N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

• -rhamnosides α-17a and α-17c, respectively (Scheme 14) [23]. Water solubility plays an important role with regard to the pharmacological activity. It was previously shown that the water solubility and anticancer activity of non-glycosylated indirubins can be improved by conversion of the keto to an oxime group

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

• Dmitriy Yu. Vandyshev,
• Daria A. Mangusheva,
• Khidmet S. Shikhaliev,
• Kirill A. Scherbakov,
• Oleg N. Burov,
• Alexander D. Zagrebaev,
• Tatiana N. Khmelevskaya,
• Alexey S. Trenin and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

• applications [28][29] including as antifungal agents [30][31][32][33]. These findings are supported by a number of literature sources that highlight the importance of incorporating the acetanilide moiety into potential drugs, including for enhancing the pharmacological activity of imidazo[1,2-a]pyrimidines [1

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• (С3), 118.2 (С4), 128.4 (С6), 136.5 (С5), 141.4 (С2); Anal. calcd for C5H5NO2: C, 53.98; H, 4.67; N, 12.71; found: C, 54.06; H, 4.51; N, 12.62. Derivatives of 6-methyluracil and 2-hydroxypyridine demonstrating pharmacological activity: 5-hydroxy-6-methyluracil (a), 5-hydroxy-1,3,6-trimethyluracil (b

2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

• Carlos Nieto,
• Alejandro Manchado,
• Ángel García-González,
• David Díez and
• Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

• rescaffolding procedures that can be conducted with this unit. In this regard, a review on the use of 2-heteroarylethylamines displaying pharmacological activity is reported. A detailed description of flexible, amine-opened motifs is provided, that describes therapeutic targets and other potent bioactive

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

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• crocins have been elucidated to date, which allows the heterologous production of these valuable compounds in microorganisms by fermentation. This review article provides a comprehensive overview of the chemistry, pharmacological activity, biosynthetic pathways, and heterologous production of crocins

• , aiming to lay the foundation for the large-scale production of these valuable natural products by using engineered microbial cell factories. Keywords: biosynthetic pathway; crocetin; crocins; metabolic engineering; pharmacological activity; Introduction Crocins are hydrophilic apocarotenoids mainly

• pharmaceutical industries [5]. They exhibit a broad spectrum of pharmacological activity, including antitumor [6], anti-inflammatory [7], hepatoprotective [8], nephroprotective [9], antidepressant [10], antioxidant [11], and antidiabetic [12] properties. The Saffron Multi-glycoside Tablet (Xihonghua Zonggan Pian

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

• Yumei Wang,
• Guangzhu Wang,
• Yanping Zhu and
• Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

• increase drug activity by affecting drug receptor interactions [1]. Therefore, replacing hydrogen with one or more fluoro atoms has beneficial effects on therapeutic efficacy and pharmacological activity [2]. For example, flindokalner is a potassium channel opener (Figure 1) [3]. JAB-3068 is a promising

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• dispirobarbiturates containing the indane skeleton has not been reported yet. In light of the prominent bioactivities and the pharmacological activity of the above two framework compounds, the combination of these two species may be potential drug candidates. Therefore, it is of great significance to develop a new

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 (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

• Lukáš Marek,
• Lukáš Kolman,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

• )oxindoles) belong to a subclass of intensively studied heterocyclic compounds, especially due to their significant pharmacological activity. As early as in the middle of the 1980s researchers at Pfizer Inc. patented [1] these compounds as highly potent gabaergic agents, having possible therapeutic utility

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

• Michał M. Więcław and
• Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

• methodology followed by NaBH4 reduction. This structure with three condensed rings can be seen as a new class of unnatural, chiral alkaloid scaffolds, potentially exhibiting pharmacological activity (Scheme 3) [40]. Various unsuccessful attempts were made to deprotect compound 3e. Unexpectedly, however, one of

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

• bring about an increasing effect on the pharmacological activity owing to the unique nature of the fluorine atom(s) [13][14][15][16][17][18]. However, reports on a synthetic protocol for 2- or 3-fluoroalkylated indenols are very limited [19][20][21][22]. Recently, Yamazaki et al. have reported the

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

• Carlos H. Escalante,
• Eder I. Martínez-Mora,
• Carlos Espinoza-Hicks,
• Alejandro A. Camacho-Dávila,
• Fernando R. Ramos-Morales,
• Francisco Delgado and
• Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

• that are known to have varied and robust pharmacological activity, such as isoborreverine (1) [12], mitomycin A (2) [13] and chlorizidine A (3) [14]. The indole moiety is incorporated into their structure, which is important because it is a seminal heterocycle that exhibits a wide range of biological

• stereoselective approaches of substrates and reagents or catalysts in a variety of processes. Examples include the substrate–enzyme recognition (the host–guest interaction) responsible for inducing pharmacological activity, the DNA-intercalation capable of generating biomolecular activity, molecular dynamics [63

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

• Abimelek Cortes-Pacheco,
• María Adelina Jiménez-Arellanes,
• Francisco José Palacios-Can,
• José Antonio Valcarcel-Gamiño,
• Rodrigo Said Razo-Hernández,
• María del Carmen Juárez-Vázquez,
• Adolfo López-Torres and
• Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

• final products 3–6, respectively, in 41–73% yield (Scheme 2). Pharmacological activity With the target compounds on hand, we proceed to evaluate them with two acute inflammation models: a) 12-O-tetradecanoylphorbol-13-acetate (TPA) through topical administration [25] and b) a carrageenan model, through

