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Search for "cancer" in Full Text gives 493 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
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
Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues
Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10
- acetylation; Introduction In the last few decades, modification of nucleoside/nucleotide analogues has been a field of keen interest to researchers due to their therapeutic properties for treatment of cancer, viral and microbial infections [1][2][3][4][5][6][7][8][9]. The very first cytotoxic
- chemotherapeutic agents used for the treatment of cancer were nucleoside analogues and nucleobases [10]. Azidothymidine (1, AZT) was the first approved drug for the treatment of human immunodeficiency virus (HIV) [11][12]. Subsequently, a large number of sugar modified nucleosides, such as ddC (zalcitabine) [13
1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis
Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5
- -workers synthesized other naphthoquinone derivatives 37 from β-NQSNa (18) [86]. These compounds were evaluated for their antiproliferative activities on human cancer cells, with three of them being the most active (37a–c). It has been shown that the mechanism of action passes through the production of
- human cancer cell lines, including leukemia (HL-60), melanoma (MDA-MB-435), colon cancer (HCT-116), and central nervous system cancer (SF-295). 4-Amino-1,2-naphthoquinones 43a–c exhibited considerable cytotoxic activities, with 43a being the most active against HL-60 and MDA-MB-435 cells (Scheme 12
Peptide stapling by late-stage Suzuki–Miyaura cross-coupling
Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1
- + 7 for two helix turns, respectively, followed by Ru-catalysed cross-linking [7]. By this robust and reliable approach, a library of stapled peptides was generated influencing diverse α-helical dominated protein–protein interactions (PPI) spanning pathways involved in cancer, infectious diseases
- part in the destruction complex for β-catenin labelling in the canonical Wnt signalling. Loss-of-function mutations in this pathway lead to a dysregulated signal transduction causing cancer [75][76]. All-hydrocarbon stapled peptides comprising amino acids 467 to 481 of the axin CBD had been studied in
Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193
- letrozole [5] and entrectinib [6], with especially entrectinib showing a potent anticancer activity against a broad spectrum of human cancer cell lines. In recent decades, the construction of a hybrid system with varied biological and pharmaceutical activities has received extensive attention from medicinal
Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation
Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188
- . tangshen). This crude drug is called Dangshen in Chinese and Tojin in Japanese and has been used as traditional Chinese medicine with numerous beneficial pharmacological activities to treat multiple diseases [8][9], including cancer [10][11][12][13]. It is assumed that polyacetylenes, phenylpropanoids
- human cancer cell lines has never been described. In view of this, we have developed an efficient and highly diastereoselective approach towards codonopsinol B (1) and its N-nor-methyl analogue 2 from achiral starting materials and evaluated their anticancer activity using four different cancer cell
- cancer cell lines [14]. For this reason, the compounds 1 and 2 were prepared first in their racemic form to begin the initial biological studies. Results and Discussion The starting isoxazolidine-4,5-diol 3, possessing the desired 3,4-trans configuration (Scheme 1), will be prepared by using our
GlycoBioinformatics
Beilstein J. Org. Chem. 2021, 17, 2726–2728, doi:10.3762/bjoc.17.184
- transcription factors using next-generation sequencing expression data of glycoenzymes in cancer cell lines. The latter paper uses knowledge from current open access glycomic databases to curate and validate glycan structures reported on proteins in the Protein Data Bank (PDB) database. Overall, the wide
The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids
Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183
- data on structure–activity relationship are still rare. First, we assessed the antiproliferative activity of the benzylisoquinolines 2a–f, 3a–c and 4 by CellTiter Blue cell viability assay and used tetrandrine as reference compound. In the cervical cancer cell line HeLa, none of the newly tested
- compounds showed antiproliferative effects, in contrast to tetrandrine which potently inhibits cancer cell proliferation. In the multidrug resistant leukemia cell line VCR-R CEM proliferation was measurably reduced upon treatment with two of the investigated compounds, rac-armepavine (2a) and rac
- . Interestingly, macrocyclic bisbenzylisoquinolines such as tetrandrine [48][49] and related alkaloids [50], have been reported to inhibit P‐glycoprotein (P-gp), a crucial factor of multidrug resistance in cancer. This is noteworthy as multidrug resistance is still a major problem in cancer therapy and no
Synthetic strategies toward 1,3-oxathiolane nucleoside analogues
Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182
- ][4]. These compounds are the structural analogues of the naturally occurring 2’-deoxynucleosides, the building blocks of DNA. The World Health Organization (WHO) newsroom announced the primary statistics that HIV and cancer remain a significant global public health issue, having claimed over 47.6
