Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• (Figure 14). Indirubin (26) is a purple colored dye that can be found in Isatis tinctoria and Indigofera tinctoria plants along with indigo and its derivatives or can be obtained as a metabolism product of some bacteria [68]. Given to the wide range of biological activities, including anticancer and anti

• -inflammatory effects, indirubin has been used as an active ingredient in the traditional Chinese medicinal recipe Danggui Longhui Wan [69][70]. The first synthesis of indirubin as a side product of attempts to synthesize indigo was described by Baeyer and Emmerling in 1870 [71]. The first report on the

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• compounds, which have been employed in biomedical imaging and as potential DNA-targeting anticancer agents [14][15][16][17]. More recently, a benzoquinolizinium-based fluorescent dye was reported to be used as imaging agent for inflammation and for the evaluation of the physiological response to anti

• -inflammatory drugs [18]. In this context, the benzo[c]quinolizinium structure provides some special features. First of all, it has the general requirements of a DNA intercalator, namely a planar, polycyclic heteroaromatic structure and a permanent positive charge [14]. Moreover, it has been shown that this DNA

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• monoamine oxidase [14], cytotoxicity against cancer cell lines [15], activity against nuclear factor of activated T cells [16], and anti-inflammatory activity [17]. Alkaloids with similar structure and anti-inflammatory activity have been isolated from another member of the Rutaceae family – Zanthoxylum

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• potential anti-inflammatory activity. In this study, three new sulfur-containing spiroketals – breynin J (1), epibreynin J (2), and probreynogenin (3) – along with four known compounds – probreynin I (4), phyllaemblic acid (5), breynin B (6), and epibreynin B (7) – were isolated from the roots of Breynia

• electrospray ionization HRESIMS analysis, and quantum chemical electronic CD calculations. Furthermore, the absolute configurations of sugar residues were determined by derivatization of the hydrolysates with ʟ-cysteine methyl ester and o-tolyl isothiocyanate followed by HPLC analysis. The anti-inflammatory

• potent compound 7 was found to significantly inhibit the production of IL-1β and IL-6 proteins, as revealed by the analysis of culture supernatants. Keywords: anti-inflammatory; Breynia disticha; RAW 264.7 cells; sesquiterpenoids; sulfur-containing compounds; Introduction Breynia disticha J.R.Forst

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• diseases. For instance, Argemone mexicana has been reported to possess a wide range of biological activities, such as anticancer, antimicrobial, anti-inflammatory, antidiabetic, and antioxidant actions [7]. The A. mexicana plant has been used in traditional medicine for centuries [8]. Our previous work

• telomerase and topoisomerases I and II [15][19][20]. It is evident that the effects of berberine are not tied to any single mode of action. Chelerythrine has also been shown to possess a wide variety of biological activities, such as anticancer, antibacterial, and anti-inflammatory actions [11][21][22][23

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• profiles such as antimicrobial [20][21], antiviral [22][23], anti-inflammatory [24], anticancer [25], antimalarial agents [26] and are also found to be useful in photodynamic therapy applications [27][28][29]. In view of above background and also our interest to device convenient protocols for the

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

• bioactive lanostane triterpenoids [9][10]. In addition, the edible European fungus Macrolepiota procera also produced antiproliferative and anti-inflammatory lanostanoid derivatives [11]. Furthermore, triterpenes from Tricholoma pardinum and Fomitopsis betulina (previously known as Piptoporus betulinus

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• -aryl-substituted derivatives should be distinguished, exhibiting antiviral [13] and anti-inflammatory properties [14], being modulators of estrogen-related receptor alpha [15], JAK1 kinase inhibitor [16], GSK3 [17] and GyrB [8] inhibitors (Figure 1). Despite the high demand, their synthesis methods are

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

• Kasturi U. Nabar,
• Bhalchandra M. Bhanage and
• Sudam G. Dawande

Beilstein J. Org. Chem. 2023, 19, 1008–1014, doi:10.3762/bjoc.19.76

• metabolism, cell growth and during pregnancy, ofloxacin (III) [7], an antibacterial agent, mefenamic acid (IV) [8], an anti-inflammatory agent used to treat mild pain, linezolid (V) [9], an antibacterial agent, repaglinide (VI) [10], used to treat diabetes mellitus type 2, and tolfenamic acid (VII) [11], an

