4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Luc Van Meervelt,
• Do Thi Thao and
• Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

• well as ADMET properties. All compounds satisfied these criteria, indicating favorable oral bioavailability. Molecular docking analysis showed that compounds 5a–e act as ligands for inducible nitric oxide synthase (iNOS), especially with Cys200 and Ser242 via hydrogen bonds. In addition, van der Waals

• interactions also contribute to the stabilization of the ligand–iNOS complexes. In particular, 4-(1-methylamino)ethylidene-5-phenyl-1-(3-nitrophenyl)pyrrolidine-2,3-dione (5e) exhibited the strongest binding affinity (−9.51 kcal/mol) and demonstrated significant inhibitory activity against nitric oxide (NO

• derivatives; iNOS; pyrrolidine-2,3-dione derivatives; pyrrolidine-2,3-diones; pyrrolidine-2,3-diones targeting reversible transimination reaction; Introduction Nitric oxide (NO) is an important signaling molecule in numerous physiological processes such as neuronal tranmission, immue response, inflammatory

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• of the biological activity and to find biomedical applications, different releasing systems of this anion are developed. The peroxynitrite anion is formed by coupling of nitric oxide (NO) and the superoxide (O2•−). An efficient system has been developed to realize this reaction (Scheme 16) [74]. In a

• photocatalyst 62 favors its incorporation in the nanoparticles. Thus, both reaction partners are approached. A similar photocatalytic system has been developed for the release of nitric oxide (Figure 15) [76]. Meanwhile, numerous applications of the NO release to medicine have been studied [77]. In the present

• method has been developed in the context of the treatment of intervertebral disc degeneration caused by bacterial infection. It also inhibits the inflammatory response and osteoclast differentiation in the intervertebral disc tissues. The present coumarin derivative is also capable of releasing nitric

Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide

• Parvathy Mini,
• Michael R. Grace,
• Genevieve H. Dennison and
• Kellie L. Tuck

Beilstein J. Org. Chem. 2024, 20, 2818–2826, doi:10.3762/bjoc.20.237

• hydrogen sulfide. Hydrogen sulfide (H2S) is now recognised as a significant gaseous signaling molecule, alongside nitric oxide and carbon monoxide; it belongs to the biologically active group known as "gaseous mediators" or "gasotransmitters" [1]. In mammalian systems, H2S is predominantly biosynthesized

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

• Yuri A. Sidunets,
• Valeriya G. Melekhina and
• Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

• thermostable components of functional organic materials. Keywords: molecular hybridization; nitric oxide; nitrogen heterocycles; 1,2,5-oxadiazoles; 1,2,3-triazin-4-one; Introduction Nitrogen heterocycles are a significant and broad class of organic substances included in the structure of various natural

• conditions and do not demonstrate nitrate tolerance. Nitric oxide (NO) is a signaling molecule that plays a key role in numerous physiologic and pathologic processes. Thus, NO regulates blood flow and tissue oxygenation, so disruption of the production and transport of NO in the vascular system leads to

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• ] and Alternaria sp. [28][47][154] (Figure 8). It showed antioxidant activity with an IC50 value of 42.8 μM [153], inhibited about 90% of iNOS (inducible nitric oxide synthase) expression when applied at 20 μM, decreased the protein expression levels of pro-inflammatory cytokines (tumor necrosis factor

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• A and B (54, 55), which were discovered by co-culturing Nocardia uniformis IFM0856T and J774.1 cells [124][125]. Uniformides were shown to suppress the production of nitric oxide, IL-6, and IL-1β by inhibiting the NF-κB pathway. Because NF-κB signaling plays a central role in the immune response

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

• expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX2) [11]. Crocins can also regulate the Nrf2 signaling pathway to protect the brain, liver, and other organs and decrease the expression of pro-inflammatory factors, such as TNF-α, prostaglandin E2 (PGE2), interleukin-1β (IL-1β

