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Search for "cancer" in Full Text gives 493 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

  • Dmitry B. Vinogradov,
  • Alexei N. Izmest’ev,
  • Angelina N. Kravchenko,
  • Yuri A. Strelenko and
  • Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

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  • [16][17]. Recent studies of the antitumor activity of imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazines revealed a number of compounds with a high antiproliferative effect towards a large number of human cancer cell lines (Figure 1) [18][19]. Therefore, the synthesis of new imidazothiazolotriazines and
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Published 28 Jul 2023

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

  • Hong Zhou,
  • Xu-Yang Li,
  • Hong-Bin Fang,
  • He-Zhong Jiang and
  • Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

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  • from agarwood. Unfortunately, none of the new compounds exhibits biological activity against LPS-induced inflammation in Raw264.7 cells and human breast cancer cells. However, we have drawn good conclusions for SAR studies based on the current study and our previous study. These compounds will be
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Published 30 Jun 2023

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

  • Dileep Kumar Singh and
  • Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

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  • /instruments. Some of these synthesized N-substituted pyrrole derivatives were evaluated for in vitro cytotoxicity for various cancer cell lines. In 2014, Wang et al. [78] demonstrated a modified Clauson–Kaas reaction to synthesize various N-substituted pyrroles 53 in 75–95% yields by reacting various aromatic
  • –98% yields by reacting various amines 60 and 2,5-DMTHF 2 under solvent-free conditions in the presence of 5 mol % molecular iodine as catalyst (Scheme 29a). These synthesized products were tested against various cancer cells in vitro. In the proposed mechanism, deprotection of the methoxy group of
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Published 27 Jun 2023

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

  • Yuan-Nan Yuan,
  • Jin-Qiang Li,
  • Hong-Bin Fang,
  • Shao-Jun Xing,
  • Yong-Ming Yan and
  • Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

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  • methods. Selected compounds were evaluated for their biological properties against a mouse pancreatic cancer cell line and inhibitory effects on iNOS and COX-2 in RAW264.7 cells. Keywords: arthropod; iNOS; Kronopolites svenhedini (Verhoeff); non-peptide small molecules; Introduction The millipede (class
  • 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
  • DFT calculations at the B3LYP/6-311G(d,p) level of theory. The program SpecDis 1.62 was used to generate the CD spectra [31]. Biological evaluation Antitumor assay Panc02-h7-GP-GFP cells (derived from the transformation of mouse pancreatic cancer cell line Panc02-h7) were maintained at 37 °C in a 5
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Published 07 Jun 2023

Nucleophile-induced ring contraction in pyrrolo[2,1-c][1,4]benzothiazines: access to pyrrolo[2,1-b][1,3]benzothiazoles

  • Ekaterina A. Lystsova,
  • Maksim V. Dmitriev,
  • Andrey N. Maslivets and
  • Ekaterina E. Khramtsova

Beilstein J. Org. Chem. 2023, 19, 646–657, doi:10.3762/bjoc.19.46

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  • targeted cancer therapy development. Keywords: 1,4-benzothiazine; 1,3-benzothiazole; 1H-pyrrole-2,3-diones; nitrogen heterocycle; sulfur heterocycle; Introduction Pyrrolo[2,1-b][1,3]benzothiazole (PBTA) is an angularly fused sulfur and nitrogen-containing heterocyclic scaffold. Its derivatives are
  • popular in medicinal chemistry and pharmacology as potential biologically active compounds. In particular, PBTAs were found to be promising inhibitors of centromere-associated protein E (CENP-E) (Figure 1), which is demanded for the development of targeted cancer therapy [1]. Furthermore, candidate
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Published 11 May 2023

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

  • Nan Yang,
  • Yi-Yan Zhu,
  • Wei-Xiu Lin,
  • Yi-Long Lu and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

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  • stimulus-responsive supramolecular vesicles and molecule-scale drug carriers are considered to have potential for cancer drug delivery. However, such supramolecular systems are not suitable for oral administration, which is a convenient and patient-preferred method of drug delivery, especially for patients
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Published 08 May 2023

Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C

  • Karolina Wątroba,
  • Małgorzata Pawełczak and
  • Marcin Kaźmierczak

Beilstein J. Org. Chem. 2023, 19, 434–439, doi:10.3762/bjoc.19.33

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  • ]. Cathepsin C is an emerging pharmacological target due to its involvement in inflammatory and autoimmune diseases. Cathepsin C is upregulated in immune-related cells. DPPI also plays a role in the development of cancer – particularly in the liver and breast, hence the potential contribution of its inhibitors
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Published 12 Apr 2023

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

  • Jorge de Lima Neto and
  • Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

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  • functional groups to obtain the desired compounds and especially with regard to the structure–activity relationship of these molecules against different types of cancer cells (see Section 3). Harras and co-workers [57] achieved the total synthesis of combretastatins D-2 (2) and D-4 (4) and the formal
  • these compounds in folk medicine for the treatment of different types of diseases, such as inflammatory processes, viral infections, metabolic disorders and some types of cancer [13][14][15][16][17][18][19]. The first biological studies of the combretastatin D series exploited their anticancer activity
  • , since Pettit and co-workers, in a program from U.S. National Cancer Institute for the discovery of new anticancer agents, initially showed that combretastatins D-1 (1) and D-2 (2) isolated from the bark of the Combretum caffrum tree inhibited the growth of the murine lymphocytic leukemia cell line P388
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Published 29 Mar 2023

