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Search for "cancer" in Full Text gives 508 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series
Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23
- series. Schindilactone A (68) is a nortriterpenoid isolated from Schisandraceae plant family which displayed interesting biological activities in cancer and anti-infectious axis. However, access to this compound is limited because it possesses a very complex structure composed of a highly oxygenated
- the D-ring. It was isolated in 1958 from the fungus Ophiobolus miyabeanus, and displayed a remarkable cytotoxicity against several cancer cell lines [50]. Meanwhile, variecolin (3) was isolated from the fermentation broth of the fungus Aspergillus variecolor in 1991, and it appears to be a potent
An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies
Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19
- , Sector 19, Kamla Nehru Nagar, Ghaziabad, UP, 201 002, India Cancer Biology Division, National Centre for Cell Sciences, Ganesh Khind Road, Pune-411 007, India Centre for Material Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India 10.3762/bjoc.19.19 Abstract
- configuration of each enantiomer was determined by single-crystal X-ray analysis. In addition, a one-pot synthesis of (±)-incarviditone has been achieved from rac-rengyolone by using KHMDS as a base. We have also assessed the anticancer activity of all the synthesized compounds in breast cancer cells
- on the growth of the breast cancer cell line MCF7. For instance, we did not observe the 50% growth inhibition event at 100 µM. In contrast, 5-fluorouracil potently inhibited the growth of MCF7 cells with 50% growth inhibition at 7.1 ± 0.62 µM (Figure 2). Conclusion In summary, we have successfully
Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2E,4E)-dienones
Beilstein J. Org. Chem. 2023, 19, 176–185, doi:10.3762/bjoc.19.17
- displays pronounced cytotoxicity against two human cancer cell lines [1], epicocconone (2), a fluorescent compound from the fungus Epicoccum nigrum [2], β-ionone (3) from many plant-derived sources [3], epoxysorbicillinol (4) from the saltwater culture of the fungus Trichoderma longibrachiatum separated
Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors
Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14
- , CSIC - University of Sevilla, Av. Americo Vespucio 49, 41092, Sevilla, Spain Department of Pharmaceutical Technology, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, Turkey 10.3762/bjoc.19.14 Abstract Colorectal cancer (CRC) is the third most diagnosed cancer type globally and ranks second
- in cancer-related deaths. With the current treatment possibilities, a definitive, safe, and effective treatment approach for CRC has not been presented yet. However, new drug delivery systems show promise in this field. Amphiphilic cyclodextrin-based nanocarriers are innovative and interesting
- , and furthermore in vivo antitumoral and antimetastatic efficacy in early and late-stage colon cancer models and biodistribution after single dose oral administration. This study was carried out to further elucidate oral camptothecin (CPT)-loaded amphiphilic cyclodextrin nanoparticles for the local
Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior
Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9
- mg/dL are considered hypercholesterimic. They are under high risk of cholelithiasis (formation of gallstones), atherosclerosis, heart attack, stroke, peripheral artery disease, and cancer [4][5]. Synergistic cholesterol lowering medications are inhibitors of cholesterol absorption (ezetimibe) and
- ] showed a good cytotoxic effect against the prostate cancer cell line PC-3 (Figure 2). When the spacer of I was increased from C6 to C11, the antimicrobial potential dramatically decreased [11]. In order to extend the compound platform, the synthesis of 3-azidocholest-5-ene was addressed [10]. Starting
Preparation of β-cyclodextrin/polysaccharide foams using saponin
Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7
- that saponins possess anticancer properties, by limiting proliferation and metastasis. This has been tested on different cancers such as leukemia [16], breast cancer [17] or prostate cancer to cite only a few of them [18]. They also present antimicrobial, antioxidant, anti-inflammatory, antidiabetic
- potential uses can be either for oral delivery targeting intestine [33] or for an anti-skin cancer treatment [35], for example. This complexation step is also interesting for the synthesis of molecular imprinted polymers containing cyclodextrin [36]. In previous works, we have produced crosslinked
Combining the best of both worlds: radical-based divergent total synthesis
Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1
- 2021) [37]: Dysideanone B (75), isolated from the South China Sea sponge Dysidea avara, possesses an unprecedented 6/6/6/6-fused tetracycle with interesting anticancer properties against HeLa and HepG2 cancer cell lines (Scheme 6) [38]. The structurally similar dysiherbols 79 and 80, bearing a 6/6/5/6
- -fused tetracycle instead, were reported to possess NF-kB-inhibitory activity and anticancer activity against NCI H-929 cancer cell lines (Scheme 6) [39]. In 2021 Lu’s group reported the total synthesis of members of both meroterpenoid families based on a highly chemoselective α-alkylation in the