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

• ) exhibited nitric oxide (NO) and/or cytotoxic effects, respectively [12][13]. The genus Fomitopsis was first coined by Karsten typified by F. pinicola [14]. Our current study fungus F. carnea was reported for the first time from Japan in 1943 by Blume and Nees [15]. Later, Ryvarden and Johansen in 1980 [16

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• on LPS-induced nitric oxide production in RAW 264.7 macrophages. Keywords: lignan derivatives; nitric oxide production inhibition; norlignans; Selaginella sinensis; Introduction Selaginella is the only genus of Selaginellaceae. As a representative of the earliest and still-surviving vascular plant

• investigated. As a result, three new lignan derivatives 1–3 together with three known lignan glycosides 4–6 (Figure 1) were isolated. Their isolation, structural elucidation and inhibitory effects on LPS-induced nitric oxide production are reported. Results and Discussion Sinensiol H (1) was isolated as a pale

• , 1593.0, 1241.6, 814.9 cm−1; 1H and 13C NMR data, see Table 1; HRESIMS (m/z): [M + COOH]− calcd for C20H23O8, 391.1398; found, 391.1394. Nitric oxide production inhibitory assay The inhibitory activity against the production of NO was evaluated using LPS induced RAW 264.7 cells as previously reported [24

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• structure elucidation was performed for the five new compounds (1–5) using 1D and 2D NMR, HRESIMS, DP4+ and ECD calculations, and chemical methods. All the isolates (1–9) were assessed for their antineuroinflammatory activities on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells

• activities. The antineuroinflammatory activity of all isolates (1–9) was assessed by measuring nitric oxide (NO) production levels in LPS-stimulated murine microglia BV-2 cells (Table 4). Compounds 2 and 5–7 significantly reduced NO levels, with IC50 values of 52.21, 47.90, 61.61, and 25.35 μM, respectively

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

• Md Imran Hossain,
• Md Imdadul H. Khan,
• Seong Jong Kim and
• Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

• with 95% yield (5% water, 95% methanol, room temperature, 2 hours; see Table 1, entry 15), which adds another method for the synthesis of furoxans to the current literature. The synthesis of furoxans or 1,2,5-oxadiazole-2-oxides was first reported by Kekulé in 1857 [36]. Since then, these nitric oxide

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• for the first time. All co-isolates were evaluated for their in vitro inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells. The antibacterial activity of the selected compounds was also tested. Our work enriches the structure

• ], compounds 1−17 were evaluated for their inhibitory activities against LPS-induced nitric oxide (NO) production in RAW 264.7 mouse macrophages. All of them showed mild inhibitory activities with inhibition rates of 10–20% at a concentration of 50 μM (Table 2). Since coumarin derivatives were reported to have

• against nitric oxide (NO) production in LPS-stimulated RAW 264.7 mouse macrophages. The antibacterial activities of compounds 1–4 against Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa were also tested, however, none of them showed

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

• ). Other naphthoquinone derivatives were synthesized with modifications at one of the carbonyls. Tseng and co-workers [91] synthesized 4-arylamino-1,2-naphthoquinones 45a,b and 4-phenoxy-1,2-naphthoquinones 47a,b as potential anti-inflammatory agents capable of inhibiting the expression of nitric oxide (NO

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• on nitric oxide (NO) production levels in lipopolysaccharide (LPS)-stimulated murine microglial BV-2 cells to evaluate for antineuroinflammatory activities (Table 3). Compound 14 showed relative inhibitory effects on NO production with an IC50 value of 20.9 μM which was stronger than the positive

• form, Sigma-Aldrich, St. Louis, MO, USA) using deionized water to remove KOH. A portion of the reaction product was partitioned between EtOAc/H2O (each 1.0 mL) and the aglycone 16a was acquired from the EtOAc-soluble phase. Measurement of nitric oxide production and cell viability. In a manner similar

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

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• ][37][38][39][40]. The acquired cytotoxicity data of compounds 9–11 are consistent with the previous studies. The other compounds 1–8 and 12 showed no activity (IC50 > 30 μM). The potential antineuroinflammatory activity of the compounds 1–12 was tested by measuring the nitric oxide (NO) production

