Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

• Anastasia S. Kostyuchenko,
• Tatyana Yu. Zheleznova,
• Anton J. Stasyuk,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2017, 13, 313–322, doi:10.3762/bjoc.13.34

• demonstrated that calculations performed by the hybrid B3LYP functional with a triple-ξ quality basis set almost perfectly describe singlet–singlet π–π* transitions for 2,2':5',2'':5'',2''':5''',2''''-quinquethiophene and 2,5-diphenylfuran. They have further demonstrated that the basis set of double-ξ quality

• shows a small decrease of the displacement of the obtained spectrum compared to triple-ξ quality, while the larger basis sets yield almost identical results. The hybrid B3LYP functional coupled with an integral equation formalism of the polarizable continuum model (IEFPCM) provides a reasonable and

• (Figure 4). Considering the fact that the non-coulombic part of hybrid functionals typically dies off too quickly resulting in lack of precision at large distances and lack of suitability for some tasks associated with electron-excitation modeling, we repeated our calculations with the range-separated

Spectral and DFT studies of anion bound organic receptors: Time dependent studies and logic gate applications

• Srikala Pangannaya,
• Neethu Padinchare Purayil,
• Shweta Dabhi,
• Venu Mankad,
• Prafulla K. Jha,
• Satyam Shinde and
• Darshak R. Trivedi

Beilstein J. Org. Chem. 2017, 13, 222–238, doi:10.3762/bjoc.13.25

• understand the binding mechanism, we have performed a density functional theory (DFT) simulation on the receptor molecules using the GAUSSIAN 09 software package [44]. A closed-shell Becke–Lee–Yang–Parr hybrid exchange–correlation three-parameter functional (B3LYP) [45] along with the 6-311++G(d,p) basis set

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

• Naganna Narra,
• Shiva Shanker Kaki,
• Rachapudi Badari Narayana Prasad,
• Sunil Misra,
• Koude Dhevendar,
• Venkateshwarlu Kontham and
• Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

• phenolics and the lipid involved in one chemical entity [4][5]. Lipids, especially fatty acids and their derivatives are known for their broad spectrum of activity which expands their application in developing new hybrid biomolecules which help in host defenses against potential pathogenic microbes

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• Network “Solar Technologies Go Hybrid”) is gratefully acknowledged.

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

• peptidomimetics with potential biological activity. Keywords: acylhydrazino-peptomers; consecutive Ugi reactions; peptide-peptoid hybrid; peptomer; Introduction In the last decades, increasing efforts have been extensively carried out to improve the pharmacological properties of natural peptides by structural

• structures have also been carried out to obtain the less common but also biologically active azapeptoids [40], hydrazino-azapeptoids [41][42], retro hydrazino-azapeptoids [43] and peptoid-azapeptoid hybrids [39]. Recently, Seo et al. [44] reported the synthesis of a library of peptide-peptoid hybrid (termed

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• biosynthesis (MBP-PCP-Xsta, Table 1, entries 1–4), a PCP-X construct from teicoplanin biosynthesis (MBP-PCP-Xtei, Table 1, entries 5–8) and hybrid PCP-X constructs from A47934 and teicoplanin biosynthesis (MBP-PCPsta-Xtei, Table 1, entries 9–12; MBP-PCPtei-Xsta, Table 1, entries 13–16;) [12]. The influence of

• ion monitoring (SIM) mode. (a) StaF activity against different peptide substrates and using NRPS constructs; the activity of StaF with Tei7-L-Hpg7 (magenta), Tei7-D-Hpg7 (green), Pek7-rac-Hpg7 (orange) and Act7-rac-Hpg7 (blue) were determined; all peptides were bound to wildtype and hybrid PCP-X

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• epoxides are compatible under IFCEA cyclization (as demonstarted previously by us [22][23] and others [29][33]), this methodology should also be applicable with the enantioenriched substrates. Further work is in progress aimed at synthesizing such type of fused hybrid molecules with different ring sizes

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

• ]. AutoDock3 uses an empirical scoring function that has five terms. These terms are weighted with experimental target–ligand data. It can model side chain flexibility of the target molecule. AutoDock Vina is the new generation of AutoDock. The scoring function used in AutoDock Vina is a hybrid scoring

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

• other metals and represent a versatile tool for obtaining hybrid heterocycles with properties that are useful for the development of new advanced materials and for medicinal purposes [1][2][3][4]. Recently, we obtained, by 1,3-dipolar cycloaddition reactions of sydnone-ylides as bis(1,3-dipoles) with

• activated acetylenes, the hybrid structures 1 containing a pyrroloazine (pyrroloisoquinoline or pyrrolophthalazine) connected to the sydnone ring through a keto group [5]. As a result, it was of interest to prepare analogous compounds containing a pyrroloazine directly attached to the C-4 position of a

• proposed structures for the hybrid heterocycles 12. The signals for the endocyclic and exocyclic CO groups of the sydnone moiety are strongly deshielded and the chemical shifts are very close, appearing in the range of 165.5–166.1 ppm, whereas the carbonyls of the ester groups are shielded by 2–3 ppm. Both