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

  • Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

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  • MeI in DMF to afford the cationic products 85 and 87 in good yields. The synthesized conjugates exhibited high photocytotoxicity towards A549 cancer cells as compared to a tumor-localizing and potent photosensitizing agent, TMPyP. Further, the authors discovered that the porphyrin-carboline conjugates
  • -soluble nanowires, nanorods, and nanospheres. In addition, these triazoloporphyrins have a wide range of medical applications, including photoinduced cytotoxicity against cancer cells, drug delivery, as phototherapeutic agents, and PDT applications. I believe this review will be useful and encourage
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Published 22 Mar 2023

Synthesis, α-mannosidase inhibition studies and molecular modeling of 1,4-imino-ᴅ-lyxitols and their C-5-altered N-arylalkyl derivatives

  • Martin Kalník,
  • Sergej Šesták,
  • Juraj Kóňa,
  • Maroš Bella and
  • Monika Poláková

Beilstein J. Org. Chem. 2023, 19, 282–293, doi:10.3762/bjoc.19.24

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  • that are involved in diseases such as viral infections, diabetes or cancer and lysosomal storage disorders [7][8][9]. Thus, iminosugar derivatives are promising candidates for pharmaceuticals, and many of them have already been approved for treatments, for example miglitol (type 2 diabetes), miglustat
  • found to suppress metastasis, the potentially positive effect of swainsonine on cancer patients is strongly reduced by its severe side effects [15][16]. These are associated with the accumulation of oligomannoside structures in tissues, serum, and urine, which is caused by the co-inhibition of lysosomal
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Published 06 Mar 2023

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

  • Cécile Alleman,
  • Charlène Gadais,
  • Laurent Legentil and
  • François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

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  • 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
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Published 03 Mar 2023

An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

  • Tharun K. Kotammagari,
  • Sweta Misra,
  • Sayantan Paul,
  • Sunita Kunte,
  • Rajesh G. Gonnade,
  • Manas K. Santra and
  • Asish K. Bhattacharya

Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19

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  • , 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
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Published 21 Feb 2023

Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2E,4E)-dienones

  • Benedikt Kolb,
  • Daniela Silva dos Santos,
  • Sanja Krause,
  • Anna Zens and
  • Sabine Laschat

Beilstein J. Org. Chem. 2023, 19, 176–185, doi:10.3762/bjoc.19.17

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  • 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
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Published 17 Feb 2023

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

  • Sedat Ünal,
  • Gamze Varan,
  • Juan M. Benito,
  • Yeşim Aktaş and
  • Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

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  • , 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
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Published 13 Feb 2023

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

  • Christian Schumacher,
  • Jas S. Ward,
  • Kari Rissanen,
  • Carsten Bolm and
  • Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

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  • 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
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Published 27 Jan 2023

Preparation of β-cyclodextrin/polysaccharide foams using saponin

  • Max Petitjean and
  • José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

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  • 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
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Published 24 Jan 2023

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

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  • 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
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Published 02 Jan 2023

A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition

  • Anastasia Vepreva,
  • Alexander Yanovich,
  • Dmitry Dar’in,
  • Grigory Kantin,
  • Alexander Bunev and
  • Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1649–1655, doi:10.3762/bjoc.18.177

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  • 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
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Published 06 Dec 2022

A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

  • Ksenia Malkova,
  • Andrey Bubyrev,
  • Vasilisa Krivovicheva,
  • Dmitry Dar’in,
  • Alexander Bunev and
  • Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

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  • 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
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Published 02 Dec 2022

One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

  • Juan Lu,
  • Bin Yao,
  • Desheng Zhan,
  • Zhuo Sun,
  • Yun Ji and
  • Xiaofeng Zhang

Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171

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  • 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
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Published 28 Nov 2022

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

  • Sasha Hayes,
  • Aya C. Taki,
  • Kah Yean Lum,
  • Joseph J. Byrne,
  • Merrick G. Ekins,
  • Robin B. Gasser and
  • Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

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  • , 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
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Published 15 Nov 2022

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

  • Jia-Hua Huang,
  • Jian-Ming Lv,
  • Liang-Yan Xiao,
  • Qian Xu,
  • Fu-Long Lin,
  • Gao-Qian Wang,
  • Guo-Dong Chen,
  • Sheng-Ying Qin,
  • Dan Hu and
  • Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

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  • 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
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Published 05 Oct 2022

On drug discovery against infectious diseases and academic medicinal chemistry contributions

  • Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

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Published 29 Sep 2022

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

  • Neda Rafieiolhosseini,
  • Matthias Killa,
  • Thorben Neumann,
  • Niklas Tötsch,
  • Jean-Noël Grad,
  • Alexander Höing,
  • Thies Dirksmeyer,
  • Jochen Niemeyer,
  • Christian Ottmann,
  • Shirley K. Knauer,
  • Michael Giese,
  • Jens Voskuhl and
  • Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

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  • 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
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Published 23 Sep 2022

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

  • Nguyen Tran Nguyen,
  • Vo Viet Dai,
  • Nguyen Ngoc Tri,
  • Luc Van Meervelt,
  • Nguyen Tien Trung and
  • Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

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  • 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
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Published 31 Aug 2022
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