[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• in the use of these compounds. This is quite understandable: compounds with unique optical [2][3][4], electrophysical [5][6][7], mechanical [8][9][10], tribological [11][12][13], sorption [14][15][16][17], and biological properties [18][19][20], and even new dyes and catalysts [21][22][23][24][25

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• ][9][10][15]. Biochemical characterization of 9,11-secosterols has so far mainly relied on the identification and purification of natural products from marine invertebrates. The intriguing profile of biological properties has prompted synthetic studies of this class of secosterols. The majority of

• mild reaction conditions, and the protocol tolerates several functional groups. It is an environmentally benign approach, totally excluding the use of highly toxic oxidants. Our synthetic scheme provides a direct entry to structurally diverse 9,11-secosterols, enabling also studies of their biological

• properties. Further research to broaden the scope of the presented synthetic scheme is ongoing. Experimental General data Full assignment of 1H and 13C chemical shifts were based on the 1D and 2D FT NMR spectra, measured with a Bruker Avance III 400 MHz or a Bruker Avance III 800 MHz instrument. Residual

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

• Xiaojuan Li,
• Qiang Zhang,
• Weigang Zhang,
• Jinzhu Ma,
• Yi Wang and
• Yi Pan

Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49

• . Keywords: alkenes; difunctionalization; metal-free; photoredox; trifluoromethylthiolation; Introduction The incorporation of fluorine atoms into drug molecules will significantly enhance the physical, chemical, and biological properties of the pharmaceuticals [1][2][3][4][5][6]. Modifying drug candidates

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

• Yamato Fujihira,
• Yumeng Liang,
• Makoto Ono,
• Kazuki Hirano,
• Takumi Kagawa and
• Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

• their biological properties, bioavailability, and ADME [7][8]. While tremendous methodologies have been developed for the synthesis of organofluorine compounds [9][10], many of the laboratory methods are not always suitable for industrial production in terms of their synthetic complexity, handling, and

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

Au(III) complexes with tetradentate-cyclam-based ligands

• Ann Christin Reiersølmoen,
• Thomas N. Solvi and
• Anne Fiksdahl

Beilstein J. Org. Chem. 2021, 17, 186–192, doi:10.3762/bjoc.17.18

• ][20][21]. Simple [Au(III)–cyclam] complexes have been investigated for various biological properties [22][23][24][25][26][27][28][29]. Particularly, studies have focused on their potential in vitro anticancer properties [24][26][29], the activity against a falciparum strain [22], the in vitro DNA

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• Omura’s group in 1995 [3]. Inthomycin A ((+)-1) displays moderate antifungal activity against cellulose-containing Phytophthora parasitica and Phytophthora capsici [4]. Inthomycins were reported to possess many interesting biological properties, which include the specific inhibition of the cellular

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

• nature, but not less important. They possess biological properties, such as nicotinic acetylcholine receptor (nAChR) ligand [10][11], CNS (central nervous system) activity [12][13], and chemical defense [14][15][16]. Structurally, homotropane alkaloids have different skeletons including [3.3.1], [4.2.1

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

• , optical, and biological properties upon a careful selection of the substitution pattern [9], continually encouraged the scientific community to search for new powerful representatives and to elaborate advantageous synthetic protocols. Under chemical, biochemical, or electrochemical conditions the

• biological properties exhibiting enzymatic activity as potent and selective protease inhibitors, fungicidal and herbicidal activity [17], we designed an efficient, simple, and ecofriendly synthetic procedure for the preparation of new synthetic compounds containing joint phenothiazine/ferrocene and α-amino

Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction

• Daniela Rodrigues Silva,
• Joyce K. Daré and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2020, 16, 2469–2476, doi:10.3762/bjoc.16.200

• soil sorption and bioconcentration of organic compounds. Since the C–F bond is the most polar in organic chemistry, the orientation of fluorine substituents originating from the rotation around C–C(F) bonds should affect the polarity and, consequently, the physicochemical and biological properties of

• substituents originated from the rotation of fluorine-containing C–C bonds should affect the polarity and, therefore, the physicochemical and biological properties of organofluorine compounds. However, there is a lack of studies that explain how these well-known conformational effects directly alter

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

• Mysore Bhyrappa Harisha,
• Pandi Dhanalakshmi,
• Rajendran Suresh,
• Raju Ranjith Kumar and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

• ][22][23][24][25][26]. Some oxazoles play a significant role in biological properties such as TRPV1 antagonistical activity, antifungal, analgesic, anti-inflammatory, antiproliferative, antileukemia, anticancer [27][28][29][30][31][32] and enzyme inhibitory activities [33][34][35][36][37][38][39][40

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

• , there have been only 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, starting from BER and some α-bromohydrazones. On the other hand, also the

• [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

• insertion in the original molecule of different functions with their own peculiar features. Often, the biological properties of the resultant derivatives are not simply attributable to the sum of the characteristics shown by the individual moieties, but synergistic effects can increase their effectiveness

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• protein–protein and protein–ligand interactions and consequently metabolic processes [20][21]. Fluorinated phenylalanines (FPhe) have been incorporated into various proteins and enzymes [22][23][24][25] with advantageous biophysical, chemical, and biological properties, and their effect on the stability

• development of efficient synthetic protocols to FAAs. Among them, a range of fluorinated phenylalanines emerged, that have enhanced the biophysical, chemical and biological properties of bioactives. Accordingly, synthetic approaches to five distinct classes of fluorinated analogues were reviewed here