A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
Beilstein J. Org. Chem. 2022, 18, 1649–1655, doi:10.3762/bjoc.18.177
- adenocarcinoma) and NCI-H460 (lung cancer) cell lines and proved completely non-cytotoxic. This validates these new compounds as suitable molecular probes for interrogating various biological targets via screening in cell-based assays. Conclusion We have developed a straightforward access to novel spiro
A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction
Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175
- fragments in the structure of compound 5a) include compound 6 for the treatment of cognitive impairment [7], BET bromodomain inhibitors 7 [8] and 8 [9] for cancer treatment, σ1 receptor modulator 9 for diverse disorders [10] and bacterial regulatory RNA binder 10 [11] (scaffold A) as well as antidiuretic 11
- although the yield of product 21 was diminished compared to that of unsubstituted compound 5a. The structure of compound 21 was also confirmed by the single-crystal X-ray analysis (Scheme 3). All compounds were tested against lung cancer cell lines A549 and NCI-H460 and did not show any appreciable effect
One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171
- Chemical Engineering, University of North Dakota, 241 Centennial Drive Stop 7101, Grand Forks, North Dakota 58202, United States Department of Cancer Biology, Dana-Farber Cancer Institute, Harvard University, Boston, MA 02215, USA Broad Institute of Harvard and MIT, Cambridge, MA 02142, United States
Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library
Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164
- , fragmentation of the mitochondrial tubular network, chromosome misalignment, and cell cycle arrest in mitosis in LNCaP prostate cancer cells [38]. The bastadin structure class is well-documented within the literature for their cytotoxic activity [37][39][40][41], with both bastadins 4 and 8 exhibiting in vitro
Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme
Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144
- efficient modulators of 14-3-3 protein–protein interactions (PPIs) [3][4]. 14-3-3 PPIs, which refer to the binding interactions of 14-3-3 proteins with hundreds of “client” proteins, are associated with many diseases, such as cancer and neurodegenerative diseases [3][4]. As a result, lots of attempts
On drug discovery against infectious diseases and academic medicinal chemistry contributions
Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141
Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups
Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137
- role in several human diseases including cancer and neurodegenerative disorders like Alzheimer’s and Parkinson’s diseases [5]. Based on these observations and findings it is not surprising that the 14-3-3 family has attracted interest in pharmacological research as a novel potential target [5][6]. One
- -3-3ζ homodimer [14]. Very recently the survivin–histone H3 interaction was disrupted using a GCP dimer, which led to decreased cancer cell proliferation [8]. A major problem in this context is the readout of binding events, which is currently mainly achieved by indirect measurements. One approach to
Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones
Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118
- also important substructures in a variety of non-natural compounds and their pharmacological effects against bacteria [13][14][15][16], inflammation [17][18], viruses [19], radical [20], and cancer [21][22][23][24][25][26] have been proven. It is undoubtedly true that heterocyclic compounds containing
Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold
Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109
- readily available 3(2H)-isoquinolones followed by TfOH-promoted hydroarylation by an arene molecule. Screening of the novel 1,2,4-trisubstituted 1,4-DHIQs against cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigations as anticancer
- -DHIQ adducts synthesized in this work, they were deemed efficient probes for the perturbation of vital cellular targets. Screening of these compounds against lung carcinoma cancer cell lines confirmed high cytotoxicity of selected analogs, which validates this new chemotype for further investigation as
Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids
Beilstein J. Org. Chem. 2022, 18, 837–844, doi:10.3762/bjoc.18.84
- also been shown to play a significant role in pathologies such as cancer, neurodegenerative diseases, and metabolic disorders [1][2]. HDACs are structurally divided into 18 isoforms, which are grouped into 4 classes. The 11 isoforms belonging to classes I, II, and IV are dependent on the Zn2+ ion in
Terpenoids from Glechoma hederacea var. longituba and their biological activities
Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58
- , nerve growth factor (NGF) secretion stimulation activities in C6 glioma cells, and cytotoxic activities against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15). Compounds 2 and 5–7 exhibited inhibitory effects on the NO production with IC50 values of 52.21, 47.90, 61.61, and 25.35 μM
