3 and 4 were significantly lower than in group 5 (control) starting from days 24, 21, 21 and 15, respectively, and till the end of the experiment. Maximal differences between groups 4 and 5 were observed at days 33 and 36 (by 3.7, p=0.01 and 4.1, p=0.003 times, respectively).Discussion: The anti-tumor effect of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)- 5,6,7-trichloro-1,3-tropolone demonstrated in the study could be related to various mechanisms. For example, numerous studies have shown that its related compound hinokitiol exerts a cytotoxic effect associated with cessation of the cell cycle, apoptosis induction, DNA damage, and autophagic death of tumor cells.Conclusion: The study demonstrated significant differences in xenograft volumes in all experimental groups, compared to the control group. In mice, 2.75 mg/g bodyweight was the most effective dosage of the studied compound leading to a slow decrease in tumor growth rates and a decrease in the volumes of subcutaneous xenografts.

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“…the rings generated through hydrogen bonding are significantly smaller. In addition, two examples of hydrogen-bonded coordination polymers and two monomeric species have been reported in the literature [14,[43][44][45].…”

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confidence: 99%

Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C₁₉H₁₆N₂OS

Hanft

Lichtenberg

2020

Zeitschrift Für Kristallographie - New Crystal Structures

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Crystal structure of 2-(methylamino)tropone

Cited by 3 publications

References 38 publications

Evaluation of the cytotoxic activity and toxicity of a tropolone derivative with a potential antitumor effect

Evaluation of the cytotoxic activity and toxicity of a tropolone derivative with a potential antitumor effect

Assessment of an antitumor effect of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone in A-549 tumor cell subcutaneous xenografts

Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C₁₉H₁₆N₂OS

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Crystal structure of 2-(methylamino)tropone

Cited by 3 publications

References 38 publications

Evaluation of the cytotoxic activity and toxicity of a tropolone derivative with a potential antitumor effect

Evaluation of the cytotoxic activity and toxicity of a tropolone derivative with a potential antitumor effect

Assessment of an antitumor effect of 2-(6,8-dimethyl-5-nitro-4-chloroquinoline-2-yl)-5,6,7-trichloro-1,3-tropolone in A-549 tumor cell subcutaneous xenografts

Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C19H16N2OS

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Dimerization of 2-[(2-((2-aminophenyl)thio)phenyl)amino]-cyclohepta-2,4,6-trien-1-one through hydrogen bonding, C₁₉H₁₆N₂OS