Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

• analogues of γ-lactams, showing various biological activities, such as anti-inflammatory [15][16], antioxidant [17][18], and antitumor [18][19][20] (Figure 1). Various synthetic methods of 1,2-azaphospholidine 2-oxide and 1,2-azaphospholine 2-oxide derivatives have been developed to date. Two major

• -phenyl-3-phenylamino-2,3,3a,9a-tetrahydro-4H-1,2-azaphospholo[5,4-b]chromen-4-one (215) in 44% yield through the Michael addition and subsequent intramolecular aminolysis (Scheme 34) [15]. The products are potential anti-inflammatory agents. In 2013, to develop potent anti-inflammatory agents, Abdou and

DDQ in mechanochemical C–N coupling reactions

• Shyamal Kanti Bera,
• Rosalin Bhanja and
• Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

• ][50], antimalarial [51], anti-inflammatory [52], etc. We therefore investigated the scope of the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes in the presence of DDQ under the optimized mechanochemical conditions and the results are shown in Figure 3. Unsubstituted anthranilamides

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

• enhanced the biological activities like anticancer [15][16], antibacterial [17], antimalarial [18], anti-inflammatory [19], and lead to a promising scaffold for the treatment of Alzheimer’s disease [20]. Our previous work showed that a combination between cholic acid and heterocyclic scaffolds improved the

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

• , lignans, flavonoids, and phenolic compounds that show anti-inflammatory, cytotoxic, and/or cytoprotective effects [3][4][5][6][7]. However, bioactive terpenoids of G. hederacea var. longituba with antineurodegenerative effects remain largely unknown. In this study, nine terpenoids (1–9) including five new

Sesquiterpenes from the soil-derived fungus Trichoderma citrinoviride PSU-SPSF346

• Wiriya Yaosanit,
• Vatcharin Rukachaisirikul,
• Souwalak Phongpaichit,
• Sita Preedanon and
• Jariya Sakayaroj

Beilstein J. Org. Chem. 2022, 18, 479–485, doi:10.3762/bjoc.18.50

• Trichoderma citrinoviride produces structurally diverse secondary metabolites including diterpenes [1][2], alkaloids [3], sorbicillinoids [4][5], long chain alcohols [6], and cyclonerane sesquiterpenes [7]. Some of them display antibacterial [1][2][7], cytotoxic [3], anti-inflammatory [4], and antimicroalgal

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

• and γ-amino alcohols [1]. Isoxazoles, appearing in 33 patents from the year 2016 to 2018 [3], are an important drug class due to their wide range of biological activities, such as anticancer [5], antibiotic [6][7], antimicrobial [8], antifungal [9], and anti-inflammatory [10]. Therefore, new methods

Four bioactive new steroids from the soft coral Lobophytum pauciflorum collected in South China Sea

• Di Zhang,
• Zhe Wang,
• Xiao Han,
• Xiao-Lei Li,
• Zhong-Yu Lu,
• Bei-Bei Dou,
• Wen-Ze Zhang,
• Xu-Li Tang,
• Ping-Lin Li and
• Guo-Qiang Li

Beilstein J. Org. Chem. 2022, 18, 374–380, doi:10.3762/bjoc.18.42

• addition, compound 1 also showed a moderate anti-inflammatory effect in zebrafish. Keywords: anti-inflammatory; cytotoxicity; Lobophytum pauciflorum; soft coral; steroids; X-ray diffraction; Introduction The unique and complicated marine environment makes soft corals a treasure-house of secondary

• containing side chains with 23,24-dimethyl groups and (17)20E double bond, have been reported to be frequently isolated from soft corals of this genus, some of them exhibited anti-inflammatory [4], cytotoxic [5][6], and antibacterial activities [7]. To search for bioactive natural products, we have

• value of 19.03 μM. The investigation of anti-inflammatory activities of lobophysterols E–H with classic transgenic fluorescent zebrafish models (Figure 5) showed that compound 1 exhibited moderate activity, with an inhibition rate of 32% (20 μM). Conclusion In conclusion, four new steroids

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

• Sangram Gore,
• Sundarababu Baskaran and
• Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

• ][3][4]. The dihydropyrimidinone structure is found in calcium channel blockers [5][6][7], α1a adrenoceptor-selective antagonists [8][9], antihypertensive [10][11][12][13] and anti-inflammatory agents [14][15]. An interesting example is a rather simple DHPM derivative, monastrol, which specifically

Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study

• Angel Ho,
• Austin Pounder,
• Krish Valluru,
• Leanne D. Chen and
• William Tam

Beilstein J. Org. Chem. 2022, 18, 251–261, doi:10.3762/bjoc.18.30

• intermediates have found use in the total synthesis of (+)-norchelidonine (an isoquinoline alkaloid) [55], sertraline (an antidepressant) [56], and arnottin I (an anti-inflammatory) [57]. Although OBD 1 has been shown to undergo many different modes of reactivity in both a stereo- and enantioselective manner

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

• extracts and chemical constituents produced by Wikstroemia species, including cardiovascular, neuroprotective, hepatoprotective, anti-inflammatory, and antitumor activities [1][3]. The plant species W. nutans is widely distributed in the areas of the Guangdong and Guangxi provinces of China, and the whole

• large quantity of phenolic substances found in plants and microorganisms [5]. These naturally occurring coumarins were well documented due to their diverse chemical structures and promising biological properties, such as anticancer, antitubercular, anti-inflammatory, anticoagulant, antibacterial, and

• ) [25] (Figure 1) by comparison to literature data. In addition, compounds 2, 3, 8, and 11 were isolated for the first time from the genus Wikstroemia. Biological activity Considered naturally occurring glycosides of phenolic metabolites usually exhibit anti-inflammatory activity in literature [26

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• scaffolds with versatile medicinal properties, including anti-Alzheimer, anti-inflammatory, anticancer, antidiabetic, and antileishmanial activity [1]. Since the first synthesis of paullones (scaffold A in Figure 1) in 1992 [2], and disclosure of their Cdk inhibiting potential, several other analogues were

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 [82] synthesized and evaluated several 1,2-naphthoquinones substituted at position C4 with alkyl- or arylamino groups for their inhibition of the PTP1B protein. Furthermore, to discover new effective anti-inflammatory and analgesic agents, Gouda and co-workers [83] synthesized various compounds in

• good yields from the reaction of β-NQS 18 with 2-amino-5-selenothiazoles, such as 33 and 34. The authors reported that most of the compounds tested had similar anti-inflammatory properties or greater activity than meloxicam (Scheme 8). β-Lapachone (11) is a potent reversible inhibitor of the liver

• ). 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

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

• Chuanhua Qu,
• Run Huang,
• Yong Li,
• Tong Liu,
• Yuan Chen and
• Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

• ; isonitrile diarylmethane; synthetic utility; Introduction Sulfones are ubiquitous units commonly found in marketed drugs and natural products. Because of their unique electronic and structural properties, they are often used in medicinal chemistry programs to search for anti-inflammatory, anti-HIV

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

• Alla I. Vaskevych,
• Nataliia O. Savinchuk,
• Ruslan I. Vaskevych,
• Eduard B. Rusanov,
• Oleksandr O. Grygorenko and
• Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

• anti-inflammatory [9], antibacterial [10], antiarrythmic [11] activity; some representatives are CNS suppressors and poly-ADP ribose polymerase (PARP) inhibitors [12] (see Figure 1). Several approaches to obtain 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one derivatives of type 1 are known in the

α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

• Scott Benz and
• Andrew S. Murkin

Beilstein J. Org. Chem. 2021, 17, 2570–2584, doi:10.3762/bjoc.17.172

• from the above work from the Gademann group, Kalmode et al. incorporated the same synthetic strategy into their total synthesis of racemic periconianone A [12]. Interestingly, these authors not only tested the natural product for neural anti-inflammatory activity but also the two immediate synthetic

• other hand, is proposed to give rise to isolated products 94 (R = Me, Et), 95, and 96. Interestingly, 94 showed anti-inflammatory activity. α‑Iminol rearrangements Whereas α-ketol rearrangements must be driven thermodynamically by the presence of a destabilizing feature in the reactant (e.g., aldehyde

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• polyamidoamine (PAMAM) dendrimers have been shown to be effective for minimally invasive drug delivery [83]. The reinforced cryogels main function was to provide scaffolding for cell growth and also incorporated the anti-inflammatory corticosteroid drug betamethasone sodium phosphate (BSP) for delivery when

