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

• highly bioactive compounds that can be converted into drug candidates in a fast and efficient manner containing these moieties is the molecular hybridization [8][9][10]. It consists of covalently joining of two or more pharmacophoric fragments to provide new hybrid compounds with improved efficacy and

• structural diversity and complexity compared to classical 3- or 4-CRs [17][18][19]. In the same context, the hybridization of 1,5-disubstituted tetrazoles with an indole moiety using I-MCRs such as the Ugi-azide reaction as a key step, is very limited. To our knowledge, only three reactions have been

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

• thermostable components of functional organic materials. Keywords: molecular hybridization; nitric oxide; nitrogen heterocycles; 1,2,5-oxadiazoles; 1,2,3-triazin-4-one; Introduction Nitrogen heterocycles are a significant and broad class of organic substances included in the structure of various natural

• agents contain a 1,2,3-triazine ring [37][38][39]. The structures of some bioactive 1,2,3-triazin-4-one derivatives are shown in Figure 1. Hence, one can assume that molecular hybridization of the 1,2,3-triazin-4-one moiety with the 1,2,5-oxadiazole core can lead to a significant modification of the

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• . This method allows for the hybridization of complex bioactive and fluorescent-labeled carboxylic acids with diaryliodonium(III) salts. Keywords: auxiliary ligand; diaryliodonium(III) salts; hybridization; hypervalent iodine; organocarboxylates; Introduction Hypervalent iodine compounds are an

• series of functional groups. As a result, this process can be applied for the unique hybridization of biologically active and fluorescently-labeled carboxylic acids with diaryliodonium(III) salts. We anticipate that this study will encourage the incorporation of diaryliodonium(III) carboxylates in

Spin and charge interactions between nanographene host and ferrocene

• Akira Suzuki,
• Yuya Miyake,
• Ryoga Shibata and
• Kazuyuki Takai

Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89

• FeCp2). The presence of the exchange interaction by hybridization between FeCp2+ orbitals and edge-state orbitals is suggested in addition to the magnetic dipolar interaction. The observed induction and modulation of the spin magnetism by the interfacial interactions between magnetic nanographene host

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• . Additionally, transient PL decay spectra of TPECNz in solvents of different polarities showed a single exponential decay in nanosecond ranges (Figure 3c), signifying that the excited state responsible for the PL emission originates from the hybridization between LE and CT excited states or HLCT state, not a

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

• Carlee A. Montgomery and
• Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

• strength of a σ-hole typically increases with polarizability within the same group (I > Br > Cl >> F) [41][46][47]; however, the electron attracting abilities of the host [31][46], the electronegativity of the halogen atom [41] and, the degree of spn-hybridization in the covalent σR–X bond can also

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• ascorbate in DMSO (Scheme 9). According to UV–vis and circular dichroism (CD) spectrum measurements, the authors state that the formation of the dimer of porphyrin 50 can be attributed to DNA hybridization and through-space electronic interactions. In this investigation, it was found that the DNA serves as

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

• Eric Gayon,
• Guillaume Lefèvre,
• Olivier Guerret,
• Adrien Tintar and
• Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

• efficiently applied at large industrial scales. Extension of such methods to more challenging hybridization patterns in cross-coupling chemistry applied to synthesis of other insect pheromones is currently investigated in our groups. Structure of the (8E,10Z)-tetradecadienal (1, sex pheromone of the horse

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• studies, one of us (M. R. E. A.) felt intrigued by the potential of chemical hybridization of cholesterol through simple connections of pharmacophores including sugars, chalcones, quinolone, theophylline, and ferrocene using click chemistry [9][10][11]. Following this strategy, cholesterol was

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

• Almaz A. Zagidullin,
• Farida F. Akhmatkhanova,
• Mikhail N. Khrizanforov,
• Robert R. Fayzullin,
• Tatiana P. Gerasimova,
• Ilya A. Bezkishko and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

• objects of growing interest in the fields of coordination chemistry [3][4][5] and asymmetric catalysis [6][7]. Due to the sp2-hybridization of the phosphorus atom, phosphaferrocenes are commonly regarded as phosphorus ligands with weaker σ-donor character than classical tertiary phosphines and stronger π

