Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-addition/aldol reaction followed by RCM/syn-dihydroxylation

• Michał Malik and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2016, 12, 2602–2608, doi:10.3762/bjoc.12.255

• to their similarity to carbohydrates, these compounds often possess interesting biological properties, e.g., they may act as glycosidase inhibitors [2][3][4]. One of such compounds, acarbose [5][6][7], found an application as a drug and is marketed worldwide. Five- and six-membered cyclitols are a

• well-known and recognizable group of carbasugars. The synthesis of these monocyclic compounds (such as 1 and 2, Figure 1) and evaluation of their biological properties remain a challenging and vital research area [8][9][10][11]. On the other hand, bicyclic analogs of cyclitols are not as well

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• chemical synthesis and investigation of their physicochemical and biological properties (early works are reviewed in [1][2]). Studies on thioxo- and azapyrimidine nucleosides are an inspiring subject of investigation due to their very special biochemical [3][4][5][6][7] and biophysical properties in

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

• Florin Albota,
• Mino R. Caira,
• Constantin Draghici,
• Florea Dumitrascu and
• Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

• its derivatives exhibit remarkable biological activities and optical properties. Indolizine is a privileged structure for the design of new drugs and its framework is present in many natural compounds. As a consequence, the synthesis, chemical, physicochemical and biological properties of indolizines

• have been the subject of various reviews [6][7][8][9][10][11][12][13][14][15]. Sydnones 3 are mesoionic heterocyclic compounds with a 1,2,3-oxadiazole skeleton and their chemistry and biological properties are well represented and documented in the literature [20][21][22][23][24][25][26]. The most

Towards potential nanoparticle contrast agents: Synthesis of new functionalized PEG bisphosphonates

• Souad Kachbi-Khelfallah,
• Maelle Monteil,
• Margery Cortes-Clerget,
• Evelyne Migianu-Griffoni,
• Jean-Luc Pirat,
• Olivier Gager,
• Julia Deschamp and
• Marc Lecouvey

Beilstein J. Org. Chem. 2016, 12, 1366–1371, doi:10.3762/bjoc.12.130

• stability. To overcome this main drawback, the NP surface could be derivatized by various functional groups. These ligands have to possess certain chemical and biological properties as the flexibility, the hydrophilicity and an absence of in vivo toxicity. In addition, the nanoparticulate systems so

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• presented in Table 1, it can be concluded that the type of functional group has a large influence on the biological properties of the tested compounds. These results indicate that the presence of a methylphenyl group causes a compound to be toxic for normal lymphocytes (3Ac and 3Ai); a similar phenomenon

• ). Although, dimethyl N-(4-methylphenyl)amino(pyren-1-yl)methylphosphonate 4c demonstrated important cytotoxicity (IC50 ≈ 15 μM) for both cancer cell lines, it was unfortunately found to be toxic towards normal lymphocytes (IC50 ≈ 17 μM). More profound studies on biological properties of selected compounds

• phosphonic analogues of phenylglycine, exhibited their herbicidal activity [10], and are used as plant growth regulators [10], agrochemical fungicides [11][12] and glutamate receptor modulators [13]. It is therefore expectable that C-pyrene derivatives may have similar or even more promising biological

Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji–Trost coupling

• Sebastian Bretzke,
• Stephan Scheeff,
• Felicitas Vollmeyer,
• Friederike Eberhagen,
• Frank Rominger and
• Dirk Menche

Beilstein J. Org. Chem. 2016, 12, 1111–1121, doi:10.3762/bjoc.12.107

• ), their unique architecture is characterized by an ester-linked bromopyrrole carboxylic acid and a tetrahydropyrimidine ring in which one of the amino groups is attached to a quaternary carbon center. Due to their intriguing structures in combination with the promising biological properties this class of

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

• -substituted flavonoids 5d–m. In order to investigate the influence of halogen substituents on the biological properties of tricyclic flavonoids, we first synthesized flavonoid 5m (R1 = R3 = H) having no halogen substituents in the structure as a reference compound. The MIC and MBC values obtained for this

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• , gave the desired 5'-deoxy muraymycin C4 (65) (Scheme 9) [78]. In addition to the described synthetic routes, a range of other muraymycin analogues has been prepared. In the interest of conciseness, this synthetic work is not discussed here, but the biological properties of such analogues will be

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

• Guozheng Huang,
• Simon Schramm,
• Jörg Heilmann,
• David Biedermann,
• Vladimír Křen and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

