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Search for "biological activity" in Full Text gives 468 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

The preparation and properties of 1,1-difluorocyclopropane derivatives

  • Kymbat S. Adekenova,
  • Peter B. Wyatt and
  • Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

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  • -difluorocyclopropanes. First, we discuss the synthetic routes to gem-fluorocyclopropane derivatives. Then, we review the chemical transformations, emphasizing ring-opening reactions. Finally, we survey the biological activity of significant molecules that possess the 1,1-difluorocyclopropane fragment in the structure
  • . It will examine the role of the fluorine substituents in both ring-forming and ring-opening reactions, as well as methods for obtaining difluorocyclopropanes as single enantiomers. Several examples are provided to highlight the biological importance of this class of compounds. Keywords: biological
  • activity; cyclopropanation; difluorocyclopropane derivatives; synthesis; Introduction The chemistry of cyclopropane derivatives is one of the most intensively developing fields of organic chemistry. In the past decade there have been made many investigations to develop new chemo-, regio- and
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Review
Published 26 Jan 2021

1,2,3-Triazoles as leaving groups in SNAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

  • Kārlis-Ēriks Kriķis,
  • Irina Novosjolova,
  • Anatoly Mishnev and
  • Māris Turks

Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

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  • . Keywords: Arbuzov reaction; 2,6-bistriazolylpurines; nucleophilic aromatic substitution; purinylphosphonates; Introduction Acyclic nucleoside phosphonates (ANPs) are an important compound class due to their biological activity profile [1][2][3][4][5][6]. Compounds bearing a phosphonate moiety in their N9
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Published 20 Jan 2021

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

  • Dimas J. P. Lima,
  • Antonio E. G. Santana,
  • Michael A. Birkett and
  • Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

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  • ), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the
  • yield of 17.2% from oxime 103. Conclusion The peculiar structural factors of homotropane alkaloids added to the intriguing biological activity exerted by ladybirds (as demonstrated in this review for A. bipunctata), besides the fact that the insect releases these substances in minimal quantities, make
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Review
Published 05 Jan 2021

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

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Letter
Published 17 Dec 2020

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions

  • Yumeng Liang,
  • Akihito Taya,
  • Zhengyu Zhao,
  • Norimichi Saito and
  • Norio Shibata

Beilstein J. Org. Chem. 2020, 16, 3052–3058, doi:10.3762/bjoc.16.254

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  • trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed. Keywords: acyl fluorides; deoxyfluorination; fluorine; solvent-free; trifluoromethyl group; Introduction Due to an impressively wide effect of fluorine on the biological activity, the insertion of fluorine atoms or
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Published 14 Dec 2020

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

  • Vladimir Ilkin,
  • Vera Berseneva,
  • Tetyana Beryozkina,
  • Tatiana Glukhareva,
  • Lidia Dianova,
  • Wim Dehaen,
  • Eugenia Seliverstova and
  • Vasiliy Bakulev

Beilstein J. Org. Chem. 2020, 16, 2937–2947, doi:10.3762/bjoc.16.243

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  • -arylamino-1,2,3-triazole-4-N-sulfonylcarbimidamides. 2,5-Dithiocarbamoylpyridine reacts with sulfonyl azides to form a pyridine bearing two sulfonyl amidine groups. Keywords: amidines; Dimroth rearrangement; isoxazoles; sulfonyl thiazoles; thioamides; 1,2,3-triazoles; Introduction The biological activity
  • (2020830), contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif. Examples of biological activity and interesting chemical reactivity of N-sulfonyl amidines
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Published 01 Dec 2020

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

  • Emese Gal,
  • Luiza Gaina,
  • Hermina Petkes,
  • Alexandra Pop,
  • Castelia Cristea,
  • Gabriel Barta,
  • Dan Cristian Vodnar and
  • Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

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  • -functionalization of the methyl 4-((cyanomethyl)amino)benzoate skeleton, while dissimilarity was introduced by the C-functionalization with distinctive phenothiazinyl (2c), ferrocenyl (2i), and phenyl (2l) units, respectively, each of the constituent structural units being susceptible of imparting biological
  • activity. The viability of Salmonella typhimurium TA98 and TA 100, respectively, was assessed by exposing the histidine dependent bacteria to compound 2c, 2i, and 2l, respectively, directly on minimal glucose agar plates in the presence or absence of the metabolic activation system S9. The number of
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Published 30 Nov 2020

