Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• triglyceride serum levels, this CD reduces cholesterol accumulation in atherosclerotic plaques by the modification of HDL-cholesterol levels. It is noteworthy that HDL and apolipoprotein A-I (ApoA-I) cause a dose-dependent reduction in the activation of CD11b (i.e., anti-inflammatory effect on monocytes

• , the researchers suspect that the CD boosts the activity of macrophages, enabling them to attack excess cholesterol without causing inflammation. Indeed, CD increases liver X receptor (LXR) involved in the antiatherosclerotic and anti-inflammatory effects as well as in the RCT improvement. Moreover, α

Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides

• Ilya V. Efimov,
• Marsel Z. Shafikov,
• Nikolai A. Beliaev,
• Natalia N. Volkova,
• Tetyana V. Beryozkina,
• Wim Dehaen,
• Zhijin Fan,
• Viktoria V. Grishko,
• Gert Lubec,
• Pavel A. Slepukhin and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2016, 12, 2390–2401, doi:10.3762/bjoc.12.233

• chemistry over the years [1]. Isoxazoles have been found in natural products [1], and they exhibit anticancer [2], antiviral [1], anti-inflammatory [3], antidiabetic [4], anti-Alzheimer [5] and many other types of biological activity [6]. Isoxazolines and isoxazoles have been applied as chemosensors, liquid

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• activities, including antibacterial, antiviral, antifungal, anti-allergic, anti-oxidant, and anti-inflammatory [348][349]. The treatment of endoperoxide 238 with Et3N gave 1,4-diketone 240 in quantitative yield instead of expected hydroxy ketone 239 (Scheme 73) [350][351][352]. The endoperoxide 238 is

• rearrangement is one of the steps in the synthesis of the natural compound angelone from Nauclea, a plant species widely acclaimed for its anti-inflammatory and antibacterial utilities in traditional Chinese herbal medical formulations [370]. A Kornblum–DeLaMare enantiomeric resolution was also used to obtain

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

• Bo Yang,
• Chuanye Tao,
• Taofeng Shao,
• Jianxian Gong and
• Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

• broad range of biological activities such as antibacterial [11][12][13], antiviral [14][15], anti-inflammatory [16][17], antitumor [18][19][20], and anti-HIV [21]. It is found as the core structure in several drugs such as Zolpidem, Alpidem and Zolimidine (approved for treatments of insomnia, anxiety

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• , carbamate 138, hexahydrobenzothiophene 140 and benzothiophene 142 were converted to the corresponding bisphosphonates 139, 141 and 143, respectively (Scheme 30). The synthesized heterocyclic bisphosphonates showed anti-inflammatory properties. 3 Knoevenagel-induced domino reactions An efficient method into

Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• :36.5 to 67.5:32.5 er). To demonstrate the utility of the transformation, the sulfur–carbon bond of 26a was reduced using Raney nickel to access (S)-naproxen (27), an anti-inflammatory drug (Scheme 6b). Inspired by the work of Pracejus, Tan and colleagues applied their C2-symmetric guanidine catalyst 30

Biradical vs singlet oxygen photogeneration in suprofen–cholesterol systems

• Fabrizio Palumbo,
• Francisco Bosca,
• Isabel M. Morera,
• Inmaculada Andreu and
• Miguel A. Miranda

Beilstein J. Org. Chem. 2016, 12, 1196–1202, doi:10.3762/bjoc.12.115

• nonsteroidal anti-inflammatory drug that contains the 2-benzoylthiophene (BZT) chromophore and has a π,π* lowest triplet excited state. In the present work, dyads (S)- and (R)-SP-α-Ch (1 and 2), as well as (S)-SP-β-Ch (3) have been prepared from β- or α-Ch and SP to investigate the possible competition between

• light. The latter involves energy transfer from the photosensitizer triplet excited state to ground state molecular oxygen [5][6]. Ketoprofen (KP) is a nonsteroidal anti-inflammatory drug that contains the benzophenone (BZP, Figure 1) chromophore and displays a n,π triplet excited state [7][8][9

• -Ch dyads are suitable to generate biradicals by intramolecular HA from the C7-allyl position of Ch [11][12], whereas the TPA-α-Ch analogs are unreactive via HA but they generate singlet oxygen efficiently [13]. Suprofen (SP) is another nonsteroidal anti-inflammatory drug, which contains a BZT

Antibacterial structure–activity relationship studies of several tricyclic sulfur-containing flavonoids

• Lucian G. Bahrin,
• Henning Hopf,
• Peter G. Jones,
• Laura G. Sarbu,
• Cornelia Babii,
• Alina C. Mihai,
• Marius Stefan and
• Lucian M. Birsa