• isosilibinin (3), silychristin (5), silydianin (11), and dehydrosilibinin [1][5]. Natural and commercially available silibinin is the diastereomeric mixture (quasi equimolar) of silybin A (1a) and silybin B (1b). Because of the well-known biological properties of silibinin and the other compounds of the

• reaction. We investigated the reaction under Mitsunobu conditions using the latter sequence of addition [10] for silibinin and benzoic acid, or 2,2-dimethyl-3-(nitrooxy)propanoic acid (7, Scheme 1), an NO-donor compound with several biological properties, e.g., vasorelaxation [27]. Compound 7 had initially

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• -alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol

• in the diagnosis of breast cancer with this imaging technique [33][34]. Considering the synthetic and biological importance of inositol analogues, the design of new inositol derivatives to study their biological properties and to understand their binding mechanisms with molecular targets, for

• . Noteworthy aspects of this methodology are the easy accessibility of different types of arms in term of configuration (myo and scyllo), linking method and length, which could modulate the biological properties. The series bearing an arm terminated by a hydroxy group could provide interesting candidates for

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• amino acid residues, and they exhibit a wide range of interesting biological properties, such as insecticidal, cytotoxic, and moderate antibiotic activity [128]. The secretion of destruxins is weakly correlated to fungal virulence and insecticidal activity, because injection, ingestion or topical

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

• beneficial biological properties, i.e., free radical scavenging activity [3], cardioprotective action [4], antibacterial and antiviral activities [5]. Two flavonoids in the class of flavanones, hesperetin and naringenin (chemical structures in Figure 1), can be extracted from citrus fruits such as lemon

Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp²)–H bond arylations

• Fatiha Abdelmalek,
• Fazia Derridj,
• Safia Djebbar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2015, 11, 2012–2020, doi:10.3762/bjoc.11.218

• dramatically influence both chemical properties and reactivities owing to its electronegativity, size, lipophilicity, and electrostatic interactions. For example, introduction of fluorine into natural products can result in beneficial biological properties [6]. On the other hand, fluorinated π-conjugated

A new method for the synthesis of α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues

• Anna Kuźnik,
• Roman Mazurkiewicz,
• Mirosława Grymel,
• Katarzyna Zielińska,
• Jakub Adamek,
• Ewa Chmielewska,
• Marta Bochno and
• Sonia Kubica

Beilstein J. Org. Chem. 2015, 11, 1418–1424, doi:10.3762/bjoc.11.153

• acid phosphorus analogues; electrochemical α-methoxylation; 1-phosphinoylalkylphosphonate; 1-phosphinylalkylphosphonate; Introduction α-Aminophosphonic and α-aminophosphinic acids, as phosphorus analogues and bioisosters of α-amino acids, exhibit a variety of important biological properties [1][2][3

Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes

• Ivan Šnajdr,
• Kamil Parkan,
• Filip Hessler and
• Martin Kotora

Beilstein J. Org. Chem. 2015, 11, 1392–1397, doi:10.3762/bjoc.11.150

• ; catalysis; carbohydrates; cross-metathesis; ruthenium; Introduction Natural and unnatural C-substituted glycosides are important compounds with a plethora of attractive biological properties and they often have been used as artificial DNA components [1]. Among various synthetic procedures providing C

Synthesis and evaluation of the biostability and cell compatibility of novel conjugates of nucleobase, peptidic epitope, and saccharide

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum,
• Khalid Omar Al Footy,
• Khadija Omar Badahdah and
• Bing Xu

Beilstein J. Org. Chem. 2015, 11, 1352–1359, doi:10.3762/bjoc.11.145

• evaluate their physiochemical and biological properties. Based on the above rationale, we chose two short peptidic epitopes, TTPV and LGFNI, from two well-characterized proteins as the building blocks for nucleopeptides [9][10][11][12][13] or NAS conjugates. TTPV is from a calcium channel protein

Radical-mediated dehydrative preparation of cyclic imides using (NH₄)₂S₂O₈–DMSO: application to the synthesis of vernakalant

• Dnyaneshwar N. Garad,
• Subhash D. Tanpure and
• Santosh B. Mhaske

Beilstein J. Org. Chem. 2015, 11, 1008–1016, doi:10.3762/bjoc.11.113

• such as lurasidone, phensuximide, buspirone, (R/S)-thalidomide, lenalidomide and apremilast contain cyclic imide moieties and possess a wide range of biological properties (Figure 1) [13][14][15][16][17]. Cyclic imides have found immense applications in agrochemicals such as chlorophthalim (herbicide

