Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• biologically active useful candidates. NSAIDs (non-steroidal anti-inflammatory drugs) currently approved like piroxicam [12], meloxicam [13], and other derivatives of these two are well known for their activities [5]. 1,2-Benzothiazines are highly bioactive moieties and have been explored as antibacterial [14

• autoimmune diseases [18], osteoarthritis [29], hemorrhage [25], and cardiac diseases [30]. Pyrazole moieties have a wide spectrum of pharmacological efficiencies. One known example is celecoxib®, a clinically used anti-inflammatory and COX-2 enzyme-inhibiting drug [31]. In some cases, inclusion of a pyrazole

• [9]. Pyrazolobenzothiazines have also been synthesized and explored as p38α MAPK inhibitors [35]. In 2015, Sabatini and co-workers synthesized a novel series of pyrazolobenzothiazines and identified as new generation anti-inflammatory agents. Two of these compounds are reported with an IC50 of 0.5 µM

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• representative studies include antibacterial, anti-inflammatory, antioxidant, selective inhibitor of COX-2 [34], and anti-HIV activity [35]. In this context, even though indole is considered a privileged scaffold present in some anticancer agents [36], a few examples of methanesulfonylindoles are studied as

• cytotoxic compounds. For example, a cytotoxic effect was found in CAL 27 cells, presumably through a mechanism of TNF-α inhibition in vitro, which could be related to the anti-inflammatory effect identified in several studies of NSAIDs that inhibit cancer cell viability in vitro [37][38]. In another study

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• abilities has been verified by mathematical calculations. Keywords: decarbonylation–oxidation; hydroperoxide; 2-hydroxybenzophenone; transition-metal-free; UV-protection; Introduction Benzophenone compounds are ubiquitous in nature, and show biological activities such as anti-inflammatory, antiviral, and

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

• are widely used in pharmacology due to their pronounced biological activities and low toxicities. The introduction of a hydroxy function into uracil and pyridine molecules has led to compounds with antioxidant, anti-inflammatory, and immunomodulatory activity (3-hydroxy-6-methyl-2-ethylpyridine, 5

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• heteroarylations [75]. For example, the heteroarylations of the nonsteroidal anti-inflammatory drug pranoprofen was accomplished, producing the desired product in 67% yield only within 30 min (Scheme 51). The f-EPC system integrates the advantages of electrophotocatalysis and flow chemistry, providing a rapid and

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

• , anticancer, non-steroidal anti-inflammatory, antihypertensive, antipsychotic, anxiolytic and in other pharmaceuticals [3][4][5]. Therefore, considering the diversity of biological properties, development of reliable approaches for the synthesis of new nitrogen heterocyclic systems is a highly urgent goal

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

• Deepa Nair,
• Abhishek Tiwari,
• Banamali Laha and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

• properties such as anticancer, anti-HIV protease, anti-ageing, anti-inflammatory and anti-oxidant, to name a few [12][13][14][15][16][17][18][19][20][21][22][23]. Considering the fact that curcumin’s uniqueness is associated with its ability to function as a multifunctional substrate in various organic

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• wide range of pharmacological activities, such as anti-inflammatory, anti-arrhythmic, antitumor, antifungal, antibacterial, and anti-HIV activities [7][8][9][10][11][12][13]. For example, two N1-substituted bioactive indazoles are found in Figure 1, danicopan (1), a complement factor D inhibitor for

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

• of Th1 cytokine, leukotriene and chemokines release, or IL-6 induction. Histamine targets histamine receptors H1–4, triggering pro-inflammatory or anti-inflammatory events depending on the receptor type and cells involved [45][49]. Histamine also plays a critical role in both vertebrates and

• thiohistidine (89) were evaluated for skincare anti-inflammatory properties by Brancaccio et al. (Scheme 12) [64]. These compounds, biosynthesized by microalgae, bacteria and marine invertebrates feature skin protection via Nrf2 activation (nuclear factor erythroid 2-related factor 2). Antimalarial properties

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

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

• 30 were obtained in moderate yields (ranging from 29% to 50%, Scheme 9) and were tested as anti-inflammatory drugs in RAW 264.7 cells and as inhibitors of rat ear edema. Unfortunately, the tested compounds exhibited weak activity in all assays. Khripach et al. reported a three-step sequence for the

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• resulting natural products with a spectrum of chemical complexity, contributing to the broad range of biological activities exhibited by RiPPs. Bioactivities attributed to RiPPs include a wide range of effects, such as antibiotic, antifungal, antiviral, antiparasitic, antitumour, analgesic, anti

• -inflammatory, antidiabetic, antihypertensive, and anti-parkinsonian [7][8]. This diverse profile makes RiPPs particularly valuable for various therapeutic and medicinal applications. Generally, peptide natural products are promising drug development candidates due to their intermediate molecular weight, which

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl₂ and NH₄SCN/KSeCN

• Jialiang Wu,
• Haofeng Shi,
• Xuemin Li,
• Jiaxin He,
• Chen Zhang,
• Fengxia Sun and
• Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

• used as an effective anti-inflammatory pharmaceutical [23]. On the other hand, organic thiocyanates usually serve as useful synthetic intermediates that can be conveniently converted to sulfur-containing derivatives including sulfides [24], disulfides [25], thiocarbamates [26], and trifluoromethyl

• ; thiocyanation; thiocyanogen chloride; Introduction Pyrazoles and their derivatives are an important class of five-membered heterocyclic compounds [1][2][3][4][5] that have drawn increasing attention from organic chemists, due to their potential biological and pharmaceutical properties including anti