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• -transfer characteristics [59][60][61][62][63], as hole-transport materials [64], for applications in mesoporous organo silica hybrid materials [65], and as chromophores in dye-sensitized solar cells [66][67][68]. Furthermore, (oligo)phenothiazines in their native reduced forms display a pronounced ability

• oligophenothiazines [45]. With these geometry-optimized structures in hand the electronic absorptions were calculated with the semiempirical ZINDO-CI, and TD-DFT (B3LYP and CAM-B3LYP, an implemented hybrid exchange-correlation functional [81], using the polarizable continuum model (PCM) [82] applying dichloromethane

Experimental and theoretical investigations on the high-electron donor character of pyrido-annelated N-heterocyclic carbenes

• Michael Nonnenmacher,
• Dominik M. Buck and
• Doris Kunz

Beilstein J. Org. Chem. 2016, 12, 1884–1896, doi:10.3762/bjoc.12.178

• MHz, CDCl3) δ −55.8 (s, Se); HRMS (ESI+) m/z: 360.11023 [M+] (calcd 360.10992). Left: resonance hybrid of the dipyrido carbenes dipiy and dipiytBu. Right: two canonical forms of the dipyridocarbene according to Weiss and co-workers. 13C NMR spectra (carbonyl region, 125 MHz) of the reaction of 1a with

Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

• Sambasivarao Kotha and
• Rama Gunta

Beilstein J. Org. Chem. 2016, 12, 1877–1883, doi:10.3762/bjoc.12.177

• evident that the allyl groups present in 2a should be in endo configuration. To confirm the configuration of the allyl groups, the X-ray structure of previously reported oxa-bowl/propellane hybrid (15) [38] was also recorded and it is in agreement with the above findings (Figure 3). These results

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• characteristics of the metal-containing assemblies depend on the electronic influence of the substituents attached to the terpyridine unit as well as to the metal ion [7]. While the number of publications concerning applications or investigations of inorganic–organic hybrid structures has increased enormously

• oscillator strengths for the herein described compounds 4a and 4b were calculated with time-dependent density functional theory (TDDFT) utilizing the following functionals: B3LYP [34][35][36][37], Coulomb-attenuated B3LYP (CAMB3LYP) [38], hybrid TPSS (TPSSH) [39], and M06 with double Hartree–Fock exchange

• (M062X) [40]. Of these four functionals, B3LYP and CAMB3LYP are hybrid functionals with 20% Hartree–Fock exchange content, the later one incorporated with enhanced Hartree–Fock (HF) exchange in the long-distance ranges in order to correctly describe the charge transfer (CT) states. TPSSH is a hybrid

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• Spectrometry Service Facility of the Organic-Chemical Department of the University of Heidelberg using the following instruments: Vacuum Generators ZAB-2F, Finnigan MAT TSQ 700, JEOL JMS-700, Bruker ICR Apex-Qe hybrid 9.4 T FT-ICR. In general the ionization method was specified. Apart from the method of

Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands

• Dirk Meyer and
• Thomas Strassner

Beilstein J. Org. Chem. 2016, 12, 1557–1565, doi:10.3762/bjoc.12.150

• -NHC ligand [33]. To study the differences between both systems we synthesized palladium [34] and platinum [35] “hybrid complexes” with ligands combining both structural elements the pyrimidine as well as the NHC fragment. We also used density functional theory (DFT) calculations to investigate the

• should be active according to the proposed catalytic cycle, which starts with an electrophilic substitution reaction. We therefore set out to synthesize the corresponding methyl complexes for the “hybrid ligand” with chloro- and trifluoroacetato ligands. Results and Discussion Synthesis Some time ago we

• -CH ph), 135.8 (ipso-C ph), 145.6 (o-C ph), 155.3 (ipso-C pym), 156.1 (m-CH pym), 157.0 (m-CH pym), 194.7 (carbene-C). ESIMS: 444.1 [M + H]+. Computational details All calculations were performed with the Gaussian 09 software [55]. The geometries were optimized using the density functional hybrid

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• [4]. Oxygen heterocycles are mainly found in carbohydrates, polyketides, peptides and terpenoids. Nitrogen heterocycles are part of peptides and alkaloids. Both can of course also occur in the respective hybrid natural products. Sulphur-containing heterocycles are present in few polyketides and more

• enzymatic units that introduce nitrogen, we expanded the scope of this article to those products of polyketide synthase–non ribosomal peptide synthetase (NRPS) hybrid systems in which the polyketide portion strongly dominates the overall structure and in which the amino acid nitrogens are incorporated into

• characterised in the pederin (24) and the ambruticin (28) biosynthetic pathways (Scheme 3 and Scheme 4) [14][15]. PedPS7 is a monofunctional pyran synthase (PS) domain that was predicted to catalyse ring formation from an α,β-unsaturated intermediate in the biosynthesis of the PKS–NRPS hybrid product pederin

The hydrolysis of geminal ethers: a kinetic appraisal of orthoesters and ketals

• Sonia L. Repetto,
• James F. Costello,
• Craig P. Butts,
• Joseph K. W. Lam and
• Norman M. Ratcliffe

