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Search for "cytotoxic activity" in Full Text gives 91 result(s) in Beilstein Journal of Organic Chemistry.
Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities
Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48
- methacryloyl chloride, cinnamoyl chloride, 4-bromobenzoyl chloride, trans-2-methyl-2-butenoyl chloride, and crotonyl chloride. These compounds were evaluated for their cytotoxic activity against the murine fibroblasts L929, human cervix carcinoma KB-3-1, human lung carcinoma A549, human prostate cancer PC-3
- nematicidal activity with LD90 and LD50 of 100 and 12.5 µg/mL, respectively. Since the parent compound was not active, the present study supports the fact that the acylation reaction can improve bioactivities of some natural products. Keywords: acylation reaction; cytotoxic activity; massarilactone D
- prostate cancer PC-3, epidermoid carcinoma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Although the parent compound was not active as previously described [15][16], compounds 2 and 3 exhibited a significant cytotoxic activity against all the tested cells lines with IC50 values
Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones
Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26
- -(1,1-Dimethyl-1H-benzo[e]indolin-2-yl)-5,6,7-trichloro-1,3-tropolone exhibited high in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines. Keywords: cytotoxic activity; fluorescence; o-chloranil; quantum chemical DFT calculations; 1,3-tropolones; X-ray diffraction
- antibacterial [4] and cytotoxic activity [6][7]. Existing approaches to the synthesis of 1,3-tropolone derivatives have a number of drawbacks, namely, limited synthesis methodology and low yields of the target compounds [8][9][10][11][12][13][14][15]. Over the past decade, only a few reports have been published
- properties towards CN− and Hg2+ ions and evaluation of in vitro cytotoxic activity against A431 skin cancer and H1299 lung cancer cell lines. Results and Discussion We found that boiling of equimolar amounts of benzannelated 2,3,3-trimethylindolenines 2a,b and o-chloranil (3) (method A) in dioxane leads to
Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia
Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23
- the first 2-pyridone derivative, farinosone A (2) that through N-hydroxylation would reveal farinosone B (3). Biological evaluation All the isolated compounds were assessed for their cytotoxic activity against a panel of seven different cancer cell lines. The results (Table 2) revealed that farinosone
- B (3) and beauvericins A–C (4–6) possess potent significant cytotoxic activities against all tested cell lines with IC50 values ranging from 0.2 to 6.2 µM, whereas farinosones D (1) and A (2) revealed weak to no cytotoxic activity. These results suggested that compounds 3–6 could be considered as
Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina
Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267
- ceratinadin G (1) was evaluated against L1210 murine leukemia cells and KB epidermoid carcinoma cells. Ceratinadin G (1) showed moderate cytotoxic activity against L1210 cells (IC50 = 4.7 μM) and KB cells (IC50 = 15.1 μM). Conclusion Ceratinadin G (1) is the first psammaplysin derivative identified to contain
Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction
Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256
- aimed at inhibiting tubulin assembly, N-mesyl-2-(1-phenylvinyl)indoles were active against HCT-116 cells on the order of a GI50 of 10 mM, although the mechanism originally sought was not demonstrated [39]. Therefore, in this work, the cytotoxic activity of methanesulfonylindoles 18a–j was explored
- relevant for the cytotoxic activity. The 1,5-disubstituted tetrazole-1,2,3-triazole hybrids synthesized by our group [26] had similar effects to the present compounds, suggesting that 1,5-disubstituted tetrazole and indole are pharmacophoric fragments with significant biological and pharmacological
- reaction is utilized as a post-Ugi-azide reaction, using propargylamine as a key bifunctional reagent. The results of cytotoxic activity were moderate. However, the information obtained from this study, together with that obtained with previously described analogs, provide important information for
N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity
Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240
- cytotoxic activity against melanoma and squamous cell carcinoma cells, lung cancer and glioblastoma cells [30]. It was shown in a WST-1 assay that these compounds exhibit a concentration-dependent inhibition of the metabolic activity of A375 and A431 cells, while the non-glycosylated derivative 34 proved to
- mitochondria was changed. The presence of β-33b provoked a significant upregulation of the enzyme heme oxygenase-1. In conclusion, mitochondria are attacked by compound β-33b in the context of its cytotoxic activity against skin cancer cells. Aglycon 35 again proved to be inactive in all assays. It was
