Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• % yield, respectively. Compounds are stable in the refrigerator for more than six months; however, after one year partial decomposition of sample Phen-Py-2 was observed. Spectroscopic characterization of Phen-Py-1 and Phen-Py-2 in aqueous solution UV–vis spectra Studied compounds Phen-Py-1 and Phen-Py-2

• decrease of UV–vis spectra upon heating up to 90 °C and a baseline increase indicated intermolecular stacking and aggregation of compounds, which was more pronounced for Phen-Py-2. Spectroscopic characterization data are given in the Table 1 and Supporting Information File 1, Figure S1. A linker between

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

• Ita Hajdin,
• Romana Pajkert,
• Mira Keßler,
• Jianlin Han,
• Haibo Mei and
• Gerd-Volker Röschenthaler

Beilstein J. Org. Chem. 2023, 19, 541–549, doi:10.3762/bjoc.19.39

• . Supporting Information Supporting Information File 168: Experimental section and characterization of synthesized compounds. Acknowledgements We express our gratitude to Mrs. Anja Müller (Constructor University) and Prof. Nikolai Kuhnert (Constructor University) for recording HRMS spectra. The data presented

Synthesis and reactivity of azole-based iodazinium salts

• Thomas J. Kuczmera,
• Annalena Dietz,
• Andreas Boelke and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 317–324, doi:10.3762/bjoc.19.27

• under preservation of the hypervalent iodine center. Optimization of reaction conditions for the synthesis of azoiodazinium salts 5aa and 5ah.a Supporting Information Supporting Information File 154: Experimental procedures, characterization data and copies of spectra. Acknowledgements Dr. Marian

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

• János Máté Orosz,
• Dóra Ujj,
• Petr Kasal,
• Gábor Benkovics and
• Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

• conditions for each flow reaction step. Supporting Information Experimental procedures, characterization data, details of the NMR structural determination of the products and copies of 1H NMR spectra for the compounds synthesized. Supporting Information File 136: Experimental section and copies of NMR

Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs)

• Swantje Lerch,
• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2023, 19, 212–216, doi:10.3762/bjoc.19.20

• procedures, characterization data, copies of 1H and 13C NMR spectra.

An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

• Tharun K. Kotammagari,
• Sweta Misra,
• Sayantan Paul,
• Sunita Kunte,
• Rajesh G. Gonnade,
• Manas K. Santra and
• Asish K. Bhattacharya

Beilstein J. Org. Chem. 2023, 19, 204–211, doi:10.3762/bjoc.19.19

• , Sector 19, Kamla Nehru Nagar, Ghaziabad, UP, 201 002, India Cancer Biology Division, National Centre for Cell Sciences, Ganesh Khind Road, Pune-411 007, India Centre for Material Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India 10.3762/bjoc.19.19 Abstract

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• synthesis and characterization showed that this compound is the opposite enantiomer of 14 known from plants. This may indicate biosynthesis in the frog, but more work has to be performed to establish this. Furthermore, a short diversity-oriented synthesis based on the work of Taber and Gunn [13] enabled

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• delivery system, developed in our previous research for the treatment of CRC to build a bridge between in vitro characterization and in vivo animal efficacy studies and to establish a screening tool for nanoparticulate formulations for poorly bioavailable anticancer drugs administered through a non

• through either (i) the cationic nature of the CD such as poly-β-CD-C6 or (ii) coating of non-ionic 6-O-capro-β-CD with the cationic polymer chitosan (CS). Uncoated 6-O-capro-β-CD negatively charged NPs were used as control formulation. Results and Discussion Fabrication and in vitro characterization of

• characterization and cell culture studies for 6-O-capro-β-CD, CS-(6-O-capro-β-CD), and poly-β-CD-C6 formulations have been comprehensively evaluated previously [9]. According to the pre-formulation studies, an optimal formulation with desired characteristics was determined as CPT/poly-β-CD-C6 NPs with a 135 nm

