Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• most common applications being the treatment of breast cancer. Studies have shown that breast cancer is tied to the ratio of 16α-hydroxyestrone (16αOHE1) and 2-hydroxyestrone (2OHE1), which are products of the metabolism of the estrogen 17β-estradiol. BIMs can shift the process of estrogen metabolism

• towards the production of 2OHE1, thus reducing the risk for estrogen-sensitive cancers, especially in combination with tamoxifen, which is an estrogen receptor modulator used in the treatment of breast cancer [4]. BIMs increase the efficacy of the antitumor activity of tamoxifen and reduce the side

• -effects that it can cause in the more sensitive subgroups of patients. Specifically, when DIM was used in tandem with tamoxifen, the ratio between 2OHE1/16αOHE1 increased up to 229%, as well as the concentration of the sex hormone binding globulin (SHBG) that inhibits the growth of breast cancer cells [4

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• that now produces more accurate quantification of lipids with a distinction of neutral EL and phosphoglycero ELs produced contradictory data. Indeed, a recent study that focused on ether glycerophospholipids (alkyl and alkenyl ether lipids) indicates that in breast cancer cells (average of 9 breast

• Parkinson disease [18], breast cancer [19] and in rectal adenocarcinoma [20] (in the last case by measuring lysophosphatidylcholine plasmalogen). Low levels of ether lipids are reported in inherited peroxisomal disorders (e.g., rhizomelic chondrodysplasia punctata or Zellweger syndrome) [21]. The severity

• constitutive Ca2+ entry thus influencing breast cancer cell migration [106]. 1.4 Analogues of PAF with modification at the sn-3 position Finally, a series of PAF’s analogues were reported by changing the structure of the phosphocholine polar head group. Ohno et al. replaced the trimethylammonium moiety by

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• (L929) (IC50 = 15.2 µM), breast cancer cells (MCF-7) (17.6 µM), and prostate cancer cells (PC-3) (18.9 µM). Discussion The introduction of a hydroxy group at C-2 rendered forpinioside C (2) inactive in antimicrobial assays compared to forpinioside B (1), however; both compounds were not active in the

• used in determining the cytotoxicity (IC50) of the isolated compounds as previously established [38][39]. The mammalian cell lines (mouse fibroblasts L929, adenocarcinomic human alveolar basal epithelial cells A549, HeLa cells KB-3-1, breast cancer cells MCF-7, epidermoid carcinoma cells (A431), and

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

• 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

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

• with a median effective dose values (ED50) of 3.3 and 5.2 μg·mL−1 (10.56 and 17.55 μM), respectively [16][17]. Vongvanich and co-workers performed a cytotoxicity assay of combretastatins D-3 (3) and D-4 (4) against human breast cancer cells (BC-1), human epidermoid carcinoma of the mouth (KB), a small

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

• 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

• -rengyolone (3) by using KHMDS as a base. The antiproliferative activity of these compounds was tested using MTT assays and the results revealed that these compounds are less efficient in inhibiting the growth of breast cancer cells. Structures of (±)-incarvilleatone (1), (±)-incarviditone (2), and

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

• also had better release, physical stability, and cytotoxicity [13]. CPT is an anticancer small molecule drug that inhibits the topoisomerase I enzyme, which has a critical role in cellular DNA functions [14], and is effective in a wide spectrum of cancers such as metastatic colon cancer, breast cancer

• -C6 nanoparticle formulation decreased upon incubation. Based on previous studies with breast cancer cell lines, it is comprehensible that anionic nanoparticles induce cell proliferation inhibition earlier than polycationic nanoparticles. The impact of anionic nanoparticles on free cholesterol level

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

• 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

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

• Dušan Đ. Škorić,
• Olivera R. Klisurić,
• Dimitar S. Jakimov,
• Marija N. Sakač and
• János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

• 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

• compound 3 against MDA-MB-231 and HeLa cell lines. B) Cytotoxicity of compounds 7, 23, and 24 on breast cancer cell line MDA-MB-231. Synthesis of 12-oxo intermediates. Reagents and conditions: a) EtOAc, pTsOH, reflux, 14 h (81%); b) K2Cr2O7, H3O+, H2O/Et2O, rt, 3 h (76% for 3; 71% for 7); c) SeO2, acetic

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• the doxorubicin-loaded cryogels, suggesting delivery of the drug was successful. These cryogels were also injected into mice, adjacent to an orthotopic breast cancer tumour, impeding tumour growth and metastasis. Several groups have reported on the use of composite cryogels for drug delivery, whereby

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• breast cancer cells by arresting the cell cycle and promoting apoptosis while showing no cytotoxicity against RAW 264.7 cells, thus demonstrating their selectivity [65][67]. Further, fumigaclavine was shown to exhibit antibacterial properties and to contribute to virulence in the model insect Galleria

• [72]. It was further shown to be cytotoxic and inhibiting cell cycle progression at G2/M phase [163]. Fumitremorgin C was shown to effect mammalian cells and inhibit the breast cancer resistance protein which imparts multidrug resistance and thus resistance to chemotherapeutics in breast cancer

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• relate cell-signaling pathways to TFs and cellular glycosylation state. Whereas analysis results are presented for all 29 cancer types, specific focus is placed on human luminal and basal breast cancer disease progression. Overall, the article presents a computational approach to describe TF–glycogene

• processes and specific glycosylation pathways. TF–pathway relationships in breast cancer We provide a more detailed description of our findings in breast cancer as an example. This disorder appears in 5 unique molecular subtypes based on the PAM50 classification [17]. These include the following: i) normal