- deprotection with NaOMe afforded β-81a in 98% yield. Likewise, rhamnosides β-81b,c mannosides β-81d–f, and glucoside β-80g were obtained in good yields. Some products exhibited weak cytotoxic activity against human ceratinocytes (HaCaT). However, in contrast to many indirubin-N-glycosides and their analogues
Natural resorcylic lactones derived from alternariol
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
- -methylalternariol derivative 15 was isolated from A. alternata and showed inhibitory activity against HCV NS3/4A protease (IC50: 52.0 μg/mL), cytotoxic activity against HEP-G2 cancer cells, and turned out to be antibacterial against Bacillus cereus, B. megaterium, and Escherichia coli with inhibition zones of 17
- determined by NMR spectroscopy and unambiguously confirmed by total syntheses [44][177]. It showed cytotoxic activity against SW1116 cells with an IC50 value of 12 μg/mL [168]. Chlorinated alternariol derivatives (Figure 9) together with the respective redox-modified natural products (Figure 20, vide infra
- ]. Its structure was confirmed by total syntheses [179][182][183]. Graphislactone G showed a significant cytotoxic activity against SW1116 cells with an IC50 value of 21 μg/mL [168]. Penicilliumolide D (29), the 2-chlorinated derivative of graphislactone A (vide supra), was first isolated from
Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps
Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178
- , product 17a shows cytotoxic activity against Hep G2 hepatocellular carcinoma and MCF-7 breast carcinoma cell lines. The synthesis of 3,5-bis(arylamino)pyrazoles 21 involves the preparation of bisarylthioamides 22 via nucleophilic addition and double retro-Claisen condensation of isothiocyanates 19 and
Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA
Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167
- activity and thus block cancer formation [2]. Alangiumkaloids A, an isoquinolinone alkaloid isolated from Alangium salviiforlium, was reported to exhibit cytotoxic activity against cancer cells [3]. In 2018, duvelisib, a dual inhibitor of phosphoinositide-3 kinases, was firstly approved by the FDA for the
Syntheses and medicinal chemistry of spiro heterocyclic steroids
Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152
- their antiproliferative activity against a panel of cancer cells, in which the activity of some compounds was close to that of cis-platinum in some cell lines. It should be noted that N-propylamide derivatives showed low cytotoxicity on cancer cells. Additionally, 167c did not present cytotoxic activity
Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry
Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147
- member of the channel-forming, cytotoxic proteusins. It is biosynthesised by Microvirgula aerodenitrificans. Like polytheonamide B, aeronamide A shows cytotoxic activity against HeLa cells, with an IC50 of 1.48 nM. AerE, the PoyE homologue, installs five methylations on the amides of Asn25, Asn31, Asn37
Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction
Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99
- achieved. Under both conditions, virtually no product mixtures were observed. Preliminary biological evaluation To investigate the cytotoxic activity of the indanone derivatives, in total 20 compounds were tested at a concentration of 5 and 50 μg/mL for 72 h in a panel of four histologically unrelated
Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines
Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3
- experimentally observed. The base-catalyzed cycloaddition of 3,3-diaminoacrylonitriles 1 to azides 2, thus proceeds in a Cornforth-type fashion, which involves a triazole–triazole isomerization through ring opening, rotation of the amidine substituent around the single bond, and cyclization. Cytotoxic activity
- The cytotoxic activity of seven synthesized compounds 3b,d,e,g,h,l,m was studied. According to the results of the MTT test, IC50 values were calculated for these compounds (Table 2). The results obtained indicated that compounds 3b,e,g,h did not have a pronounced effect on the viability of cultured
Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea
Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84
- inducing cytotoxicity. In addition, another study demonstrated that a lanostanoid glycoside derivative with a glucosyl ester at the C-21 carboxylic acid group was active in a cytotoxic activity assay, whereas the galactosyl ester counterpart was inactive [36]. Similarly, the carboxylic acid group at C-21
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
New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling
Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161