• evaluated with 0.1% N-1-naphthylethylenediamine dihydrochloride and 1% sulfanilamide in 5% phosphoric acid, aka the Griess reagent. The supernatant (50 μL) was mixed with the Gries reagent (50 μL) and after 10 min the absorbance was gauged at 570 nm. For a positive control, the reported nitric oxide

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

• Dandan Li,
• Naoya Oku,
• Yukiko Shinozaki,
• Yoichi Kurokawa and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

• tuberculosis H37Ra at IC90 6.8 μM while weakly cytotoxic to MRC-5 human lung-derived fibroblasts with GI50 84.7 μM [30]. It did not inhibit the production of nitric oxide in RAW 264.7 murine macrophage-like cells [31]. In our hands, 1 was inactive against any of the tested strains including Staphylococcus

Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

• nitroimine (10, 20%), and pivalonitrile (11, 4%) [45]. The proposed scheme for the decomposition of di-tert-butyliminoxyl radical (8) is presented in Scheme 3 [35][45]. It includes formation of C–O dimer 4f followed by the fragmentation to iminyl radical 12, ketone 9, and nitric oxide. The formation of

• nitroimine 10 is explained by the interaction of oxime radical 8 with nitric oxide. Pivalonitrile (11) is presumably formed via β-scission of iminyl radical 12 (Scheme 3). During the decomposition of oxime radical 8 an EPR signal typical for a dialkyl aminoxyl radical (type I in Figure 1) was also observed

Exploring the scope of DBU-promoted amidations of 7-methoxycarbonylpterin

• Anna R. Bockman and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2020, 16, 509–514, doi:10.3762/bjoc.16.46

• , pterins have been a useful scaffold in the development of inhibitors of ricin [3][4], methionine synthase [5], nitric oxide synthase [6], shigella [7], and aldose reductase [8], as well as for treatment of leishmaniosis [9]. In addition to their therapeutic potential, pterin derivatives have been an

A review of the total syntheses of triptolide

• Xiang Zhang,
• Zaozao Xiao and
• Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

• pathways involved in the regulation of reactive oxygen species (ROS) and/or nitric oxide (NO) [9], histone methyltransferase [10], HSP70 [11], Jak2, Bcl-2/Bax [12], caspase 8 [13], NF-κB [14], X-linked inhibitor of apoptosis protein (XIAP) [15], MAPK, PI3K [16], and MPK1, ERK-1/2, and JNK-1/2 [17]. The

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• , antioxidant, antiprotozoal, antiviral and immunobiological activities (reviewed in [1][2]). Two SLs remarkable for their immunobiological potential are archangelolide (1) and trilobolide (2), depicted in Figure 1. Compound 2 exhibits strong induction of nitric oxide (NO) in eukaryotic cells, which in turn

Synthesis of 9-O-arylated berberines via copper-catalyzed C_Ar–O coupling reactions

• Qiaoqiao Teng,
• Xinhui Zhu,
• Qianqian Guo,
• Weihua Jiang,
• Jiang Liu and
• Qi Meng

Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161

• elaborate motifs such as heterocycles [10][11][12], glucose [13], nitric oxide [14], and the multidrug-resistance pump inhibitor 5-nitro-2-phenylindole (INF55) [15] have been covalently attached to BBR, further widening its pharmacological spectrum. Aromatic rings are another family of substituents having

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

• antagonists [8], cyclin-dependent kinases GSK-3β, CK1 [9] and nitric oxide synthase activity inhibitors [10][11], as well as antibacterial [2], antifungal [12], antihistamine [13] and antitumor activities [14]. Remarkable immunosuppressive properties are inherent to palau’amine (VI) [15]. Ceratamines XIII are

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• pathogenesis, the parasite infects and propagates in immune cells, the very cells responsible for host protection. Through a range of mechanisms not entirely understood, Leishmania subverts activation of antimicrobial (nitric oxide) and cytokine inducible functions that initiate effective immunity [5]. There