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

• -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

• reduced the IC50 value. It is believed that chitosan's antiproliferative properties also are involved in this situation. When cell viability in HT29 cells was evaluated, it was observed that the polycationic derivative had the lowest IC50 value. It can be said that the chitosan coating did not cause a

• 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

• ]. In both traditional and 3D cell culture investigations, incubating cells with empty CD nanoparticles and drug solutions has a synergistic impact due to the antiproliferative activity of the CD nanoparticles themselves. Co-administration of pharmaceuticals with empty nanoparticles, as well as

Vicinal ketoesters – key intermediates in the total synthesis of natural products

• Marc Paul Beller and
• Ulrich Koert

Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129

• pentacyclic, antiproliferative quinoline alkaloid camptothecin (65), Peters et al. used an α-ketoester moiety in an auxiliary controlled approach towards the only stereogenic center present in the natural product (Scheme 10) [25]. First, the ketoacid 60 was esterified with 8-phenylmenthol (61) to yield the α

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

• Mio Matsumura,
• Kaho Tsukada,
• Kiwa Sugimoto,
• Yuki Murata and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

• -alkynylselenides III exhibits a binding interaction between calf-thymus DNA and human serum albumin [13]. Moreover, imidazopyridine derivatives IV with selanyl groups, 3-aryl- or alkylselanylimidazo[1,2-a]pyridines, were reported to act as potential antioxidants and showed antiproliferative activity [14][15

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• biological activities such as anti-COVID-19 [5], anticancer [6][7][8], antibacterial activity against Staphylococcus aureus and Bacillus subtilis [9][10], antifungal agents against Candida albicans and phytopathogenic fungi [11][12], and antiproliferative against different cell lines (e.g., PC3, HCT-116, and

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

• Long Zhao,
• Mao-Lin Yang,
• Min Liu and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

• biological activities, including anticancer [9], neuroprotective [10], antiproliferative and antifungal activities [11]. Due to the significant bioactive properties of the 3,4-dihydroquinazoline and 4H-3,1-benzothiazine moieties, many preparation procedures have appeared in the literature for the synthesis

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

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

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

• Rodolfo H. V. Nishimura,
• Thiago dos Santos,
• Valter E. Murie,
• Luciana C. Furtado,
• Leticia V. Costa-Lotufo and
• Giuliano C. Clososki

Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206

• -, meta-, and para-substituted N-methylanilines as well as substituted anilines and furnished the corresponding 4-anilinoquinazolines in good yields. Preliminary screening of the synthesized compounds against tumor cells (HCT-116 and T98G) showed promising antiproliferative properties. Keywords: 4

• at C6 as substituents in quinazoline ring has been related to increased antiproliferative action of this class of compounds [28]. Therefore, we wish to report the preparation of a library of novel quinazoline-based antitumor candidates through reaction of 4-chloro-6-halo-2-phenylquinazolines with

• being a more environmentally friendly methodology. To evaluate the antiproliferative properties of the 4-anilinoquinazolines we obtained in this study, we screened the synthesized compounds against a set of tumor cell lines including HCT-116 (human colorectal carcinoma), MCF-7 (human breast

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

• lines U87-MG, HepG2, JEG-3 and MOLM-13 (AML cell line) as well as immortalized proximal tubular cells HK2. We have very recently found out that even enantiomerically pure polyhydroxylated pyrrolizidine alkaloids with proven antiglycosidase activities may not exhibit antiproliferative effects against

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

• relationships in this chemotype. Keywords: acyl Pictet–Spengler reaction; alkaloids; antiproliferative activity; benzyltetrahydroisoquinolines; ion channels; protective group; total synthesis; Introduction The benzylisoquinoline alkaloids are a large and diverse class of plant secondary metabolites including

• , antitumor, and antiviral effects [15]. Mechanistically, they have been shown to block two pore channel 2 (TPC2), an endolysosomal cation channel which is important for cellular migration and survival [6][15][46][47]. In our recent search for TPC2 blockers with antiproliferative potential we identified ring

• ” retained antiproliferative activity, while losing activity on TPC2 [15]. This prompted us to analyze both TPC2 modulating and antiproliferative activities of the alkaloids from this project. TPC2 modulation To assess the activity of racemic 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids on TPC2 in

