Synthesis of ferrocenylmethylidene and arylidene substituted camphane based compounds as potential anticancer agents

Kamenova-Nacheva, Mariana; Schröder, Maria; Pasheva, Evdokia; Slavchev, Ivaylo; Dimitrov, Vladimir; Momekov, Georgi; Nikolova, Rositsa; Shivachev, Boris; Ugrinova, Iva; Dobrikov, Georgi M.

doi:10.1039/c7nj00619e

Cited by 8 publications

(15 citation statements)

References 64 publications

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“…Other aldehydes (2-6 and 16-18) were used as commercial products. The formation and characterization of some desired ketones (22-23, 26-27) was described elsewhere, in different studies, not related to the present investigation: Grošelj et al [49] (for 22), Nevalainen et al [50] (for 23), Salisova et al [51] (for 26), Kamenova-Nacheva et al [16] (for 27).…”

Section: Chemistrymentioning

confidence: 71%

“…Bearing in mind our previous studies, it is noteworthy that arylidene camphanes exhibit enhanced cytotoxicity, depending on the nature of the arylidene moiety. [16] Thus, only compounds 40 and 55 from this study can be considered as safe for further application as antimicrobial agents (Table 3), since they preserve its low cytotoxicity even at long time treatment (72 h). Other active compounds in Table 3 (30, 41, 42, 44, 45 and 48) need further elucidation of their cytotoxicity and therapeutic windows.…”

Section: Cytotoxicity and Cell Viability Studiesmentioning

confidence: 98%

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Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons

et al. 2022

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The synthesis of 20 arylidenecamphors and 15 pyrimidines with camphane skeleton is described in the current report. A modified method for preparation of sterically hindered 2‐aminopyrimidines in two steps was demonstrated. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed different MIC values (up to 0.91 μM for ketone 39). Compound 35 demonstrated moderate (8.23 μM), but sustainable activity toward a collection of drug‐resistant M. tuberculosis strains. Many of the compounds (especially among 2‐aminopyridines 42–56) exhibited good to excellent activity against different strains of pathogenic bacteria and fungi (MIC up to 0.60 μM for compound 50), compared with reference antibiotics. Many of the newly designed compounds possess also in vitro cytotoxicity.

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Section: Chemistrymentioning

confidence: 71%

Section: Cytotoxicity and Cell Viability Studiesmentioning

confidence: 98%

Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons

et al. 2022

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“…We found that the p53 positive cancer line A549 showed a lower IC50 value, probably due to the fact that H1299 cells have a homozygous partial deletion of the p53 protein, and lack expression of p53 protein. In our previous studies, it was demonstrated that H1299 cells are less sensitive to the treatment with classical chemotherapeutic drugs such as cis-platin and Tamoxifen [22,27] as well; thus, the lack of expression of p53 is probably responsible for the observed higher drug resisters. It was interesting to examine the extent to which this cellular toxicity (mortality) is caused by the process of apoptosis.…”

Section: Discussionmentioning

confidence: 99%

“…The cytotoxic activity of CBD was tested on a panel of two human lung cancer cell lines using the MTT assay as described previously [22]. Briefly, 2000 cells were seeded into each well in 100 µL in octuplicates in 96-well flat-bottom plates and incubated for 24 h (37 °C, 5% CO 2 ) to allow attachment of the cells.…”

Section: Cell Viability Assaymentioning

confidence: 99%

The antitumor activity of cannabidiol on lung cancer cell lines A549 and H1299: the role of apoptosis

Todorova

Lazarov

Petrova

et al. 2021

Biotechnology & Biotechnological Equipment

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In the recent years, the application of new antitumor drugs has focused on the replacement of conventional chemotherapeutics with compounds derived from natural products. Cannabidiol (CBD) is one of the 113 cannabinoids derived from the plant Cannabis sativa and is characterized with complex and not entirely understood biological function. Unlike the other most abundant cannabinoid in Cannabis sativa -tetrahydrocannabinol, cannabidiol has low affinity to the endocannabinoid receptors and the manifestation of its activity does not appear to rely on the endocannabinoid system. Cannabidiol is used in the treatment of many diseases including some types of cancer. The aim of our study was to evaluate the cytotoxic activity of cannabidiol and its effect on the process of programmed cell death. This process is directly involved in the antitumor effect of many drugs. Two lung cancer cell lines, A549 expressing р53 and H1299-p53 negative, were used. Apoptosis was monitored by Anexin V assay and the activation of Caspase 3/7. We found that CBD treatment led to a dose-dependant apoptosis increase in p53 positive A549 cells. The level of apoptosis in p53 negative H1299 cells was much lower and did not seem to be dose dependent. However, the total cell viability was similar for the two cell lines, which was due to the increased necrosis observed in H1299 cells.

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“…In a study by Naik et al in 2017, a radioligand was developed with 1-adamantyl amine for PET imaging [7]. In another study done in 2017, ferrocenylmethylidene and arylidene substituted adamantane ring based compounds as potential anticancer properties were synthesized [8]. In another study, biologically active adamantyl hybrid compounds were synthesized [9].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine

Doğan

Sellitepe²,

Kahveci³

2019

Hacettepe Journal of Biology and Chemistry

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B u çalışmada, 1-adamantil amin bileşiğinin 4 farklı ester etoksikarbonil hidrazon türevi ile reaksiyonu incelenmiştir. İlk olarak, iminoester hidroklorür türevleri Pinner yöntemine göre sentezlendi. Daha sonra, ester etoksikarbonil hidrazon türevi bileşiklerinin sentezlenmesi için etil karbazat ile reaksiyona sokuldu. Son basamakta, 3-sübstitüe-4-adamantil-1,2,4triazol-5-on türevlerinin sentezlenmesi amaçlandı, ester etoksikarbonil hidrazin türevli bileşikler 1-adamantil amin ile bir yağ banyosunda kuru kuruya ısıtıldı. Ancak, IR ve ¹H-NMR analizleri ile halkanın kapanmadığı anlaşıldı ve etil N-(adamantilkarbamoil)alkilkarbohidrazonoat türevi bileşiklerin stabil ve orijinal bileşikler olarak sentezlendiği gözlenmiştir. Sentezlenen bileşiklerin yapısı, IR, ¹H-NMR, 13 C-NMR spektrumları ve LC/MS analizi gibi spektroskopik yöntemlerle kanıtlandı.

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Synthesis of ferrocenylmethylidene and arylidene substituted camphane based compounds as potential anticancer agents

Abstract: A series of new compounds with a camphane moiety was synthesized, and some of the ferrocene-containing compounds showed promising anticancer activity and selectivity.

Cited by 8 publications

References 64 publications

Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons

Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons

The antitumor activity of cannabidiol on lung cancer cell lines A549 and H1299: the role of apoptosis

Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine

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