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

  • Viola Kolaříková,
  • Markéta Rybáčková,
  • Martin Svoboda and
  • Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

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  • enantioselective enyne metathesis yielding chiral building blocks for compounds with potential biological activity, e.g., norsalvinorin or cacospongionolide B. Keywords: Diels–Alder reaction; enediyne; enyne metathesis; ring-closing metathesis; ruthenium precatalyst; Introduction Among the plethora of metathetic
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Published 13 Nov 2020

Vicinal difluorination as a C=C surrogate: an analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity

  • Yuvixza Lizarme-Salas,
  • Alexandra Daryl Ariawan,
  • Ranjala Ratnayake,
  • Hendrik Luesch,
  • Angela Finch and
  • Luke Hunter

Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216

Graphical Abstract
  • described for 1 led to no detectable decomposition (Figure 3, Supporting Information File 1). Biological activity and solubility The biological activities of piperine (1) and the analog 2 were compared using two different assays, namely the inhibition of either acetylcholinesterase (AChE) or β-secretase
  • NMR. The numbering scheme for NMR spins is given on structure 2a. Analog 2 has greater stability to UV light than does piperine (1). Biological activity of piperine (1) and derivative 2. (a) Inihbition of AChE by 1 (IC50 >1000 μM) and 2 (IC50 = 51.7 μM) and (b) inhibition of BACE-1 by 1 (IC50 = 59.2
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Published 28 Oct 2020

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

  • Julia N. Artsemyeva,
  • Ekaterina A. Remeeva,
  • Tatiana N. Buravskaya,
  • Irina D. Konstantinova,
  • Roman S. Esipov,
  • Anatoly I. Miroshnikov,
  • Natalia M. Litvinko and
  • Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

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  • Drug Administration (FDA, USA) in 2005 as an antileukemia drug [51][52][53][54][55][56]. KR belonging to a family of phytohormones [57], displays a broad spectrum of biological activity [58][59][60], and in the form of pro-tides revealed an interesting spectrum of activity against neurodegenerative
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Published 22 Oct 2020

Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

  • Ekaterina E. Stepanova,
  • Maksim V. Dmitriev and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193

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  • studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H
  • , inducing its attack on the carbonyl group bearing a higher partially positive charge (for partial charges comparison, see Supporting Information File 1). As we were most interested in the biological activity of BTAs 3, preliminary antimicrobial and toxicity assays of these compounds were carried out
  • fused to 1,4-benzothiazin-2-one moieties, which may be interesting for studies on biological activity, chemosensors, and fluorescence. The first approach is based on the reaction of furan-2,3-diones 5 with o-aminothiophenols 1 in acetonitrile. This approach gave less side products, but the yields of
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Published 21 Sep 2020

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

  • Shahboz Yakubov and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

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  • atoms, including drugs used to treat cancer, HIV, smallpox and malarial infections (Figure 1) [5][6]. Moreover, fluorine atoms and trifluoromethyl groups have dramatic effects on the biological activity of agrochemicals, such as herbicides, insecticides and fungicides, as reflected by a plethora of
  • of polymers for their applications as water-repellent, chemical-proof, lubricant and thermally- and electrically-insulating materials [24]. The importance of fluorine atoms in chemical crop protection agents is well-acknowledged because fluorine improves the biological activity and user safety
  • , Scheme 24), demonstrating the power of this method for LSF, especially given the biological activity and prevalence of steroids, such as cholesterol, progesterone and testosterone. Interestingly, under their conditions, 2-heptanone, 2-decanone and 2-dodecanone as the substrates gave in each case a
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Published 03 Sep 2020

Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction

  • Alexander N. Reznikov,
  • Dmitry S. Nikerov,
  • Anastasiya E. Sibiryakova,
  • Victor B. Rybakov,
  • Evgeniy V. Golovin and
  • Yuri N. Klimochkin