• water-soluble branched polysaccharide, isolated from kefir grains. Scaffolds were prepared by cryogelation of a 2% w/v aqueous solution of the kefiran, without the need for any crosslinking agents. Release of diclofenac, a non-steroidal anti-inflammatory drug, was low with 15% of the drug released after

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

• Robin Klintworth,
• Garreth L. Morgans,
• Stefania M. Scalzullo,
• Charles B. de Koning,
• Willem A. L. van Otterlo and
• Joseph P. Michael

Beilstein J. Org. Chem. 2021, 17, 2543–2552, doi:10.3762/bjoc.17.170

• nonsteroidal anti-inflammatory drug [6], and licofelone (7) [9][10], a promising co-drug for anticancer combination chemotherapy [7]. Related 5,6,7,8-tetrahydroindolizines such as CMV423 (8) [11], a lead compound for treating infections by human cytomegalovirus, and the natural products polygonatine A (9) [12

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

• Ren-Jie Fang,
• Chen Yan,
• Jing Sun,
• Ying Han and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2021, 17, 2425–2432, doi:10.3762/bjoc.17.159

• alkaloids and pharmacologically active compounds representing a broad spectrum of important bioactivities such as anticancer, antituberculosis, anti-protein kinase C, antipsychotic, and antioxidative activities [1][2][3][4][5]. For some examples, carprofen is a nonsteroidal anti-inflammatory pharmaceutical

Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

• Tülay Yıldız,
• İrem Baştaş and
• Hatice Başpınar Küçük

Beilstein J. Org. Chem. 2021, 17, 2203–2208, doi:10.3762/bjoc.17.142

• anticarcinogenic [1][2], antiviral [3], antibacterial [4][5], and anti-inflammatory [6]. Because of their pharmaceutical activity, they are used in photodynamic therapy [7][8][9]. In addition, they have an important place in the dye industry due to their photochemical and photophysical properties. They are also

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• , anthracene derivatives display useful biological activities; for instance, the anthraquinone derivatives 5 and 6 exert antimicrobial and anti-inflammatory activity, respectively (Figure 1) [15][16]. Despite some difficulties and limitations, a number of synthetic methods for preparing anthracene derivatives

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

• , it is present in compounds that have a significant anti-inflammatory activity (43 and 44) (Scheme 16A) [125]. The introduction of two distinct aryl moieties into arenes was also shown to be feasible through the sequential functionalization with two different Grignard reagents. For this purpose, the

• free amine derivative was produced in 43% overall yield. The 2,8-dioxabicyclo[3.3.1]nonane skeleton is contained in biflavonoids and was shown to exhibit many medicinal activities like antiviral, anti-inflammatory and antitumor properties. The bicyclic compound 49 was aminated at the benzylic position

• effects (85–89, Scheme 31A), such as antioxidant, α-amylase inhibitor, anticancer, and anti-inflammatory activities [164]. The reaction was promoted by non heme-Fe catalyst, behaving similarly to the bioinspired iron catalyst in a redox-selective way. The combination of Fe(phen)3(PF6)3 and tertiary

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• late-stage methylation of complex drug derivatives, such as of indoprofen (anti-inflammatory), tedizolid (antibiotic), and celecoxib (anti-inflammatory), successfully delivered methylated drug candidates 22f–h, respectively. In addition, methylation of proline-containing multipeptides was achieved via

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

• Thiago S. Silva and
• Fernando Coelho

Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112

• further demonstrated by the hydroalkylation of the anti-inflammatory drug phenylbutazone (7j). Gold(I)/gold(III) and silver(I) catalysis in olefin hydroalkylation The early limitations associated with Pd catalysis in olefin hydroalkylation reactions prompted the search for alternative metals for olefin

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati,
• Andhika B. Mahardhika,
• Lukas L. Wendt and
• Christa E. Müller

Beilstein J. Org. Chem. 2021, 17, 1464–1475, doi:10.3762/bjoc.17.102

• , and scalability to obtain gram amounts for biological studies. Selected compounds were found to display affinity for cannabinoid receptors, which are promising drug targets for the treatment of inflammatory and neurodegenerative diseases. Keywords: alkylation of indole; anti-inflammatory; binding

• biological activities (Figure 1) [10]. Unsubstituted DIM (I), for example, exhibits antimicrobial [5], anticancer [11][12][13], and anti-inflammatory effects (Figure 1) [14]. There is preclinical evidence for activity against several types of cancer [15], and DIM has been clinically evaluated for the

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98