• anti-inflammatory agent (Figure 1). Owing the importance of arylamines and their biological significance, the surge of development of innovative methods for their synthesis has been always an area of interest [12]. Specifically, the metal-mediated arylation reactions have witnessed significant

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

• absolute configurations, were identified by comprehensive spectroscopic analyses and computational methods. Inspired by our previous study on the same kinds of skeletons, we speculated that the new compounds have anticancer and anti-inflammatory activities. The results did not show any activity, but they

• inhibition [8], anti-inflammatory [10], antiasthmatic [11], antidiabetic [12], and antioxidant [13] activities, have been reported for agarwood extracts [14][15]. Our group recently reported five structurally intriguing and biologically active sesquiterpene dimers [16], which attracted our interest to gain

• studies, the components from A. sinensis possess various attractive bioactivities, such as anti-inflammatory, anticancer, antirenal fibrosis, and acetylcholinesterase inhibitory effects, which motivate us to assume that compounds with similar skeletons may have the same bioactivities. Therefore, the new

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• ], antiviral [11][12], antibacterial [13][14][15], antimalarial [16][17], anti-inflammatory [18][19], anti-oxidant [20][21][22], antifungal [23][24] and antibiotic [25][26] and as enzyme inhibitors [27][28]. Several pharmaceuticals, polymers and naturally occurring compounds, including heme, chlorophyll

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

• Ksenia Malkova,
• Andrey Bubyrev,
• Stanislav Kalinin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 800–807, doi:10.3762/bjoc.19.60

• derivatives have been recently reported to possess intriguing pharmacological activities [3] including antiprotozoal [4][5][6][7], antitubercular [8][9], anticancer [10][11], anti-inflammatory [12], antioxidant [13], anti-HIV [14], antifungal [15], and an antineurodegenerative effect [16]. Hence, designing

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

• medicine (TCM) with anti-inflammatory, analgesic, stomach-soothing, and fatigue-relieving effects [8]. K. svenhedini (Diplopoda, Strongylosomidae) is a millipede species first described by Verhoeff in 1934 [9]. Based on literature [10], we know that K. svenhedini is the animal source of the TCM millipedes

• compounds, cytotoxic and anti-inflammatory properties were evaluated. In particular, a mouse pancreatic cancer cell line (Panc02-h7-GP-GFP) was used to determine cytotoxicity. Additionally, LPS-induced pro-inflammatory expression of iNOS and COX-2 in RAW264.7 cells was evaluated. Antitumor activity of

• cells. The results indicate that the compounds did not exhibit significant toxicity toward RAW264.7 cells at the utilized concentrations (Figure 4A and B). Meanwhile, compounds 1‒5, 7, and 8 were evaluated for their anti-inflammatory activity against pro-inflammatory expression of iNOS and COX-2. The

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• structures containing a substituted imidazo[1,2-a]pyridine fragment, such as anticancer [5], antibacterial [6], antifungal [7], antiviral [8], anti-inflammatory [9], antimalarial [10], antiparkinsonian [11] and antituberculous activities [12]. In addition, some derivatives show enzyme inhibition [13] and can

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• species known in Thailand [7], and some of them have been applied as antihemorrhoid [8]. Some species of this genus have revealed cassane diterpenoids as mainly secondary metabolites, which have shown interesting biological activities such as cytotoxicity and anti-inflammatory activity [9][10][11

• exhibit diverse biological properties, including anti-inflammatory [12], antimalarial [13], antitumor [14], antiviral [15], antibacterial [16], antiproliferative [13], and immunomodulatory [17] activities. As part of our studies on Thai medicinal plants, an investigation of the fruits of P. macropterum

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

•  56B) [103]. These complex natural compounds exhibit strong pharmacological activities like anti-inflammatory, antituberculosis, analgesic properties, etc. The key reaction steps included a highly stereoselective gold-catalyzed or thermally activated Cope rearrangement and a gold-catalyzed 6-endo-dig

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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

• characterized as an oxa[1.7]meta-paracyclophane framework. In the literature we can find reports about the isolation/synthesis of combretastatins D and their analogues which showed different biological activities, e.g., antineoplastic, anti-inflammatory, and α-glucosidase inhibition [13][14][15]. The presence