- inhibitory activities, compound 5 showed a stronger stimulating effect on the secretion of NGF than compound 4 (76.56 ± 6.51%). Cytotoxic effects of compounds 1–9 against four human cancer cell lines [non-small-cell lung adenocarcinoma (A549), malignant ovarian ascites (SK-OV-3), skin melanoma (SK-MEL-2
- . Compounds 7 and 9 showed selective cytotoxic activities against human cancer cell lines. This study suggests that the bioactive tepenoids (2, 5–7, and 9) from G. hederacea var. longituba would be potential new drug candidates. Experimental General experimental procedures. Optical rotations were measured on
Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery
Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56
- molecule overexpressed in cancer cells, through host–guest competitive substitution since TBTQ-CB6 has a stronger binding affinity toward SM than MV and DOX. The host–guest interactions of the complexes of TBTQ-CB6 with MV, DOX and SM were investigated by NMR spectroscopy and fluorescence spectroscopy. The
- cancer treatment [1][2]. Many types of chemotherapeutic drugs have been commonly used in clinical practice, including doxorubicin (DOX) [3], chlorambucil [4], oxaliplatin [5], etc. However, the use of most chemotherapeutic agents is often challenged by their poor water solubility and non-selective
- targeting of cancer cells, resulting in low bioavailability and systemic side effects [6]. To address these drawbacks, various approaches have been developed to improve the bioavailability of these and other drugs and to enable their targeted delivery to cancer cells [7][8][9][10]. In recent years
Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold
Beilstein J. Org. Chem. 2022, 18, 533–538, doi:10.3762/bjoc.18.55
- interactions, including oncogenic ones [18]. As the first step towards biological characterization of compounds 2, they were screened for cytotoxicity against the A549 human lung adenocarcinoma cell line. Among the eleven compounds, N-aryl analogs 2a–e, 2h, and 2j had no effect on the cancer cell viability
Menadione: a platform and a target to valuable compounds synthesis
Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43
- menadione, a synthetic naphthoquinone belonging to the vitamin K group. This compound can be synthesized by different methods and it has a broad range of biological and synthetic applications, which will be highlighted in this review. Keywords: cancer; chemical reactions; 2-methyl-1,4-naphthoquinone
Four bioactive new steroids from the soft coral Lobophytum pauciflorum collected in South China Sea
Beilstein J. Org. Chem. 2022, 18, 374–380, doi:10.3762/bjoc.18.42
- , demethylgorgosterol [9][10]. Thus, the structure of compound 4 was assigned as shown in Figure 1. Biological activity The cytotoxic activities of compounds 1–7 were evaluated against three cancer cell lines (HL-60, K562, and Hela), but only compound 1 exhibited weak cytotoxic activity against K562 cells with an IC50
Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity
Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29
- labeling proteins and visualizing cancer due to the ability of s-tetrazine to fast and biocompatible ligation with alkenes via the inverse electron demand Diels–Alder reactions [29][30][31]. At the same time, azolo-annulated 1,2,4,5-tetrazines remain to be a scarcely studied class of compounds, mainly due
Synthesis and bioactivity of pyrrole-conjugated phosphopeptides
Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17
- Qiuxin Zhang Weiyi Tan Bing Xu Department of Chemistry, Brandeis University, 415 South Street, Waltham, MA 02454, USA 10.3762/bjoc.18.17 Abstract Here we report the synthesis and effect on the cell viability of pyrrole-conjugated phosphopeptides. Encouraged by the selective inhibition of cancer
- , such as intracellular phase transition [22], molecular imaging [23][24][25][26][27][28][29][30][31][32][33], anisotropic hydrogels [34][35], targeting subcellular organelles [36][37][38][39][40], elimination of pluripotent stem cells (PSC) [41][42], and cancer therapy [43][44][45][46][47][48][49][50
- a variety of phosphopeptides that selectively inhibit cancer cells [38][64][65][71][72]. Encouraged by the results from the naphthylacetyl capped phosphopeptides, we decided to use multiple N-methylpyrroles, as the heteroaromatic analog of naphthyl, to cap the N-terminal of phosphopeptides for EISA
Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction
Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15
- kinases (Cdks), which are potential targets for cancer chemotherapy. Herein we report an efficient and clean pathway to the fourth isomer, which remained elusive so far, namely 7,8-dihydroindolo[2,3-d][1]benzazepin-6(5H)-one. Moreover, we demonstrate the generality of our pathway by synthesizing two
- unit is shifted and the indole ring is flipped (D). Isomer D has been shown to be a potent tubulin-polymerase inhibitor, while B was only mildly cytotoxic towards cancer cells at a concentration of 1 µM [5][6]. Backbone C, despite being very similar to the other three scaffolds, remained a synthetic
- nanomolar concentration range and selectivity for cancer cells over normal ones [22]. The synthesis of core structures A, B, and D is well-documented in the literature [2][6]. Herein we describe the first synthesis of 7,8-dihydroindolo[2,3-d][1]benzazepin-6(5H)-one (C) (Figure 1). Results and Discussion
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