• the pharmacological activity. More important was the replacement of the aliphatic for an aromatic residue in the ester group, leading to the more active derivatives 5 and 6. The clogP value of 5 and 6 was more similar between them, but a remarked difference in the edema inhibition was observed (40.7

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• ; photocycloaddition; Introduction Truxillic acid derivatives (Figure 1a) are a special family of cyclobutanes that have been known since 1888 and show properties of high interest [1]. In this respect, their pharmacological activity has prompted extensive research that has focused on both their synthesis and the

• applications as internal donors in Ziegler–Natta catalysts for polymerization [14] or as building blocks in polymer chemistry [15]. A very closely related group of cyclobutanes are the 1,3-diaminotruxillic ester derivatives (Figure 1b). This type of bis-amino esters also shows remarkable pharmacological

• activity, not only as antinociceptive drugs but also in the treatment of type 2 diabetes mellitus. In fact, recent results have shown that these compounds are the only non-peptidic agonists of the GLP-1R (glucagon-like peptide 1 receptor) and they have a higher stability than any other agonist prepared to

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

• Xiaodong Zhang,
• Jun Xie,
• Zhiling Xu,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

• ; inclusion complex; properties; Introduction Baicalein (5,6,7-trihydroxyflavonoid) has a molecular formula of C15H10O5 (BALE, Figure 1) and is a natural flavonoid found in the roots of Scutellaria baicalensis Georgi [1]. The compound displays pharmacological activity such as antimicrobial, anti-inflammatory

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• androstanic steroids. Such heterocyclic moieties are of interest because of their pharmacological activity, for example, as anti-inflammatory agents. Employing epiandrosterone and benzaldehyde as oxo components, ammonium acetate and malononitrile as C-nucleophile, the authors produced 2-amino-3-cyano-1,4

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• recently from an extract of Pseudoceratina Sp. [6]. The variety of types of pharmacological activity revealed in these marine sponges’ metabolites is not inferior to the chemodiversity of their structure. Many of them are reported to have properties such as α-adrenoreceptors [7] and leukotriene B4 receptor

Asymmetric synthesis of a high added value chiral amine using immobilized ω-transaminases

• Antonella Petri,
• Valeria Colonna and
• Oreste Piccolo

Beilstein J. Org. Chem. 2019, 15, 60–66, doi:10.3762/bjoc.15.6

• boiling point byproduct acetone [2][3][4][5][6]. Since (R)- and (S)-selective TAs are available on the market, both enantiomers of the amine product are accessible. This point is particularly relevant since in most cases the pharmacological activity of a chiral drug is closely related to its absolute

Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

• Mario Pérez-Venegas,
• Gloria Reyes-Rangel,
• Adrián Neri,
• Jaime Escalante and
• Eusebio Juaristi

Beilstein J. Org. Chem. 2017, 13, 1728–1734, doi:10.3762/bjoc.13.167

• preparation of β-amino acids, especially protocols leading to products with high enantiomeric excess (ee), which are required to test the pharmacological activity of each enantiomer [11][12][13]. In this regard, several methods for the asymmetric synthesis of β-amino acids have been documented [14][15][16][17

Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

• Lina Jia and
• Fuzhong Han

Beilstein J. Org. Chem. 2017, 13, 1425–1429, doi:10.3762/bjoc.13.139

• [3][4][5], exhibit a broad spectrum of pharmacological activity, such as antibacterial, anti-HIV, antifungal, antibiotic, antitumor and immunosuppressive effects [6][7][8][9][10]. In addition, the one-pot cascade transformation has proven to be the key step in organic syntheses because of its broad

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

• HepG2 cells). The LDH release was accompanied by a significant increase in cell death, as detected by flow cytometry through a propidium iodide assay (Figure 8b) [50][51]. Involvement of p53 in the pharmacological activity Tumor suppressor p53 plays an important role in conserving genome stability by

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• , the use of fluorescent probes requires the covalent binding of large dye molecules (bodipy, cyanine, rhodamine etc, ...) to the drug conjugate, thus potentially modifying its physicochemical profile as well as the in vivo fate and the pharmacological activity. A simple encapsulation of an amphiphilic

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

• discussed. Thirteen representatives from eight different natural or natural-like phenolic subclasses are presented with an emphasis on their synthesis and methods to modify the parent compounds. When available, the consequence of structural variation on the pharmacological activity of the molecules is

• therapy of pathologically-induced angiogenesis [7][8]. Among such natural products, phenolic or polyphenolic compounds with anti-angiogenic properties have been investigated and the opinion regarding their potential pharmacological impact has changed over the years. While the pharmacological activity of

• , specifically addressing their chemistry, synthesis and possible structure modifications. Nevertheless, it should be mentioned that the selection of compounds for this review is based on the reports of their pharmacological activity. As the term “anti-angiogenic compound” is not clearly defined and somewhat

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer

• Florian Hamon,
• Claire Blaszkiewicz,
• Marie Buchotte,
• Estelle Banaszak-Léonard,
• Hervé Bricout,
• Sébastien Tilloy,
• Eric Monflier,
• Christine Cézard,
• Laurent Bouteiller,
• Christophe Len and
• Florence Djedaini-Pilard

Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

• well-defined structure, low toxicological or pharmacological activity, and good solubility in water. For example, the inclusion of active substances in CDs can reduce their undesirable storage or metabolism degradation, which has led research on CDs to focus on controlled drug delivery [4]. In the food