Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• compared to the stereoisomers 75, with enhanced activity observed upon substitution of the aromatic ring. Interestingly, hydrolysis of the acetate group on C-3 did not significantly affect the antiproliferative effect, indicating that the activity is primarily influenced by the stereochemistry and

• 17β-HSD5 in transfected HEK-293 cells (91–92% at 3 µM). The monomethylated lactone 117 showed better activity (73% at 0.3 µM) than the dimethylated compound 116 (54% at 0.3 µM). However, no inhibition was observed for 17β-HSD3. Interestingly, the compounds also demonstrated an antiproliferative effect

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

• [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

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

• anticancer efficiency of CPT-loaded nanoparticles on 2D cell cultures According to the results of the conventional 2D cell culture study, the CPT-loaded poly-β-CD-C6 nanoparticle treatment group in CT26 cells had the highest antiproliferative effect after 48 h (Figure 5a). When compared to CPT solution

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

• Lukáš Ďurina,
• Anna Ďurinová,
• František Trejtnar,
• Ľuboš Janotka,
• Lucia Messingerová,
• Jana Doháňošová,
• Ján Moncol and
• Róbert Fischer

Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188

• hydrogen peroxide catalyzed by phosphotungstic heteropoly acid. Each of the key reactions proceeded with an excellent diastereoselectivity (dr > 95:5). (±)-Codonopsinol B was prepared in 10 steps with overall 8.4% yield. The antiproliferative effect of (±)-codonopsinol B and its N-nor-methyl analogue was

• evaluated using several cell line models. Keywords: alkaloids; antiproliferative effect; codonopsinol B; diastereoselectivity; pyrrolidines; Introduction Codonopsinol B (1) is a polyhydroxylated pyrrolidine alkaloid isolated from the roots of the plant Codonopsis pilosula (Figure 1) [1]. This compound was

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

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• antiproliferative effect from this and a previous investigation (N-methylcoclaurine (1)) have in common a 4-hydroxybenzyl residue at C-1. These results indicate that the „aromatic decoration“ of benzylisoquinolines (phenoxy or benzyloxy residues on both aromatic rings) [15] is also important for antiproliferative

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• synthetic derivatives have been reported to exert an antiproliferative effect in different types of tumors related (e.g., breast, endometrial cancer [5]) and unrelated (e.g., melanoma, colon carcinoma [6][7]) to reproductive organs. Considering these aspects, the GnRH could serve as a targeting unit with

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• . Small peptides that recognize target receptors on tumor cells might be suitable targeting moieties for this purpose. Hormone peptides, in particular, GnRH and somatostatin derivatives that possess antiproliferative effect on their own, are among the best candidates as homing peptides [10]. A.V. Schally

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• . Another natural isoform of GnRH is GnRH-III (pGlu-His-Trp-Ser-His-Asp-Trp-Lys-Pro-Gly-NH2), which has been isolated from sea lamprey. GnRH-III binds to GnRH-R overexpressed on the cancer cell surface, resulting in an antiproliferative effect but seems to be less potent than the rest GnRH analogs regarding

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

• Salvatore V. Giofrè,
• Santa Cirmi,
• Raffaella Mancuso,
• Francesco Nicolò,
• Giuseppe Lanza,
• Laura Legnani,
• Agata Campisi,
• Maria A. Chiacchio,
• Michele Navarra,
• Bartolo Gabriele and
• Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

• have been performed using 6e as model compound. In general, all the synthesized compounds showed a certain degree of antiproliferative effect against all the examined cancer cells with a similar trend (see Supporting Information File 1, Figure S1). Noteworthy, compound 6e exhibited superior activity

• < 0.01 vs control) and 48 (P < 0.001 vs control). Lesser, but still significant, an antiproliferative effect was also found treating the cells with 6e at concentrations of 50, 10 and 5 µM for all time of exposure, while a concentration of 1 µM did not exert a significant antiproliferative effect

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• amastigotes with an IC50 value of 100 μg/mL. Except for compound 1 that exhibited a weak antileishmanial activity at 50 μM (20%) against L. amazonensis intracellular amastigotes, none of the other sesquiterpenes displayed antiparasitic activity. Compounds 1–3 showed less than 50% antiproliferative effect on

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

• Roberto Romeo,
• Caterina Carnovale,
• Salvatore V. Giofrè,
• Maria A. Chiacchio,
• Adriana Garozzo,
• Emanuele Amata,
• Giovanni Romeo and
• Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

• 4.50–5.10 and 4.25–4.75 ppm, respectively in 13 and 14, as a doublet of doublets, for the methylene group at C-4’ position. Biological tests The antiproliferative effect of the obtained derivatives was tested on a panel of cell lines: african green monkey kidney cells (Vero and BS-C-1), human

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• , which were subsequently demethylated using BBr3 to give compounds 47–51 in 48 to 78% yield. Compound 47 (R1 = H, R2 = OH, R3 = OH) showed antiproliferative activity with an IC50 of 0.88 ± 0.08 µM in vitro. Compound 38 (alkyl = CH(CH3)CH2CH3) exhibited a moderate antiproliferative effect (IC50 = 11.0 ± 1

Colchitaxel, a coupled compound made from microtubule inhibitors colchicine and paclitaxel

• Karunananda Bombuwala,
• Thomas Kinstle,
• Vladimir Popik,
• Sonal O. Uppal,
• James B. Olesen,
• Jose Viña and
• Carol A. Heckman

Beilstein J. Org. Chem. 2006, 2, No. 13, doi:10.1186/1860-5397-2-13

• combination had antagonistic effects. Other researchers found that the antiproliferative effect of paclitaxel was relatively little affected by the presence of microtubule depolymerizing agent, N-acetylcolchinol [50]. Workers who studied cells cultured in vitro found high IC50 levels, in the 10–50 nM range