Beilstein J. Org. Chem. 2016, 12, 1065–1071, doi:10.3762/bjoc.12.100

• display antibacterial, antiviral, antifungal, anti-inflammatory and anticancer properties [4][5][6][7][8][9][10]. Their polyphenolic structure also gives them excellent anti-oxidant and cardioprotective properties [11][12]. Our research group has recently reported the antibacterial properties of a new

The synthesis of functionalized bridged polycycles via C–H bond insertion

• Jiun-Le Shih,
• Po-An Chen and
• Jeremy A. May

Beilstein J. Org. Chem. 2016, 12, 985–999, doi:10.3762/bjoc.12.97

• remote functionalizations on the piperidine ring. Many examples of the sequence with different piperidines were also reported. The resulting 3-amino-2,6-disubstituted piperidines like 52 are known to display anti-allergic and anti-inflammatory activities. Rao generated a bridged polycycle via a formal C

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• its leaves presents anti-inflammatory properties. Cyperane, guaiane, nortrixane, and trixane sesquiterpene types were reported as the main metabolites in Jungia species. This work aims to describe the isolation and identification of sesquiterpenes in the leaves of J. sellowii using liquid–liquid

• -inflammatory and antioxidant effects of J. paniculata were associated to the presence of flavonoids and other polyphenols [4]. Recently, we reported the in vivo anti-inflammatory properties of an aqueous fraction of the leaves of J. sellowii, that is in agreement with its popular use in Brazil [5]. Apart from

• herbs, widely distributed from Central to South America, including Southern Brazil. Species such as J. paniculata and J. polita are used in South America to disinfect and cure external wounds, to treat inflammation [1][2], and as a blood depurative [3]. Pharmacological studies demonstrated that the anti

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• ’-dichlorodihydrofluorescein (DCFH) to the fluorescent 2’,7’-dichlorofluorescein (DCF) [29]. This antioxidant activity was also linked to anti-inflammatory effects by testing the in vivo effects of 23 in a carrageenan-induced paw edema assay. Oral administration of 23 to mice prior to carrageenan injection resulted in a

• interesting target of research, due to the fact that the progression of Alzheimer’s disease was slowed down by using anti-inflammatory drugs. Thus, selective COX-2 inhibitors, anti-inflammatory compounds themselves, might have beneficial effects in vivo. Several derivatives of 6-alkyl (alkoxy or alkylthio)-4

Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins

• Joyeeta Roy,
• Tanushree Mal,
• Supriti Jana and
• Dipakranjan Mal

Beilstein J. Org. Chem. 2016, 12, 531–536, doi:10.3762/bjoc.12.52

• condensation; Hauser annulation; proisocrinins; Introduction Anthraquinones constitute the largest group of naturally occurring quinones [1][2][3][4][5]. Isolated mainly from fungal sources, they display a wide range of biological activities which include anti-inflammatory, antifungal, antiparasidal, and

A selective and mild glycosylation method of natural phenolic alcohols

• Mária Mastihubová and
• Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

• -glucopyranoside (vanillyl β-D-glucoside, 1) isolated from the exocarp of Juglans mandshurica Maxim showed antibacterial activity [1]. A wide range of pharmacological effects, e.g., anti-oxidant, anti-inflammatory, anticancer, hepatoprotective, cardioprotective, neuroprotective, antidiabetic, and antiviral

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• inclusion complexes. The data obtained by the dissolution method showed that complexation with RAMEB resulted in a better release of both flavanones to aqueous solution. The flavanones-β-CD/DM-β-CD complexes demonstrated a similar or a slight increase in anti-inflammatory activity and cytotoxicity towards

• , grapefruit and orange. Several reports on biological effects of hesperetin and naringenin have been found [6], including blood lipid- and cholesterol-lowering effects [7][8][9], anti-inflammatory [10][11][12][13] and anticancer [14][15][16] activities, improved microcirculation, recovery of venous ulcers

• dissolution study of flavanones were studied. The formed inclusion complexes were analyzed by DSC. The anti-inflammatory activity of inclusion complexes and the free flavanones were determined by investigating the secretion of certain cytokines in lipopolysaccharide (LPS)-stimulated macrophages. In addition

A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

• Xinlong Pang,
• Chao Chen,
• Ming Li and
• Chanjuan Xi

Beilstein J. Org. Chem. 2015, 11, 2365–2369, doi:10.3762/bjoc.11.258

• ]quinazolines were intensively investigated and promising biological activities were observed, such as anticancer, antiviral, antimicrobial, anti-inflammatory and anticonvulsant [3][4][5]. Indeed, some of them are already used as antimicrobial agents and lipid peroxidation inhibitors [6]. Consequently, the

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) – precursors for dyes and drugs