• mechanisms that may contribute to different glycan signatures. In our analysis, TF–glycogene relationships for breast cancer derived by filtering Cistrome Cancer DB were enriched for the glycosylation pathways. Figure 3 summarizes these cancer-related TF–glycosylation pathway relationships for luminal (type

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• with a standard drug, doxorubicin, were screened for their cytotoxicity against various cancer lines (Figure 5, Table 3 and Figure S2, in Supporting Information File 1) such as MCF-7 (breast cancer), HeLa (cervical cancer), HEK293 (human embryonic kidney cells), A431 (skin cancer), A549 (lung cancer

• , 3ca, 3ga in the breast cancer cell line, MCF7 and (B) doxorubicin against the panel of tested cancer cell lines. Dose–response curve of γ-carbolines 3ac, 3bc, 3ca, 3ga in macrophage cell line, RAW264.7. Laser scanning confocal microscopy studies (λex = 405 nm; collection range = 420–470 nm) for uptake

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• pancreatic carcinoma and triple-negative breast cancer (Scheme 23B) [55]. Konteatis et al. adopted a similar approach by using the direct fusion for the preparation of bisdifluorocyclic biguanides as IDH1/2 inhibitor intermediates (Scheme 23C) [56]. However, sodium dicyanamide has been mainly used as an

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• their LNP formulation to functionalize LNPs with an aptamer specific for the human epidermal growth factor 2 (HER2) receptor. Therein, functionalized LNPs increased siRNA delivery and subsequent sensitivity of the doxorubicin-resistant HER2-positive breast cancer cell lines by ≈2-fold over LNPs with no

Simulating the enzymes of ganglioside biosynthesis with Glycologue

• Andrew G. McDonald and
• Gavin P. Davey

Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

• disorders of ganglioside biosynthesis can lead to a number of neuropathies, including motor deficits, microcephaly, sensory loss, and autistic features [10][11]. Certain gangliosides, such as GM2, have been identified as tumor markers for breast cancer stem cells [12], while members of the alpha-series

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• production [11] that plays an important role in the growth of various cancerous tissues (colon, lung, and breast cancer) and as antagonists of the human A3 adenosine receptor [12]. Aminophthalazines have been also evaluated for their inhibitory activity toward phosphodiesterases such as PDE-5 (Figure 1) [13

The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

• Deniz Tözendemir and
• Cihangir Tanyeli

Beilstein J. Org. Chem. 2021, 17, 494–503, doi:10.3762/bjoc.17.43

• a low (1 mol %) catalyst loading, to obtain enantiomerically enriched β-naphthyl-β-sulfanyl ketones with up to 96% ee. The target adducts are the core structure of seco-raloxifene derivatives, which are potent anti-breast cancer agents [32]. In addition, the same scaffold has also shown urease

• , which have potent activity against breast cancer. The easy access to the corresponding sulfones presents a versatile route for the implementation of a new biologically active moiety, the sulfone, to the β-naphthyl-β-sulfanyl ketones. The enantioenriched products of both classes can be evaluated as

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• presence of DNA, and another intrinsically disordered binding partner, breast cancer antigen 1 (BRCA1) (Figure 12). In this work the strategy employed involved the introduction of a perfluorinated [19F]3,5‐bis(trifluoromethyl)benzyl-based tag into the single cysteine residue of Myc. This modification

Comparative ligand structural analytics illustrated on variably glycosylated MUC1 antigen–antibody binding

• Christopher B. Barnett,
• Tharindu Senapathi and
• Kevin J. Naidoo

Beilstein J. Org. Chem. 2020, 16, 2540–2550, doi:10.3762/bjoc.16.206

• epithelial cells, the mixture of O-glycans that glycosylate mucins are extended core 2 structures, while in breast cancer cells, O-glycan mass decreases (hypoglycosylation), and there is an increase in abundance of sialylated core 1 [15]. The upregulation of Tn (αGalNAc) and STn (αNeuAc-2,6-αGalNAc) antigens

• breast cancer [11][13]. We use MD simulations to investigate the conformational behavior of (glyco)peptide antigens bound to the AR20.5 antibody and to investigate the hypothesis that the glycan modulates the conformation of the peptide portion of the antigen. Primarily showcasing a structural analytics

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

• Aleksandar Pashev,
• Nikola Burdzhiev and
• Elena Stanoeva

Beilstein J. Org. Chem. 2020, 16, 1456–1464, doi:10.3762/bjoc.16.121

• heterocycle is present in several alkaloids such as emetine (1) and related compounds, that exhibit biological activities such as glucosidase inhibition, anti-amoebic properties as well as activity against breast cancer cell lines [2]. Notable examples of synthetic compounds include the dipeptidyl peptidase

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

• Renata Kaczmarek,
• Dariusz Korczyński,
• James R. Green and
• Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

• hexacarbonyls with 2'-deoxyuridines revealed pronounced in vitro activity against MCF-7 and MDA-MB-231 human breast cancer cells [32][33]. A recent investigation of hexacarbonyl dicobalt adducts of nucleosides containing derivatives of propargyl alcohol demonstrated their antiproliferative activities for the

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

• Shital K. Chattopadhyay,
• Subhankar Ghosh,
• Sarita Sarkar and
• Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

• three steps. Biological studies Although approved for the treatment of CTCL, SAHA has been shown to display anticancer activity over a large range of other hematological and solid malignancies such as leukemia [24], lung cancer [25], cervical cancer (HeLa), breast cancer (MCF-7) [26], mesothelioma [27

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• shown in Figure 11 was tested in vitro on human breast cancer cells MCF-7. One-photon absorption induced fluorescence demonstrated that this dendrimer is efficiently internalized after 3 h of incubation, more after 24 h, and was non-toxic at 50 μg mL−1 without irradiation. Two-photon irradiation was