Beilstein J. Org. Chem. 2020, 16, 2073–2079, doi:10.3762/bjoc.16.174

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  • ; tetrahydropyranes; Introduction Сhiral phosphonates [1][2] and phosphoryl-substituted heterocycles [2][3][4] have received significant attention in recent years due to their wide range of biological activity. For example, SF-2312 (1) is a natural antibiotic – an enolase inhibitor produced by the actinomycete
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Published 25 Aug 2020

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

  • Ksenia I. Kaskevich,
  • Anastasia A. Babushkina,
  • Vladislav V. Gurzhiy,
  • Dmitrij M. Egorov,
  • Nataly I. Svintsitskaya and
  • Albina V. Dogadina

Beilstein J. Org. Chem. 2020, 16, 1947–1954, doi:10.3762/bjoc.16.161

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  • Thiazolopyrimidines, whose molecules includes both thiazole and pyrimidine rings, have a structural analogy with the antipsychotic drugs ritanserin and setoperone (Figure 1) [1][2][3]. To date, a wide spectrum of biological activity of thiazolopyrimidines has been determined: anticancer [4][5], antimicrobial [6][7
  • containing practically significant heteroaromatic rings and a biologically active and hydrolysis-resistant phosphonate group, as it has been reported that the combination of several pharmacophore fragments in one molecule can lead to a synergistic increase in biological activity or an additional variety of
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Published 10 Aug 2020

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

  • Xiaoyun Hu,
  • Jianxin Guo,
  • Cui Wang,
  • Rui Zhang and
  • Victor Borovkov

Beilstein J. Org. Chem. 2020, 16, 1875–1880, doi:10.3762/bjoc.16.155

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  • activities [7][8]. For example, (S)-monastrol is 15-fold more effective in the inhibition of Eg 5 ATPase than its enantiomer, (R)-monastrol [9]. As more reports on the enantiospecific biological activity of DMPMs came to light, the development of an efficient and reliable asymmetric synthesis of enantiopure
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Published 31 Jul 2020

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

  • Giovanni Picca,
  • Markus Probst,
  • Simon M. Langenegger,
  • Oleg Khorev,
  • Peter Bütikofer,
  • Anant K. Menon and
  • Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

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  • -mannose (the α-anomer also shows biological activity, but to a lesser extent) [13][14][15], a short-chain (citronellol) mimic of dolichol [1][2][13], and a functional tag. The latter may either be a chemically reactive group (in MPC-1) or a fluorescent reporter group (in MPC-2). MPC-1 bears a benzophenone
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Published 20 Jul 2020

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

  • Dalel El-Marrouki,
  • Sabrina Touchet,
  • Abderrahmen Abdelli,
  • Hédi M’Rabet,
  • Mohamed Lotfi Efrit and
  • Philippe C. Gros

Beilstein J. Org. Chem. 2020, 16, 1722–1731, doi:10.3762/bjoc.16.144

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  • chemistry projects for the rapid access to a wide range of variously substituted compounds for structure–activity relationship studies. The biological activity of the molecules is currently being studied. Examples of bioactive nitrogen-containing heterocycles (indole [9], indolone [10], and cinnoline [11
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Published 17 Jul 2020

Models of necessity

  • Timothy Clark and
  • Martin G. Hicks

Beilstein J. Org. Chem. 2020, 16, 1649–1661, doi:10.3762/bjoc.16.137

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  • be used in cheminformatics applications to derive structure–property relationships for partition properties or solubility or structure–activity relationships for biological activity. Note, however, that the non-physically-observable model properties such as net atomic charges [18][19][38][39] are
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Published 13 Jul 2020

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

  • Giacomo Mari,
  • Lucia De Crescentini,
  • Serena Benedetti,
  • Francesco Palma,
  • Stefania Santeusanio and
  • Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

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  • [37][38]. Unlike BER, there have been few studies that concern the biological properties of functionalized DHBER. Attracted by the potentiality of this latter compound, we have realized the preparation of new arylhydrazono-functionalized DHBERs that were tested in vitro for their biological activity
  • ; in particular, we focused our attention on their antiproliferative capacity, due to our previous research experiences on the anticancer properties of both natural and synthetic molecules [39][40][41][42]. A common strategy to increase the biological activity of a class of products can be the
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Published 06 Jul 2020