• Enas M. Malik,
• Younis Baqi and
• Christa E. Müller

Beilstein J. Org. Chem. 2015, 11, 2326–2333, doi:10.3762/bjoc.11.253

• ][18][19]. AQ derivatives can also exert a variety of pharmacological activities including laxative, anti-inflammatory [20][21], antitumor [22][23], antifungal [24], antiviral [25], and blood platelet inhibitory effects [26][27][28]. Reactive Blue 2 (RB-2), a chlorotriazinyl-containing AQ dye, defined

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

• Mingxing Liu,
• Jiarong Li,
• Hongxin Chai,
• Kai Zhang,
• Deli Yang,
• Qi Zhang and
• Daxin Shi

Beilstein J. Org. Chem. 2015, 11, 2125–2131, doi:10.3762/bjoc.11.229

• important because of their biological activity [1][2][3][4][5][6]. They have shown a wide range of pharmacological potential such as kinase inhibitors [1], antitumor [7][8], anti-inflammatory [9][10], antimicrobial [11][12][13], pesticides [14], radio protectant [15] and cardiovascular activity [16][17

Fe(II)/Et₃N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives

• Ekaterina E. Galenko,
• Olesya A. Tomashenko,
• Alexander F. Khlebnikov,
• Mikhail S. Novikov and
• Taras L. Panikorovskii

Beilstein J. Org. Chem. 2015, 11, 1732–1740, doi:10.3762/bjoc.11.189

• -imidazole polyamides [1][2][3][4][5]. Derivatives of 4-imidazolylpyrrole-2-carboxylic acid are much less known, though some of these compounds showed various bioactivities [6][7][8][9] and were patented as inhibitors of c-Met protein kinase [8] and as anti-inflammatory agents [9]. Additionally, 5

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

• Sundaravel Vivek Kumar,
• Shanmugam Muthusubramanian,
• J. Carlos Menéndez and
• Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

• examples are the neuroleptic olanzapine [3], the 2A3BT family of allosteric modulators of the A1 adenosine receptor, derived from 2-amino-3-benzoylthiophene and compounds such as PD-81,723 and T-62 [4], the non-steroidal anti-inflammatory tinoridine [5] and ranelic acid, whose strontium salt is used as a

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

• Ana Čikoš,
• Irena Ćaleta,
• Dinko Žiher,
• Mark B. Vine,
• Ivaylo J. Elenkov,
• Marko Dukši,
• Dubravka Gembarovski,
• Marina Ilijaš,
• Snježana Dragojević,
• Ivica Malnar and
• Sulejman Alihodžić

Beilstein J. Org. Chem. 2015, 11, 1447–1457, doi:10.3762/bjoc.11.157

• investigations have shown that beside their antibacterial activity, some macrolides exhibit anti-inflammatory/immunomodulatory [5][6][7][8][9][10], antitumor [11][12][13], antiviral [10] or antimalarial [14][15] activity. These discoveries have sparked a new interest in the structural modification of macrolides

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• ] including anti-oxidative [35], antihypertensive [36], anti-inflammatory [37] and antiplatelet agents [38]. They have also been used as fluorophores and exhibited good fluorescence properties when attached to a triazole ring [39][40]. Owing to the biological significance of porphyrins, 1,2,3-triazoles and

Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

• Qinggang Mei,
• Chun Wang,
• Zhigang Zhao,
• Weicheng Yuan and
• Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 1220–1225, doi:10.3762/bjoc.11.135

• relative drug preparations [5]. Icariin, icariside I (2), and their aglycone, icaritin (3) (Figure 1), possess multiple biological activities, such as anti-oxidative [6], anti-inflammatory [7], anti-osteoporotic [8], anticancer [9], neuroprotective [10], angiogenesis stimulating [11], testosterone mimetic

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• group in 2013 details the flow synthesis of the anti-inflammatory agent fanetizole (87) [85], in which ammonia gas was fed into the inner tube, whilst the outer tube contains a solution of phenethylisothiocyanate (89) in DME. The tube-in-tube system was placed onto the cooling unit of a Polar Bear Plus

Reactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki–Heck cross-coupling reaction

• Jerzy Zakrzewski and
• Bogumiła Huras

Beilstein J. Org. Chem. 2015, 11, 1155–1162, doi:10.3762/bjoc.11.130

• recognized as active agents against tuberculosis and malaria [3][7], cardiovascular diseases [3], and cancer [4]. Cinnamates show depigmenting [4], antidiabetic, antihyperglycemic, anticholesterolemic, anti-inflammatory, hepatoprotective, CNS depressant, anxiolytic, and cytotoxic activity [7]. Cinnamate

Thiazole formation through a modified Gewald reaction

• Carl J. Mallia,
• Lukas Englert,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 875–883, doi:10.3762/bjoc.11.98

• number of therapeutic areas including anticancer, antifungal, antibacterial, anti-inflammatory and as antidepressants (Figure 1) [1]. Several protocols have already been described for the synthesis of substituted thiazoles and benzothiazoles [2][3][4][5][6][7][8][9][10][11]. The current first choice