• -inflammatory [6], antiviral [7], antibacterial [8], antifungal [9], cytotoxic [10], antioxidant [11], and analgesic [12] activities. For instance, celecoxib (I, Figure 1) (for treating rheumatoid arthritis and osteoarthritis), tepoxalin (II, Figure 1) (a veterinary painkiller used to relieve pain from muscle

One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• can be found in natural products and synthetic compounds with antitumor, anti-HIV, antibiotic, antifungal, antivirus, and anti-inflammatory activities [18][19][20][21]. The antischistosomal drug praziquantel (PZQ), a tetrahydroisoquinoline derivative, is a commercialized drug for the treatment of

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

• 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

• diseases, epilepsy, convulsion, and insomnia) and cardiovascular diseases (hypertension, hyperlipidemia, and atherosclerosis). In addition, they also have anticancer, anti-inflammatory, antioxidative, liver- and kidney-protective, antidepressant, and antidiabetic properties (Figure 2). Neuroprotection

• Chinese Medicine, No. 10 Poyang Lake Road, Tuanbo New Town, Jinghai District, Tianjin 301617, China 10.3762/bjoc.20.68 Abstract Crocins are water-soluble apocarotenoids isolated from the flowers of crocus and gardenia. They exhibit various pharmacological effects, including neuroprotection, anti

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• activities, such as antiviral [1], anticonvulsant [2], antibacterial [3], antipyretic [4], antituberculosis [5], anticancer [6], anthelmintic [5], antifungal [7], analgesic [8], antiulcer [9], antiprotozoal [10], antitumor [11], and anti-inflammatory [12]. Examples of commercial drugs are depicted in Figure

•  1 [13] and include alpidem (anxiety disorders), minodronic acid (osteoporosis), miroprofen (non-steroidal anti-inflammatory drug, NSAID), necopidem (insomnia), olprinone (acute heart failure), saripidem (type A GABA receptor agonist), zolimidine (gastroesophageal reflux disease), and zolpidem

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• polyketides, alkaloids, sterol derivatives, terpenoids, and macrolides, with polyketides and alkaloids comprising 40% and 32% of the total, respectively. Alkaloids are a diverse group of compounds with multiple pharmacological activities, including anti-inflammatory, antibacterial, antiviral, insecticidal

Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides

• Alexander Yanovich,
• Anastasia Vepreva,
• Ksenia Malkova,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48

• products. For example, spirocyclic Δα,β-butenolides (furan-2(5H)-ones) represent a valuable class of molecular frameworks for drug design and are abundant in nature [15]. Bioactive naturally occurring spiro Δα,β-butenolides include spirofragilide (with anti-inflammatory, antibiotic, antitumor, anti-HIV

• including aldosterone receptor antagonistic [22], anti-inflammatory [23], and anti-HIV [24] activity. Substantial drugs based on spirocyclic tetrahydrofuran and pyran moieties include spironolactone (a multi-target drug that is primarily used to treat high blood pressure and heart failure) [25

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• and fungi at 20 µg per disc in the paper disc diffusion method. Dihydroxybenzoic acid (DHBA) plays a role in anti-inflammatory, antihyperglycemic, antiapoptotic, and antioxidant processes [14]. 2,3-DHBA is found in nature and is produced by various plants (e.g., Gentiana rigerscense and Vinca minor

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• our attention. Several meroterpenoids, alkaloids, polyketides, and sesquiterpenoids from the species displayed various biological properties including anti-inflammatory, antimicrobial, and cytotoxic activities [7][8][9]. In the present work, two rare new examples of sulfur-containing ovalicin

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• cruciferous vegetables, as hydrolysis products from the metabolism of glucosinolates [1]. In 2017, Müller and her research team showcased the ability of BIMs to operate as anti-inflammatory drugs by acting as GPR84 agonists [2]. GPR84 is a protein-coupled receptor found in immune cells, which regulates a

• clinical trials as neuroprotective agents, presenting an attractive alternative to traditional anti-inflammatory and anti-Parkinson’s disease drugs [7]. With the increased drug resistance of bacteria to modern medicine, BIMs have emerged as an interesting alternative, due to their antibacterial and

• (indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• and its derivatives are widely distributed in nature in microorganisms and fungi, and they represent the key structural units of many important drugs with antibacterial, antifungal, anticancer, anti-inflammatory, and antiviral activities [1][2]. Due to the presence of several reactive centers in the

Synthesis of spiropyridazine-benzosultams by the [4 + 2] annulation reaction of 3-substituted benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes

• Wenqing Hao,
• Long Wang,
• Jinlei Zhang,
• Dawei Teng and
• Guorui Cao

Beilstein J. Org. Chem. 2024, 20, 280–286, doi:10.3762/bjoc.20.29

• field [4][5][6]. Pyridazine drugs have also shown high pharmaceutical activity. Many types of pyridazine drugs have been listed for antibacterial, anti-inflammatory, and other purposes [7][8][9][10]. Nowadays, a range of transformations to spirobenzosultams have been established using N-sulfonyl

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• and used in medicine, food industry, catalysts, dyes, functional materials, oil refining, and electronics [1][2]. Quinoline and its derivatives have antibiotic, antimalarial, antitumor, anti-inflammatory, antihypertensive, and antiretroviral properties [3][4]. Therefore, at present, there is a need

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