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

  • Carlos H. Escalante,
  • Eder I. Martínez-Mora,
  • Carlos Espinoza-Hicks,
  • Alejandro A. Camacho-Dávila,
  • Fernando R. Ramos-Morales,
  • Francisco Delgado and
  • Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

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  • (Scheme 6). Although the reactivity was much lower (10 days) compared to the cycloadditions with 2-vinylpyrroles 8a–h (7 days) (Table 2), the diastereoselectivity remained rather high and similar to derivatives 8g and 8h. Considering the significant biological activity of indoles, octahydropyrrolo[3,4-e
  • that are known to have varied and robust pharmacological activity, such as isoborreverine (1) [12], mitomycin A (2) [13] and chlorizidine A (3) [14]. The indole moiety is incorporated into their structure, which is important because it is a seminal heterocycle that exhibits a wide range of biological
  • activity [15][16] and great diversity as building block [17][18]. Among the tetracyclic scaffolds, isoindolo[2,1-a]indoles have attracted a particular interest from the synthetic point of view, either as the target or the motif for designing novel annulation methodologies [19][20][21]. Indeed, isoindole
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Published 17 Jun 2020

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

  • Abimelek Cortes-Pacheco,
  • María Adelina Jiménez-Arellanes,
  • Francisco José Palacios-Can,
  • José Antonio Valcarcel-Gamiño,
  • Rodrigo Said Razo-Hernández,
  • María del Carmen Juárez-Vázquez,
  • Adolfo López-Torres and
  • Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

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  • biological activity methodology, computational details, and NMR/HRMS spectra of the final products. Acknowledgements Rodrigo Razo (RSRH) thanks to the Laboratorio Nacional de Supercómputo (LNS, Puebla) for the computer time, and Dr. Zeferino Gómez-Sandoval of the University of Colima for the software
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Published 08 Jun 2020

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

  • Dragana Vuk,
  • Irena Škorić,
  • Valentina Milašinović,
  • Krešimir Molčanov and
  • Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

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  • between structure and biological activity. During our previous investigation a series of functionalized compounds with a benzobicyclo[3.2.1]octadiene skeleton was prepared, among which some showed cholinesterase inhibitory properties (Figure 2) [2][3]. The aim of this study was to prepare novel thiophene
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Published 22 May 2020

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

  • Mio Matsumura,
  • Tsutomu Takahashi,
  • Hikari Yamauchi,
  • Shunsuke Sakuma,
  • Yukako Hayashi,
  • Tadashi Hyodo,
  • Tohru Obata,
  • Kentaro Yamaguchi,
  • Yasuyuki Fujiwara and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

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  • The synthesis of organoselenium compounds and their biological activity have attracted considerable attention in research fields directed to drug discovery [1][2][3][4][5][6][7][8][9][10][11][12][13]. Among these compounds, heteroaryl selenides and heteroaryl diselenides have been synthesized by a
  • variety of methods [14][15], and many of the targets exhibited biological activity (Figure 1). For example, bis(2-pyridyl) diselenide I has the potential to mitigate oxidative stress and inhibits the AChE activity [16], bis(quinolin-8-yl) diselenide (II) exhibited antioxidant activity in a skin cell model
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Published 20 May 2020

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

  • Péter Bagi,
  • Réka Herbay,
  • Nikolett Péczka,
  • Zoltán Mucsi,
  • István Timári and
  • György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

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  • importance for biologically active compounds, as specific functional groups are necessary to have a desired biological activity. Considering the functionalization of the five-membered P-heterocycles, the derivatives containing double bond(s) (i.e., phospholenes or phospholes) are of special importance, as a
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Published 22 Apr 2020

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

  • Dong Cai,
  • ZhiHua Zhang,
  • Yufan Meng,
  • KaiLi Zhu,
  • LiYi Chen,
  • ChangXiang Yu,
  • ChangWei Yu,
  • ZiYi Fu,
  • DianShen Yang and
  • YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

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  • [3], antitumor [4], and antibacterial [5] activity and their proberties as hepatic protective agents [6]. Over the past few decades, the emphasis was placed primarily on explaining structure–activity relationships of 18β-glycyrrhetinic acid derivatives to enhance their biological activity. The
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Published 21 Apr 2020
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