A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles

• Roman A. Irgashev,
• Arseny A. Karmatsky,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2015, 11, 1000–1007, doi:10.3762/bjoc.11.112

• attention of researchers, mainly due to the fact that thieno[2,3-b]indole derivatives exhibit a wide range of biological properties, and can be regarded as promising compounds for agricultural or pharmacological applications. For example, the alkaloid thienodolin [1], isolated from the fermentation mixture

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

• Roberto Romeo,
• Caterina Carnovale,
• Salvatore V. Giofrè,
• Maria A. Chiacchio,
• Adriana Garozzo,
• Emanuele Amata,
• Giovanni Romeo and
• Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

• lead to interesting biological properties, we report in this paper the preparation of a small library of nucleoside analogues 7 (Figure 2), where the furanose ring is substituted by an isoxazolidine system and a triazole unit replaces the phosphodiester linker at 5’ position of the 2’-oxa-3’-aza-4’a

Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts

• Bin Yin,
• Shinsuke Inagi and
• Toshio Fuchigami

Beilstein J. Org. Chem. 2015, 11, 85–91, doi:10.3762/bjoc.11.12

• fluorine atom(s) into organic molecules very often improves or enhances their desired characteristic physical and biological properties hence organofluorine compounds are highly useful for medicinal, agrochemical, and materials science [1][2][3][4][5][6]. In order to prepare new fluorine compounds

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

• Pavel K. Mykhailiuk

Beilstein J. Org. Chem. 2015, 11, 16–24, doi:10.3762/bjoc.11.3

• physicochemical and biological properties [1][2][3][4][5][6][7][8]. It is not surprising, therefore, that up to 20% of all modern drugs contain at least one fluorine atom [9][10][11]. Fluorinated pyrazoles, for example, do play a role in medicinal chemistry: among them are inhibitors of the measles virus RNA

A carbohydrate approach for the formal total synthesis of (−)-aspergillide C

• Pabbaraja Srihari,
• Namballa Hari Krishna,
• Ydhyam Sridhar and
• Ahmed Kamal

Beilstein J. Org. Chem. 2014, 10, 3122–3126, doi:10.3762/bjoc.10.329

• , 71.0, and 2.0 μg/mL, respectively [5][6]. The striking structural architecture and interesting biological properties have attracted significant attention from synthetic chemists with respect to their total synthesis [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] and have

New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones

• Emilian Georgescu,
• Alina Nicolescu,
• Florentina Georgescu,
• Florina Teodorescu,
• Daniela Marinescu,
• Ana-Maria Macsim and
• Calin Deleanu

Beilstein J. Org. Chem. 2014, 10, 2377–2387, doi:10.3762/bjoc.10.248

• imidazole ring, alkyl bromoacetates and non-symmetrical electron-deficient alkynes in the molar ratio 1:2:1, in 1,2-epoxybutane, enabling thus the expansion of studies on the biological properties of these compounds. Experimental General. Melting points were measured on a Boëtius hot plate microscope and

A new approach for the synthesis of bisindoles through AgOTf as catalyst

• Jorge Beltrá,
• M. Concepción Gimeno and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2014, 10, 2206–2214, doi:10.3762/bjoc.10.228

• bisindolylmethane derivatives (BIMs), many of them isolated from marine natural sources [15][16] and are an important class of indole derivatives which exhibit an appealing range of biological properties such as antibacterial, antifungal, antimicrobial or anti-inflammatory, among others (Figure 1) [17

• interesting biological properties, the development of new efficient, general and eco-friendly protocols using benign catalytic systems with structurally different aldehydes and easy accessible catalysts still remains a continuous demand. Among the variety of Lewis acids employed in this reaction such as In

Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds

• Miroslav Palík,
• Jozef Kožíšek,
• Peter Koóš and
• Tibor Gracza

Beilstein J. Org. Chem. 2014, 10, 2077–2086, doi:10.3762/bjoc.10.216

• sizes are found in many different biologically active compounds. Particularly, substituted tetrahydrofuran units are present in a large branch of natural products that display interesting biological properties, such as goniofufurone 1 [1], goniothalesdiol 2 [2], varitriol 3 [3], erythroskyrine 4 [4][5