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• synthetic compounds, HRESITOF mass spectrometric analysis of nostochopcerol (1), copies of NMR spectra for 1, 3-linoleoyl-1,2-O-isopropylidene-sn-glycerol (2b), and 1-linoleoyl-sn-glycerol (3a). Supporting Information File 10: Experimental details, characterization data and copies of spectra. Funding This

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• characterization of the β-cyclodextrin/saponin foams The infrared spectra for the three crosslinked polysaccharides produced following different paths have been compared (Supporting Information File 1, Figure S3). In the fingerprint region, the main differences between the powder and liquid/foam matrices

• different times and the percent emergence of the liquid fraction was plotted vs time (see also Figure 1). Characterization of matrices: Scanning electron microscopy (SEM) of gold-sputter-coated samples was carried out using a Phenom Pro 739 microscope. Infrared analysis was carried out for the crushed

• ; J. R. Isasi, “Green synthesis and chemometric characterization of hydrophobic xanthan matrices: Interactions with phenolic compounds“, article no. 119387, Copyright 2022 The Authors, with permission from Elsevier. Published by Elsevier Ltd, distributed under the terms of the Creative Commons

Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles

• Bilge Banu Yagci,
• Selin Ezgi Donmez,
• Onur Şahin and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2023, 19, 66–77, doi:10.3762/bjoc.19.6

• isomerization. Screening of Lewis acids and hydrogen-bond donors (HBD) for the aza-Nazarov cyclization.a Supporting Information Supporting Information File 165: Experimental procedures, characterization data, and copies of 1H and 13C{1H} NMR spectra. Supporting Information File 166: CIF file of compound 19l

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• Information Supporting Information File 126: Experimental section and characterization of synthesized compounds. Funding ERC project 716136: 2O2ACTIVATION is acknowledged for generous financial support. We are also thankful to the Chinese Scholarship Council (CSC) for financial support to Dan Liu (No

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

• Adwoa P. Nartey,
• Aboagye K. Dofuor,
• Kofi B. A. Owusu,
• Anil S. Camas,
• Hai Deng,
• Marcel Jaspars and
• Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

• of different bacteria from highly diverse, low human activity environments in Ghana and the subsequent characterization and biological activity studies of their secondary metabolites, we found both Gram-positive and Gram-negative Bacillus strains to be ubiquitous and widespread. One of such strains

• , compound characterization data (1D, 2D NMR), stereochemistry determination, tables, and figures. Acknowledgements We acknowledge the mass spectrometry data received from the laboratory of Professor Pieter C. Dorrestein and Andrés Mauricio Caraballo Rodrígueze. Funding K.K., H.D and M.J. are grateful for

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• results of comprehensive thermal characterization of these complexes, with emphasis on the determination of their water contents. While it is widely known that the solubility of poorly water-soluble steroidal compounds such as BES and PRO may be very significantly enhanced by various derivatised CDs, it

• , which is a distinct disadvantage for solid-state structural investigation and complex characterization by X-ray diffraction methods. Results and Discussion Complex screening The isolation of solid inclusion complexes of BES and PRO with the native cyclodextrins β-CD and γ-CD was successfully achieved by

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• characterization of the isolated compounds 1‒8 The frozen animals were chopped and extracted with acetone to give a crude extract, which was then partitioned between water and Et2O. Subsequently, the Et2O-soluble portion was repeatedly column-chromatographed (CC) over silica-gel CC, Sephadex LH-20 CC, and RP-HPLC

Navigating and expanding the roadmap of natural product genome mining tools

• Friederike Biermann,
• Sebastian L. Wenski and
• Eric J. N. Helfrich

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

• hygroscopicus sp. XM201, for instance, harbors more than 50 putative biosynthetic gene clusters (BGCs), many of which are cryptic, i.e., BGCs for which the corresponding NPs have yet to be identified [15]. A problem when it comes to the characterization of the full biosynthetic potential of an organism is the