- drug for its treatment, however, its clinical use has been limited due to its side effects. Here, we designed two new nitroaryl-1,2,3-triazole triterpene derivatives as novel anti-RSV drugs. Their anti-RSV and cytotoxic activity were evaluated in vitro, RSV protein F gene effects by RT-PCR and
New azodyrecins identified by a genome mining-directed reactivity-based screening
Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102
- previous report demonstrated the cytotoxic activity of azodyrecins [21]; however, the relationships between the structure and cytotoxicity were not determined. With new azodyrecin analogs with saturated alkyl chains in hand, we attempted to gain insights into the effects of the double bond on cytotoxicity
Terpenoids from Glechoma hederacea var. longituba and their biological activities
Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58
- , respectively. Compound 5 also exhibited a significant stimulating effect on NGF secretion (122.77 ± 8.10%). Compound 9 showed potent cytotoxic activity against SK-OV-3 (IC50 = 3.76 μM) and SK-MEL-2 (IC50 = 1.48 μM) cell lines, while 7 displayed a strong cytotoxic activity against the SK-MEL-2 (IC50 = 9.81 μM
- ), and colon adenocarcinoma (HCT15)] were also investigated using a sulforhodamine B (SRB) bioassay (Table 6). Compound 9 showed selective cytotoxic activities against SK-OV-3 and SK-MEL-2 cell lines, with IC50 values of 3.76 and 1.48 μM, respectively. Compound 7 also displayed a cytotoxic activity
- ) as ᴅ-glucopyranoside. GC–MS analysis was perfomed under the following conditions: capillary column, HP-5MS UI (30 m × 0.25 mm × 0.25 μm, Agilent); column temperature, 230 °C; injection temperature, 250 °C; flow rate, 1.0 mL/min; carrier gas, N2 [22]. Cytotoxic activity, NO production, NGF secretion
Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities
Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54
- ± 0.04 µM (100 ng/mL, 200 nM), respectively. Two compounds (3b and 10d) have also been tested for anti-SARS-CoV-2, antibacterial, and cytotoxic activity. Keywords: antimalarial activity; anti-SARS-CoV-2 activity; chloroquine; 2-nitroperchlorobutadiene; nucleophilic vinylic substitution; 1H-pyrazoles
Sesquiterpenes from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346
Beilstein J. Org. Chem. 2022, 18, 479–485, doi:10.3762/bjoc.18.50
- . Compound 2 possesses a rare bicyclic sesquiterpene skeleton. The antimicrobial and cytotoxic activities of the isolated compounds were evaluated. Keywords: antimicrobial activity; cytotoxic activity; γ-lactone; soil-derived fungus; sesquiterpene; Trichoderma citrinoviride; Introduction The fungus
- amount were evaluated for their antibacterial activity against S. aureus ATCC25923 and methicillin-resistant S. aureus SK1, antifungal activity against C. neoformans ATCC90113 as well as cytotoxic activity against KB, MCF-7, and noncancerous Vero (African green monkey kidney fibroblast) cells. None of
- support. Finally, National Center for Genetic Engineering and Biotechnology (BIOTEC) is acknowledged for evaluation of cytotoxic activity. Funding This work was supported by the NSTDA Chair Professor grant (the Fourth Grant) of the Crown Property Bureau.
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
- methyl group at C-4. The absolute configuration of 1–3 was determined by X-ray diffraction analyses. Compounds 1–7 were subjected to a cytotoxic activity evaluation against HL-60, K562, and Hela cells, only compound 1 exhibited weak cytotoxic activity against K562 cells with an IC50 value of 19.03 μM. In
Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents
Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206
- ). The EGFR inhibitor drugs bearing the 4-anilinoquinazoline moiety did not show potent cytotoxic activity against T98G cells (21.3 µM for erlotinib, and 37.8 µM for gefitinib). However, the tubulin polymerization inhibitor (verubulin), which contains 4-anilinoquinazoline in its chemical structure, was
Strategies for the synthesis of brevipolides
Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157
- [4]. These compounds demonstrated cytotoxicity against various human cancer cells. Additionally, the research group led by Pereda-Miranda later isolated more members of brevipolide (1–15) from the same plant during 2013–2017 and further confirmed the cytotoxic activity of these natural products [1
(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia
Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144
- , 2c, 2d, and 2g with the BCR-Abl-1 structure (PDB code: 3PYY), showing steric interactions (red dotted lines) and hydrogen bonds (blue dotted lines). Synthetic route of the triazole derivatives 1a,b, and 2a–j. Cytotoxic activity, confidence interval, and selectivity index of imatinib and derivatives
N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles
Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86
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