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

• different ketone and enone precursors from cholic acid, deoxycholic acid, and chenodeoxycholic acid was established. Newly obtained tetrazole derivatives were characterized by NMR and X-ray diffraction spectroscopy. In a number of cases, preliminary antiproliferative tests of new compounds showed strong and

• selective activity towards certain tumor cell lines. Keywords: antiproliferative activity; Schmidt reaction; steroids; tetrazoles; trimethylsilyl azide; Introduction Bile acids are naturally occurring steroidal surfactants that play various biological roles. Besides the well-known role as lipid

• obtained in this way were subjected to antiproliferative activity testing in vitro. It is worth mentioning that the fused tetrazole derivatives of bile acids may possess better hydrophobic–hydrophilic balance, important for aggregation properties, which could be an interesting topic for future research

Correction: One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

• Giovanna Bosica,
• Kaylie Demanuele,
• José M. Padrón and
• Adrián Puerta

Beilstein J. Org. Chem. 2021, 17, 2026–2027, doi:10.3762/bjoc.17.130

• 10.3762/bjoc.17.130 Keywords: antiproliferative activity; 1,2-dihydropyridines; green Hantzsch synthesis; heterogeneous catalysis; one-pot multicomponent reaction; The authors noticed that the E-factor (E) was calculated using a wrong Equation 2 in the original publication: The correct Equation 2 should

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• (R)-tylocrebrine (32) and (R)-tylophorine (33), which were found to display antiproliferative activity in the nanomolar range against human colorectal carcinoma, human breast carcinoma and drug-resistant human ovarian adenocarcinoma cell lines. Methods for the oxidative homocoupling of phenolic

Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

• Alexei N. Izmest’ev,
• Dmitry B. Vinogradov,
• Natalya G. Kolotyrkina,
• Angelina N. Kravchenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87

• an individual form were found. The methodology proved to be effective for the synthesis of a wide range of target compounds with various substituents in the tricyclic fragment. Investigations of the antiproliferative activity of the synthesized products 4 and 5, as well as possible ways of their

Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

• Ákos Bajtel,
• Mounir Raji,
• Matti Haukka,
• Ferenc Fülöp and
• Zsolt Szakonyi

Beilstein J. Org. Chem. 2021, 17, 983–990, doi:10.3762/bjoc.17.80

• enantioselective transformations, while the 2-phenyliminooxazolidines could be interesting in the field of antiproliferative or antioxidants studies based on our former studies on 2-imino-1,3-heterocycles [42][43]. Biologically active 2-amino-1,3-diols. NOESY experiments and X-ray structure elucidation of

Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues

• Rashmi Singh,
• Tomas Horsten,
• Rashmi Prakash,
• Swapan Dey and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 977–982, doi:10.3762/bjoc.17.79

• multiple natural products [1][2] and have broad applications in areas ranging from medicinal chemistry [1][2][3][4][5][6][7][8][9][10] to materials science [11]. Figure 1 presents a few examples of dibenzofuran-containing molecules. Benzofurocoumarin analogues of 1 have antiproliferative effects on human

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• , antiulcer, anxiolytic, antiherpes agents [115][116][117][118][119]. Similarly, pyrazolo-pyridines are found to be potent antibacterial (131), cytotoxic (132), antiproliferative (133) and antimalarial (134) agents (Figure 10) [120][121]. 8.2.1 Imidazo[1,2-a]pyridine: Sun and co-workers [122] accomplished the

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• Pseudopterogorgia americana in 1972 (Figure 1B) [7], several others from the family have been reported [8][9][10][11][12][13][14]. The 9,11-secosterols exhibit diverse biological activities, including antihistaminic, antiproliferative, anti-inflammatory, cytotoxic and protein kinase C (PKC) inhibition activities [8

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

• Giovanna Bosica,
• Kaylie Demanuele,
• José M. Padrón and
• Adrián Puerta

Beilstein J. Org. Chem. 2020, 16, 2862–2869, doi:10.3762/bjoc.16.235

• preliminary study of the antiproliferative activity against human solid tumor cells demonstrated that 1,2-DHPs could inhibit cancer cell growth in the low micromolar range. Keywords: antiproliferative activity; 1,2-dihydropyridines; green Hantzsch synthesis; heterogeneous catalysis; one-pot multicomponent