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

• Phil M. Pithan,
• Sören Steup and
• Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

• -binding properties to be used as DNA-sensitive fluorescent probes in cell imaging [60][61][62] or as photoswitchable DNA ligands [63]. Therefore, we were interested in a combination of the photochromic properties of the spirooxazine moiety with the advantageous photophysical and biological properties of

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K₂CO₃/n-Bu₄PBr in water

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati and
• Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

• into organic molecules can dramatically influence their physiochemical and biological properties in comparison with non-fluorinated analogs [18] (see compounds I and II in Figure 1). Many pharmaceuticals and agrochemicals developed in recent decades have either a fluorine atom or a trifluoromethyl

• preparation of 3,3'-, and 3,6'-DIMs, which are known to possess a wide variety of biological activities, including anti-inflammatory, and anticancer effects. Additionally, trifluoromethyl(indolyl)phenylmethanols itselft have various biological properties including anti-HIV activity. The developed new

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• ], antiparkinsonian [6], and anticancer [10] properties. Particularly, triazoles illustrate distinguished moieties well distributed in natural products with biological properties [2][3][4][9][10], including antimicrobial [2], antibacterial [3], antifungal [3], anti-HIV [4], and anticancer [10] activities. One of the

Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction

• Damian Kusy,
• Agata Wojciechowska,
• Joanna Małolepsza and
• Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 15–21, doi:10.3762/bjoc.16.3

• of compounds from a common precursor and enables efficient generation of new chemical entities. Imidazo[1,2-a]pyridine constitutes an appealing scaffold in medicinal chemistry. It is present in a number of compounds, which exhibit many interesting biological properties. Its privileged character is

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

• Renata Kaczmarek,
• Dariusz Korczyński,
• James R. Green and
• Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

• common framework for materials with potent biological properties [6][7][8][9][10]. Modification on this site of the nucleobase usually does not interfere with Watson–Crick base pairing. For example, C-5-modified pyrimidines are well tolerated by commercial polymerases [11][12]. Alkynyl modifications not

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

• represent an important class of nitrogen-containing biologically active compounds which exhibit various biological properties, such as antiviral, antibacterial and anticancer, etc. [55][56][57][58]. Recently, the use of 1,2,3-triazole derivatives as drug candidates has been increased for clinical therapy of

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• chlorins for the development of PDT therapeutics and dependence of their biological properties on the structure of peripheral substituents, we developed a simple synthetic approach for new maleimide derivatives of the fluorinated porphyrins and chlorins. We also believe the synthetic potential of maleimide

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• biological properties. They have been reported to have anticancer [1], antimicrobial [2][3] and antioxidant [3] activities and to act as inhibitors of hepatitis B virus [4]. The dihydro derivatives of tetrazolo[1,5-a]pyrimidines belong to a bit special kind of dihydropyrimidines due to the strong electron

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• modifications, on the terminal functions [28][29], at the core [30] or linked to the core [31], and in the branches [32] have been achieved. In this review, we will gather the syntheses, fluorescence properties, and some biological properties of phosphorhydrazone dendrimers bearing in some part of their

• two different locations in the structure of the dendrimers, and will report at the end the biological properties. Review The synthesis of phosphorhydrazone dendrimers necessitates two steps to build one generation. Starting from a core having P–Cl functions, such as the hexachlorocyclotriphosphazene

• confinement in the double layer dendrimer has a detrimental influence on the TPA properties [63]. Biological properties of dendrimers having TPA properties Most of the water-soluble fluorescent dendrimers shown in the previous paragraphs have been synthesized for diverse biological purposes. The first type of

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives

• Hai-Yun Huang,
• Haoran Li,
• Thierry Roisnel,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2019, 15, 2069–2075, doi:10.3762/bjoc.15.204

• methodology provides a straightforward access to several lilolidine derivatives from commercially available compounds via one, two or three C–H bond functionalization steps allowing to tune their biological properties. Keywords: catalysis: C–C bond formation; C–H bond activation; lilolidine; palladium

• 10 mol % of CuI as catalyst in DMF at 100 °C. The late stage C–H bond functionalization of molecules represents a powerful method for the easy screening of the biological properties of compounds containing a bioactive unit. Since the seminal work by Ohta et al. on the Pd-catalyzed C–H bond

• nicely. Therefore, this methodology provides a straightforward access to a wide variety of α- and β-(hetero)aryl-substituted lilolidines allowing to tune or modify their biological properties. Structures of lilolidine, tivantinib and tarazepide. Access to α- and β-arylated lilolidine derivatives

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• , respectively. The latter compound as an unprotected acid was identified as a component of immunosuppressive thalassospiramide A [95] and siderophores called crochelins [96]. On the other hand, the former one was used in the synthesis of edenine A and D analogues [97] to study their biological properties. When

• as components of a variety of plants and exhibit a wide range of biological properties including inhibition of glucosidases [102]. When the aziridine epoxide 162 was treated with acetic acid the aziridine ring cleavage was observed to give the epoxyaldehyde 178 (Scheme 45) [94]. Catalytic

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• exploitation of the MCR potential in the rapid diversification of steroidal products for screening of their pharmaceutical and biological properties. We expect this review serves as inspiration for the MCR community to further explore the scope of steroids in the development of new reactions and methods