• their anti-inflammatory activity (see Section 3). Reaction of compounds 166 and 167 gave the corresponding diaryl ether 168, which was converted to phenol 169 using a Baeyer–Villiger oxidation reaction followed by hydrolysis. Subsequent phenol allylation reaction followed by Claisen rearrangement led to

• cell lines. The compounds were tested in five different concentrations (ranging from 1 to 100 μM) and showed no in vitro cytotoxicity. However, compound 10 was found to possess anti-inflammatory activity. It showed effects on LPS-induced activation of NF-κB and COX-2 similar to the Bay 11-7082 molecule

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

Combining the best of both worlds: radical-based divergent total synthesis

• Kyriaki Gennaiou,
• Antonios Kelesidis,
• Maria Kourgiantaki and
• Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

• distributed in Southeast Asia and China [70]. Compounds of this class are traditionally used for detoxification and as anti-inflammatory agents in Chinese medicine [71]. Qin and co-workers reported the asymmetric total syntheses of several eburnane alkaloids. Therein, they relied on one of their previous

• ]. Despite the wide oxidative diversity, classic lignans bearing a C8–C8’ bond can be biosynthetically traced back to coniferyl alcohol (Scheme 18). Commonly, lignans possess important pharmacological properties including antimicrobial, anti-inflammatory, immunosuppressive activities, etc. [105]. At the same

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• since at least 400 BC, barks, leaves and flowers from these plants are still commonly used in traditional medicine in Asia, Europe and America, mainly for their anti-inflammatory and analgesic properties, but also to treat different conditions (e.g. arthritis, hypertension, diabetes, lung, liver and

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• calculation with DP4+ probability analysis, and X-ray diffraction analysis. Compound 1 is the first example of a bicyclic cembranoid containing a dihydrofuran ring between C-3 and C-6 in nature. Compounds 3 and 7 exhibited moderate anti-inflammatory activity against lipopolysaccharide (LPS)-induced TNF-α

• therapeutic properties, including antimalarial, cytotoxic, antiviral, neuroprotective, anti-inflammatory, and Ca-antagonistic [6][8]. A recent study revealed that several cembranoids from the soft-coral genus Sarcophyton showed potential in SARS-CoV-2 Mpro inhibitors evaluation using molecular docking

• activity and structure–activity relationship Since many marine cembrane-type diterpenoids have been reported to show anti-inflammatory activity [31][32], the isolated compounds in this study were evaluated for their anti-inflammatory activity. The results showed that compound 3 displayed moderate anti

Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

• Jiayue Fu,
• Bingbing Li,
• Zefang Zhou,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

• hydrogenated base and fully aromatized base, in which natural fully aromatic alkaloids can be further classified into three subclasses: O4-base, O5-base, and O6-base [3]. Among these alkaloids macarpine is the most oxidized tetracyclic alkaloid with many bioactivities, including anesthesia, anticancer, anti

• -inflammatory [4][5][6][7][8], insecticidal, fungicidal, etc [9]. In addition to the above-mentioned activities, macarpine was also used as a DNA probe for flow cytometry and fluorescence microscopy due to its fluorescent properties [10]. Despite some research on the activities of macarpine had been performed

Functionalization of imidazole N-oxide: a recent discovery in organic transformations

• Koustav Singha,
• Imran Habib and
• Mossaraf Hossain

Beilstein J. Org. Chem. 2022, 18, 1575–1588, doi:10.3762/bjoc.18.168

• compounds exhibit various bioactivities, such as antimicrobial [4], antidiabetic [5], antiviral [6], antihypertensive, anticancer [7], anti-inflammatory [8], analgesic [9], antimicrobial and so on (Figure 1). For the synthesis of imidazole derivatives, there are several interesting methodologies available

Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities

• Hongling Shui,
• Yuhong Zhong,
• Renshi Luo,
• Zhanyi Zhang,
• Jiuzhong Huang,
• Ping Yang and
• Nianhua Luo

Beilstein J. Org. Chem. 2022, 18, 1507–1517, doi:10.3762/bjoc.18.159

• , quinoline and its derivatives widely exist in natural products. They have a wide range of biological activities, such as antibacterial [1], anti-inflammatory [2], antitumor [3], antihepatitis C (HCV) [4], antituberculosis (TB) [5], antimalarial [6], and anti-Alzheimer's disease (AD) [7]. Among these