• the general procedure. Biological screening The 1,4-DHP scaffold displays an extensive range of biological activities, including reversing multidrug resistance (through the inhibition of the P-glycoprotein) [26] and antiproliferative effects on human cancer cell lines [27]. We wondered whether the

• studied 1,2-DHPs could interfere with tumor cell growth. Thus, we selected a small subset of 1,2-DHPs and screened them against a panel of six human solid tumor cell lines. The results are shown in Table 4. Interestingly, the majority of the 1,2-DHPs displayed antiproliferative activity against all cell

Regioselective cobalt(II)-catalyzed [2 + 3] cycloaddition reaction of fluoroalkylated alkynes with 2-formylphenylboronic acids: easy access to 2-fluoroalkylated indenols

• Tatsuya Kumon,
• Miroku Shimada,
• Jianyan Wu,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 2193–2200, doi:10.3762/bjoc.16.184

• to the insecticidal, myorelaxation, and antiproliferative properties (Figure 1) [1][2][3][4][5][6][7][8][9][10][11][12]. Thus, enormous attention has been paid to 2- or 3-fluoroalkylated indenol derivatives in the field of medicinal and agrochemical drug design since a fluorine atom can very often

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

• Mysore Bhyrappa Harisha,
• Pandi Dhanalakshmi,
• Rajendran Suresh,
• Raju Ranjith Kumar and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

• ][22][23][24][25][26]. Some oxazoles play a significant role in biological properties such as TRPV1 antagonistical activity, antifungal, analgesic, anti-inflammatory, antiproliferative, antileukemia, anticancer [27][28][29][30][31][32] and enzyme inhibitory activities [33][34][35][36][37][38][39][40

Syntheses of spliceostatins and thailanstatins: a review

• William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

• with their complex structure, a number of total syntheses have been reported. This review will compare the synthetic strategies reported through the end of 2019. Keywords: antiproliferative; polyketide natural products; tetrahydropyrans; total synthesis; Introduction The spliceostatins/thailanstatins

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• fully reduced form of BER, namely tetrahydroberberine (THBER), and its derivatives have proven to present different biological activities. Therefore, the obtained arylhydrazono-functionalized DHBERs were reduced to the corresponding arylhydrazono-THBERs. The antiproliferative activity of both

• arylhydrazono-DHBERs and -THBERs has been evaluated on NCI-H1975 lung cancer cells. Keywords: antiproliferative agent; dihydroberberine; hydrazones; reduction; tetrahydroberberine; Introduction The rhizome of Coptis chinensis Franch. is a common remedy in traditional oriental medicine for the treatment of

• ; in particular, we focused our attention on their antiproliferative capacity, due to our previous research experiences on the anticancer properties of both natural and synthetic molecules [39][40][41][42]. A common strategy to increase the biological activity of a class of products can be the

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

• Mio Matsumura,
• Tsutomu Takahashi,
• Hikari Yamauchi,
• Shunsuke Sakuma,
• Yukako Hayashi,
• Tadashi Hyodo,
• Tohru Obata,
• Kentaro Yamaguchi,
• Yasuyuki Fujiwara and
• Shuji Yasuike

Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

• potential antioxidants and showed antiproliferative activity [27][28]. Consequently, they have attracted much attention, and methods for their syntheses have been actively pursued. A powerful method for the synthesis of 3-selanylimidazo[1,2-a]pyridines involves the C–H selenation using imidazopyridine and a

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

• Dong Cai,
• ZhiHua Zhang,
• Yufan Meng,
• KaiLi Zhu,
• LiYi Chen,
• ChangXiang Yu,
• ChangWei Yu,
• ZiYi Fu,
• DianShen Yang and
• YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

• modifications at the C3-OH group of 18β-glycyrrhetinic acid are identified to be relatively common and effective. The modification of the C3-OH group, altering the molecular polarity of 18β-glycyrrhetinic acid, may be an advantage in achieving better cytotoxicity or antiproliferative activity [8][9][10]. For