- million lives so far [5][6]. The statistics confirm that 1 in 6 deaths happening globally are due to cancer [5]. In 2019, 690,000 people died from HIV-related causes worldwide and by the end of 2019, around 38 million people were living with HIV. From these, 1.7 million people were newly diagnosed [6
- ]. Nucleoside analogues have been in clinical use for almost 50 years and have been the mainstay of treating patients with cancer and viral infections [7][8]. The 2’,3’-dideoxynucleoside analogues, such as AZT (zidovudine), ddI (didanosine), ddC (zalcitabine), and d4T (stavudine), are modified examples of the
Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction
Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174
- and metabolic stability of the molecule [16]. Steroid molecules with nitrogen-containing heterocyclic rings are promising candidates for the treatment of many types of cancer or hormonal disorders [17]. There are several examples of steroidal tetrazoles showing anticancer potential (Figure 1) [18][19
- six human tumor cell lines (MCF-7 estrogen receptor positive breast adenocarcinoma, MDA-MB-231 estrogen receptor negative breast adenocarcinoma, PC-3 prostate cancer, HeLa cervix carcinoma, HT-29 colon adenocarcinoma, and A549 adenocarcinomic human alveolar basal epithelial cells). Standard MTT assay
- activity toward the HeLa cell line (IC50 = 6.97 μM), while tetrazole 22 showed strong and selective activity toward the HT-29 cell line (IC50 = 6.06 µM). Compounds 7, 23, and 24, which showed strong cytotoxicity to the breast cancer cell line MDA-MB-231 (in addition to compound 3), also exhibited a
α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions
Beilstein J. Org. Chem. 2021, 17, 2570–2584, doi:10.3762/bjoc.17.172
- reduction in conjugation. Another example of a tandem α-ketol rearrangement was used in the total synthesis of delitschiapyrone A (49), a cytotoxic natural product with previously demonstrated efficacy against several cancer cell lines. The final steps of the synthesis include a Diels–Alder reaction between
Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing
Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171
- highlights the fundamentals of macroporous cryogel preparation, cryogel properties that can be useful in the highlighted biomedical applications, followed by a comprehensive review of recent studies in these areas. Research evaluated includes the use of cryogels to combat various types of cancer, for
- pore size range was between 50–300 μm, and small concentrations of laponite found in the gel wall helped with sustained release of a number of proteins with diverse properties [37]. Injectable nanocomposite cryogels have also appeared in research as a method to combat cancer. Bauleth-Ramos et al. used
- accumulating drug payloads into the tumour. Further testing was said to be targeted towards the use of the cryogel as an approach to delay or prevent cancer recurrence through the induction of in situ cancer vaccination mediated by antigens and danger signals released from the apoptotic cancer cells [82
Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives
Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163
- in many natural products, pharmaceuticals, and bioactive molecules. For instance, some pyridine derivatives have been used for therapy of HIV, cancer, inflammation, microbial infection and so on [1][2][3][4][5]. In addition, it is also an important synthetic unit, which is frequently used as catalyst
- % yield) and monodesulfonated nicotinate 17 (in 70% yield), respectively (Scheme 6). Selenyl- and sulfenylpyridine derivatives are gaining prominence due to the prospective biological activities. They could be used for treatment of HIV, cancer, inflammation, and microbial infection. Therefore, the
Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines
Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162
- [44][45]. In particular, they have been widely explored for the treatment of Alzheimer's disease [46][47][48][49][50][51], human cancer [52][53], and tuberculosis [54] (Figure 1). Taking into consideration the significant medicinal potential of tetrahydroacridines and the lack of knowledge concerning
Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions
Beilstein J. Org. Chem. 2021, 17, 2417–2424, doi:10.3762/bjoc.17.158
- against cancer [6][7], tuberculosis [8], Gram-positive bacteria [9], and they are used in treatment of epilepsy [10] and Alzheimer disease [11][12][13]. The synthesis of compounds of the 1,2,4-oxadiazole series is an actual task in organic and medicinal chemistry (see selected reviews on this topic [14
Strategies for the synthesis of brevipolides
Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157
- human cancer cell lines and inhibition of the chemokine receptor CCR5, make them attractive synthetic targets. This review article highlights the recent synthetic methodologies and briefly summarizes their biological activities. Keywords: brevipolides; 5,6-dihydro-α-pyrone; Furukawa-modified Simmons
- has long been used in folk medicines to treat headaches (Panama) and diarrhea (Paraguay) [6], for protection after giving birth (Panama, Indonesia, Malaysia) [6][7][8][9], against worms for newborn infants (Indonesia) [6], for prevention and treatment of different types of cancer (Indonesia) [10
- , C5’S, and C6’S. Most brevipolide members exhibited cytotoxicity against various targets, including human colon, breast, laryngeal, cervix, prostate, and nasopharyngeal cancer cell lines with ED50 and IC50 values ranged in micromolar order [1][4][12]. One member showed activity in an enzyme-based
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