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• 27272, Sharjah, United Arab Emirates The Regional Center for Mycology and Biotechnology, Al-Azhar University, Nasr City, Cairo, 11371, Egypt Department of Chemistry, The University of Jordan, Amman 11942, Jordan 10.3762/bjoc.18.63 Abstract A new chemical library based on the hybridization of cholic

• chemical library based on the hybridization of cholic acid with the heterocyclic moiety 1,3,4-oxadizole was synthesized. All new compounds were unambiguously characterized by various spectroscopic techniques. The newly synthesized compounds were assessed in vitro for their antimicrobial activities

Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines

• Marco Manenti,
• Leonardo Lo Presti,
• Giorgio Molteni and
• Alessandra Silvani

Beilstein J. Org. Chem. 2022, 18, 303–308, doi:10.3762/bjoc.18.34

• oxindoles [7][8][9][10][11] and also of aminoboronic acids [12], we recently exploited a molecular hybridization strategy to synthesize chiral oxindole-based β-aminoboronic acids and spiro derivatives [13]. Apart from our work and a quite recent report describing a useful Cu-catalyzed enantioselective

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• unmodified PS-ASO [43]. It is important to notice that C-5 modifications, besides resulting in improved nuclease stability and providing improved target hybridization, allow for activation of RNase H. This was demonstrated by Matsuda and co-workers when they incorporated modification 2 or 3 into a 17-mer ON

• better hybridization properties than LNA-thymidine; however, only modification 22 gave significant increases in Tm relative to modification 19 used as control. This finding was ascribed to both the extended π-conjugation of the alkynyl-functionalized nucleobase and stabilizing electrostatic interactions

• effects of different amine-functionalized groups. Beginning with the 2’-O-alkylated RNA nucleotides (Table 4) it has been shown that the introduction of an aminopropyl group via 2’-O-alkylation (modification 34) leads to moderately improved hybridization properties for the modified ON against its RNA

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

• involving PNA usually follow the order PNA–PNA > PNA–RNA > PNA–DNA [20][21]. Hybridization of PNA with complementary nucleic acids is enthalpy driven, involving large favorable gains in enthalpy compensated by significant unfavorable entropy, as typically observed for nucleic acid complexes [22]. The

• greatly improved cellular uptake of γ-GPNA. Others have also investigated positively charged α- and γ-modifications of the PNA backbone, and most of them showed promising hybridization properties and improved cellular uptake [82][83][84][85][86]. Very recent work has used α- and γ-positions of the PNA

• functionalities have been introduced in PNA to improve water solubility and better mimic DNA/RNA structure. One of the early studies was on chimeras of PNA and phosphono-PNA (Figure 5) that improved water solubility and in some cases resulted in stronger hybridization with complementary DNA and RNA [90]. The

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• complementary base pairs was monitored by UV melting curve analysis [33]. Hybridization data revealed that the synthesized double-headed nucleotide recognized itself either through formation of Watson–Crick base pairs with two complementary adenosines or through the formation of T:T (thymine:thymine) base pairs

• then incorporated into oligonucleotide sequences, followed by thermal hybridization studies that indicated that the 5′-(S)-C-position is ideal for placing an additional nucleobase in the minor groove and interstrand stacking effects decreased with an increase in the length of the linker [31][65

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• attributes, nuclease stability, and hybridization to single and double stranded nucleic acid targets have led to studies to investigate 3'-NP DNA for antisense and antigene purposes. For example, as an antisense agent in the treatment of human leukemia [67], as an inhibitor of transcription elongation

•  7D) monomer which has been shown to stabilize oligonucleotides similarly to unmodified LNA with a nuclease resistance greater than PS-modified oligonucleotides [157]. Incorporation of selenium at C2' in a thymine-bearing LNA nucleoside (Figure 7E) has been demonstrated to have a hybridization ability

• ]. Hybridization studies of uniformly modified ANA of mixed nucleobase composition to complementary RNA revealed reduced thermal stability relative to the corresponding DNA/RNA duplex by approximately 1.5 °C per modification [182][183]. A significant reduction in stability of the duplex was observed in the binding

Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions

• Jean C. Kazmierczak,
• Roberta Cargnelutti,
• Thiago Barcellos,
• Claudio C. Silveira and
• Ricardo F. Schumacher

Beilstein J. Org. Chem. 2021, 17, 234–244, doi:10.3762/bjoc.17.24

• (3n) in 70% yield (Table 2, entry 14). We also noted that the hybridization of the adjacent carbon atom bonded to the ester group had a direct effect on the formation of the product 3. For instance, comparing entry 1 with entries 15 and 16 in Table 2, we observed a sudden decrease in the reaction

Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups

• Benjamin Jeffries,
• Zhong Wang,
• Robert I. Troup,
• Anaïs Goupille,
• Jean-Yves Le Questel,
• Charlene Fallan,
• James S. Scott,
• Elisabetta Chiarparin,
• Jérôme Graton and
• Bruno Linclau

Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182

• to the hybridization state of cyclopropyl carbon atoms. However, β-fluorination of the oxetanyl derivative F1 led to a lipophilicity increase. With the caveat that the value for F1 is not a measured value and the difference is well within the standard deviation (0.23 logP units), this increase is in

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

• classes depending on the nitrogen atom hybridization and the substitution of the N atom, including iminyl, amidyl, aminyl, and aminium units (Scheme 26). The reactivity depends on the philicity of each species. In a general manner, NCRs are prone to the addition to unsaturated systems, either inter- or

A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

• Ekaterina A. Bryushkova,
• Erik R. Gandalipov and
• Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

• aptamer module. This solves a problem of secondary structure in hybridization with the target sequence of full-length mRNA. It was shown that within 24 hours the proposed sensor specifically recognized both a synthetic 60-nucleotide RNA fragment (LOD is 1.4 nM of RNA fragment at 37 °C) and a full-sized

• , deoxyribozyme-based biosensors [5], and aptamer-based biosensors [3]. The detection mainly relies on a specific hybridization between a well-known target fragment and the biosensor strands. To increase selectivity NAs are also created as binary or split construction. Due to the simplicity, the DNA hybridization

• assembling was evaluated using agarose gel electrophoresis (Figure 1E). The single band proved that in the chosen conditions there was a complete hybridization of all 5 strands into an integrated SDFS complex. After hybridization between SDFS and 60-AR_RNA we expected to see a specific cleavage of target

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• )=C bond disappeared and two new signals appeared at around 68–69 ppm (quaternary C) and 51–60 ppm (CH). These facts are consistent with the expected hybridization change from Csp2 to Csp3 after formation of the cyclobutane ring. Determination of the crystal structure of complex 4a, which is shown in

Towards triptycene functionalization and triptycene-linked porphyrin arrays

• Gemma M. Locke,
• Keith J. Flanagan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

• , owing to electron transfer from the zinc porphyrin unit to the nickel porphyrin unit. Initial studies have shown the promise of triptycene as a linker for electron transfer studies, and an expanded library could lead to further interesting results where the linearity, hybridization and accessibility of

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• nodal plane near the 1,7-positions in the HOMO and smaller MO coefficients at the 2,6-positions than those at the 3,5-positions. Rather, a stabilization of the LUMO energies is found in 5a and 6a even though the MO hybridization of the BODIPY core with π-orbitals of ethynyl moieties is less affected

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• . The π-acceptor character of phosphorus can be reinforced by the presence of oxygen and/or nitrogen whilst σ-donating potency of nitrogen can be manipulated by switching between sp3 and sp2 hybridization [9][49][50]. The synthesis of phosphines is quite delicate because when exposed to air, some of

Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides

• Sabrina Müller,
• Jannik Paulus,
• Jochen Mattay,
• Heiko Ihmels,
• Veronica I. Dodero and
• Norbert Sewald

Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8

• major groove recognition [21][22]. Woolley et al. reported other photoisomerizable Tf mimetics that interacted through the major groove [23][24]. Hybridization of DNA [25][26][27] or PNA/DNA [28] can be light-controlled by azobenzene-modified DNA. While DNA covalently modified with azobenzene moieties