Beilstein J. Org. Chem. 2016, 12, 1467–1475, doi:10.3762/bjoc.12.143

• and the MMFF force field. Final molecular geometries were optimised using the Gaussian09 [49] with density functional level of theory, using the hybrid functional B3LYP/6-31G* to optimise structures [50][51][52], with convergence criteria for maximum and RMS force (0.000450 and 0.000300 in atomic

Ring-whizzing in polyene-PtL₂ complexes revisited

• Oluwakemi A. Oloba-Whenu,
• Thomas A. Albright and
• Chirine Soubra-Ghaoui

Beilstein J. Org. Chem. 2016, 12, 1410–1420, doi:10.3762/bjoc.12.135

• 77006, USA 10.3762/bjoc.12.135 Abstract Ring-whizzing was investigated by hybrid DFT methods in a number of polyene–Pt(diphosphinylethane) complexes. The polyenes included cyclopropenium+, cyclobutadiene, cyclopentadienyl+, hexafluorobenzene, cycloheptatrienyl+, cyclooctatetraene

• using the B3LYP hybrid functional and a different basis set. The computed geometric parameters for the molecules are very close to each other. One Pt–C bond is short (2.10 Å) while the other two flanking bonds are 2.52 Å. Thus, 20 strongly resembles an η1 14 electron complex with a “T” shaped geometry

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• College, 771 Nakakuki, Oyama, Tochigi 323-0806, Japan 10.3762/bjoc.12.134 Abstract The ever increasing demand for clean energy has encouraged researchers to intensively investigate environmentally friendly photovoltaic devices. Inorganic–organic hybrid perovskite solar cells (PSCs) are very promising due

• ; hole transport; perovskite solar cell; polycondensation; Introduction Inorganic–organic hybrid perovskite solar cells (PSCs) have recently received significant attention due to their remarkably high power convention efficiencies (PCEs). After the seminal study reported by Miyasaka et al. in 2009 with

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

• ligands. The use of phosphonate ligands to modify the nanoparticle surface drew a lot of attention in the last years for the design of highly functional hybrid materials. Here, we report a methodology to synthesize bisphosphonates having functionalized PEG side chains with different lengths. The key step

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• , with a predominance of hybrid PKS-NRPS systems [37]. M. xanthus strain DK1622 is responsible for the synthesis of metabolites like DKxanthene-534 (8, Figure 4), a pigment required for fruiting body formation and sporulation processes [37] and the siderophore myxochelin A (9), which belongs to a class

• our group revealed that this organism displays, analogous to the previously discussed example M. xanthus strain DK1622, a plethora of cryptic gene clusters, e.g., five NRPS, four hybrid PKS-NRPS, one PKS-NRPS-lantipeptide, three lantipeptide and numerous bacteriocin- and terpene-encoding gene loci. A

• corresponding hybrid PKS-NRPS machinery responsible for metabolite biosynthesis [57]. The molecule was shown to have cytotoxic effects towards HeLa-S3 cells (IC50 = 12 μM). The genus Enhygromyxa All Enhygromyxa species isolated to date are halophilic and considered as truly marine myxobacteria. The initial

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• precatalysts in the transfer semihydrogenation of alkynes to Z-alkenes. Messerle et al. [26] synthesized a series of new cationic Rh(I), Rh(III) and Ir(III) complexes containing hybrid bidentate N-heterocyclic carbene-1,2,3-triazolyl donors. We [27] have synthesized a series of nonsymmetrical pincer palladium

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

• Pseudomonas strains. Analogue 97 is an interconverted version of 96 and displayed a comparatively poor activity. The most active analogue was compound 98 which is a hybrid type of the aforementioned analogues 95–97. The results indicate that a lipophilic side chain and guanidine groups are necessary for

• antibacterial potency. Compounds 95–98 showed antibacterial activity, with the branched-type compound 96 (MIC values between 8 μg/mL and 16 μg/mL) and the hybrid-type compound 98 (MIC between 4 μg/mL and 8 μg/mL) being the most active congeners. A limitation of both analogues 96 and 98 is their increased

• give uridine-5'-aldehyde 99. Aldehyde 99 then supposedly undergoes an aldol addition with glycine 100 as the enol(ate) component, thus furnishing the amino acid–nucleoside hybrid 5'-C-glycyluridine (GlyU, 101). Alkylation of the 6'-amino group is then achieved by reaction with S-adenosyl methionine

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• one of the chiral grooves of the triple-helix. In contrast, the second project on cavitands was focused on making a wholly synthetic hydrophobic pocket rather than one in a proteinaceous hybrid. We needed a peptide synthesizer for the canyons project and a round bottom flask for the cavitand work, and

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

• , our group has developed a hybrid drug combining silibinin with tacrine (a potent acetylcholinesterase inhibitor for treatment of Alzheimer’s disease), which shows neuro- and hepatoprotective effects exceeding the cytoprotective effects of silibinin and effectively counteracts tacrine’s dose-dependent

• been used by us since we wanted to obtain hybrid esters for medicinal chemical purposes [27]. As expected, in all cases, two products were detected in different ratios according to the different ratios of Ph3P and DIAD used (Table 1, entries 1–4). Spectral data of the two products confirmed their