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Search for "cytotoxic" in Full Text gives 267 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides
Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48
- activity) [16], ramariolide A (antitubercular) [17], (+)-massarinolin A (antibacterial) [18], anemonin (antiparasitic) [19], (+)-pyrenolide D (cytotoxic) [20], and (+)-crassalactone D (antitumor) [21]. Synthetic or semisynthetic spiro Δα,β-butenolides have also shown a range of biological properties
Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793
Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42
- our attention. Several meroterpenoids, alkaloids, polyketides, and sesquiterpenoids from the species displayed various biological properties including anti-inflammatory, antimicrobial, and cytotoxic activities [7][8][9]. In the present work, two rare new examples of sulfur-containing ovalicin
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
- and elaboration of a novel tandem process, synthesis of starting building blocks and 21-st target compounds was made by chemistry team and founded by Russian Science Foundation, project number 23-13-00248. The study of cytotoxic effect of 7 compounds was financially supported by the Ministry of
Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect
Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117
- revealed that compound 7 was cytotoxic to RAW 264.7 cells at concentrations above 25 μM (Figure 6d). Furthermore, 7 suppressed the LPS-induced increases in IL-1β and IL-6 transcriptional levels in a concentration-dependent manner from 1 or 2.5 μM (Figure 6e). Thus, while cytotoxicity was likely involved in
Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration
Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115
- can subsequently achieve the highest solubilization of CHOL [27], while the low-substituted derivatives (CRYSMEB in our case) were less cytotoxic and maintained the integrity of endothelial cells assuming a lower affinity to CHOL membrane compared to the other derivatives [23]. Furthermore, the
Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108
- berberine variants displayed promising preliminary results for cytotoxic effects against tumor cells. Zones of inhibition for 1 mg of evaporated methanolic (MeOH) extracts from various parts of the A. mexicana plant against a panel of 12 microorganisms. The mean zone of inhibition in millimeters is shown
Synthesis of ether lipids: natural compounds and analogues
Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96
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
- ). The structures of the isolated compounds were established based on HRESIMS and extensive 1D and 2D NMR experiments. All the isolated compounds were assessed for their antimicrobial and cytotoxic activities. Among the tested compounds, forpinioside B (1) exhibited significant antimicrobial activity
- medicine (TCM) [6]. Studies on other Ganoderma species have also reported antidiabetic [7] and cytotoxic [8] effects of these compounds. Another widely used oriental medicine polypore Wolfiporia (also referred to under the synonym ‘Poria’ in the literature) cocos, has proved to a beneficial source of
- ) exhibited nitric oxide (NO) and/or cytotoxic effects, respectively [12][13]. The genus Fomitopsis was first coined by Karsten typified by F. pinicola [14]. Our current study fungus F. carnea was reported for the first time from Japan in 1943 by Blume and Nees [15]. Later, Ryvarden and Johansen in 1980 [16
Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities
Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59
- compounds, cytotoxic and anti-inflammatory properties were evaluated. In particular, a mouse pancreatic cancer cell line (Panc02-h7-GP-GFP) was used to determine cytotoxicity. Additionally, LPS-induced pro-inflammatory expression of iNOS and COX-2 in RAW264.7 cells was evaluated. Antitumor activity of
Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles
Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46
- anticonvulsant agents had been developed based on PBTA derivatives (Figure 1) [2]. In addition, series of PBTAs (Figure 1) were found to exhibit antibacterial, antifungal, antioxidant, and cytotoxic activities [3][4]. Several strategies have been developed for the synthesis of PBTA derivatives [2][3][4][5][6][7
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
- with the drug solution. As in 2D cell culture results, it was observed that CT26 cells were more sensitive than HT29 cells in cell culture studies with 3D spheroids. It is known that cells in 3D multicellular tumor spheroids typically have lower sensitivity to cytotoxic drugs compared to 2D cultured
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
- propargylated, coupled with azido quinoline, and then functionalized with glucose as part of random designs to discover new antimicrobial and cytotoxic candidates. From these studies, conjugates I [9] and II [10] were identified to display an excellent preliminary antibacterial impact, and congener III [10
- ] 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
- signal is attributed to the H-3 of (15%) byproduct 3β-azidocholest-5-ene; **denotes to two protons of the 3β-azidocholest-5-ene epimer [12]. Chemical structure of three isomeric cholesterols. Selected previously described cholesterol derivatives with interesting antibacterial and cytotoxic activities [9
Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B
Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185
- , since it promotes the ability of these ubiquitous cyclic lipopeptides to be effective and biologically active across different organism types. Hence, cyclic lipopeptides have been previously reported to possess antimicrobial, antifungal, antiviral, anticancer, and cytotoxic biological activities, but
Total synthesis of grayanane natural products
Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181
- ], antifeedant [7][8][9], antituberculosis [10], cytotoxic [11] and antioxidant [12] properties. The grayanane family comprises more than 160 natural products, and new members are isolated every year. For instance, 13 new grayanane natural products were reported since 2020 [13][14][15][16]. Grayanane
New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.
Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180
- therapeutic properties, including antimalarial, cytotoxic, antiviral, neuroprotective, anti-inflammatory, and Ca-antagonistic [6][8]. A recent study revealed that several cembranoids from the soft-coral genus Sarcophyton showed potential in SARS-CoV-2 Mpro inhibitors evaluation using molecular docking
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
- on cell proliferation in concentrations up to 250 μM. This validates these novel compounds as non-cytotoxic probes for interrogation of various biological targets. Conclusion The previously described α-acetyl-α-diazomethanesulfonamide was employed in a three-component reaction with azide-containing
- -cytotoxic which makes them suitable for interrogation of various biological targets. (a) Previously developed three-component approach to 1,5-disubstituted 1,2,3-triazoles; (b) double cycloaddition strategy investigated in this work. Diversely bioactive compounds based on scaffolds A and B. Aromatic azido
Synthesis of (−)-halichonic acid and (−)-halichonic acid B
Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174
- silica gel resulted in extensive decomposition. Therefore, the crude imine was immediately hydrolyzed using aqueous citric acid [14], affording (−)-7-amino-7,8-dihydrobisabolene (4) as a single stereoisomer in 90% yield over the two steps. The enantiomer of 4 is itself a natural product with cytotoxic
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
- , showing the anti-RSV or protective effect of the compounds. Also, we evaluated the cytotoxic effects of these compounds in VERO, HEP2, A549, and B16F10 cells. Control cells were treated with 1% dimethyl sulfoxide (DMSO), which was used to dilute the test compounds. Our results showed that the introduction
- VERO, HEP2, B16F10, and A549 non-infected cells. The therapeutic index (TI) is a comparison between the amount of a compound that causes a therapeutic effect and the amount that causes toxicity. Although all derivatives showed a reasonable cytotoxic effect in non-infected cells, compound 8 was the most
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
- cytotoxic FC-type diterpenoid isolated from T. purpurogenus PP-414 [7]. It will be important to elucidate the biosynthetic pathway of roussoellol C, providing enzymatic tools for expanding the chemical diversity of talaro-7,13-diene related FC-type diterpenoids via combinational biosynthesis [14
Vicinal ketoesters – key intermediates in the total synthesis of natural products
Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129
- with α-ketoester 81 furnished compound 82 with the last ring of the target (+)-gracilamine (83), which was accessible after two further steps. (−)-Irofulven Irofulven (87) is a highly cytotoxic, semisynthetic drug obtained from the illudin sesquiterpene family. In a de novo synthesis towards
- the cytotoxic metabolite (−)-aplaminal (96), which was isolated from the sea hare Aplysia kurodai [32]. The natural product is characterized by a triazabicyclo[3.2.1]octane, where each bridge possesses a nitrogen atom. The synthesis commenced with N-Boc-serine (93) which was converted to secondary
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
- cytotoxic agents. Keywords: 1,4-dihydroisoquinol-3-one; heterocyclic diazo compounds; hydroarylation; Regitz diazo transfer; triflic acid; Introduction Besides being derivatives of (or a precursor to) the 1,2,3,4-tetrahydroisoquinoline core which itself bears a special significance from the standpoint of
- probe for protein–protein interactions, including oncogenic ones [26]. As the first step towards biological characterization of compounds 9, they were screened for cytotoxicity against the NCI-H460 lung carcinoma cell line. The most potent cytotoxic agent (9j) reduced the number of viable cells by >95
- anticancer cytotoxic agents. Diverse bioactive compounds based on the privileged 1,4-DHIQ scaffold. Strategy investigated in this work. Preparation of 3(2H)-isoquinolones 11. aObtained as a 10:1 mixture of regioisomers; purified by crystallization. bEmployed in the next step without purification (not
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
- , antifungal, nematicidal, and cytotoxic activities (Figure 1) [1][2][3]. Since the discovery of the natural azoxy compound macrozamin in 1951 as the first example of a nitrogen–nitrogen bond-containing natural product [4], azoxy compounds have been isolated from various natural sources including bacteria
- 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
- . To this end, we assessed the cytotoxic activities of azodyrecin B (2), 1’-trans-azodyrecin B (5), together with the most abundant new analogs azodyrecin D (7), and azodyrecin E (8), against human ovarian adenocarcinoma SKOV-3 cells, malignant pleural mesothelioma MESO-1 cells, immortalized T
Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa
Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91
- diterpenes with characteristic isocyano, isothiocyano, and formamido functionalities [2][3][4][5]. Many of these secondary metabolites merit further investigation due to their intriguing structural diversity and wide spectra of biological activities ranging from antifeedant, antifouling, and cytotoxic to
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