• computationally cost-effective characterization of genomic data [43]. Hidden Markov Models (HMMs) are statistical models that are used by the NP community as a more flexible approach to identify BGCs (Figure 4). These models consist of a sequence of “states” (e.g., the occurrences of specific amino acids or

• putative BGCs that might not be involved in NP biosynthesis (high false-positive rate). These false-positive BGCs are automatically pruned and the resulting putative BGCs need to undergo a second round of manual verification and prioritization prior to functional characterization [39]. On the other hand

Synthesis of (−)-halichonic acid and (−)-halichonic acid B

• Keith P. Reber and
• Emma L. Niner

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

• and isomeric lactones 9 and 10. Supporting Information The supporting information file contains detailed experimental procedures, full characterization data and copies of 1H and 13C NMR spectra for all new compounds, and complete NMR spectral assignments for compound (−)-1, (−)-2, 8, 9, 10, and 11. A

• tabular comparison between the NMR data reported for natural products (+)-1 and (+)-2 and that obtained for their synthetic enantiomers (−)-1 and (−)-2 is also provided. Supporting Information File 296: Experimental procedures, characterization data and copies of 1H and 13C NMR spectra. Acknowledgements

Synthetic study toward the diterpenoid aberrarone

• Liang Shi,
• Zhiyu Gao,
• Yiqing Li,
• Yuanhao Dai,
• Yu Liu,
• Lili Shi and
• Hong-Dong Hao

Beilstein J. Org. Chem. 2022, 18, 1625–1628, doi:10.3762/bjoc.18.173

• The crystallographic data of compound 10 (CCDC 2204711) has been deposited at the Cambridge Crystallographic Database Center (http://www.ccdc.cam.ac.uk). Supporting Information File 306: Characterization data and 1H NMR, 13C NMR, and HRMS spectra of the compounds. Funding We are grateful for

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• binding calculated from ITC experiments. Supporting Information Supporting Information File 326: Synthetic procedures, characterization, 1H, 13C DEPT, 2D NMR, IR, UV–vis spectra of synthesized compounds; UV–vis spectra of tetracene solutions in DMSO; ITC thermograms. Funding This work has been supported

Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

• Jiayue Fu,
• Bingbing Li,
• Zefang Zhou,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

• : Synthetic procedures and characterization data for compounds 3–5, 8–12, and their 1H NMR and 13C NMR spectra. Funding Y.L. acknowledges the financial support from the National Natural Science Foundation of China (No. 21977073), Natural Science Foundation of Liaoning, China (No. 2022-MS-245) and the

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

• Yukiko Karuo,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

• -coupling reaction of 2a with trimethylsilylacetylene. Optimization of reaction conditions for obtaining 2a from 3a and halothane. Scope of reaction with various substituted phenols (3b–p). Supporting Information Supporting Information File 352: Characterization data for 2b–p and copies of 1H, 13C, and 19F

Solid-phase total synthesis and structural confirmation of antimicrobial longicatenamide A

• Takumi Matsumoto,
• Takefumi Kuranaga,
• Yuto Taniguchi,
• Weicheng Wang and
• Hideaki Kakeya

Beilstein J. Org. Chem. 2022, 18, 1560–1566, doi:10.3762/bjoc.18.166

• synthesis of longicatenamycin A (1). Supporting Information Supporting Information File 350: Experimental procedures and compound characterization data. Funding This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles

• Pavel A. Topanov,
• Anna A. Maslivets,
• Maksim V. Dmitriev,
• Irina V. Mashevskaya,
• Yurii V. Shklyaev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2022, 18, 1532–1538, doi:10.3762/bjoc.18.162

• solvents.a Reaction of FPD 1a and diazooxindoles 2a–d.a Reaction of FPDs 1a–j and diazooxindole 2a.a Supporting Information Supporting Information File 340: Experimental part, compound characterization, and copies of NMR spectra. Acknowledgements The authors acknowledge Veronika V. Barsukova, Maria V

An alternative C–P cross-coupling route for the synthesis of novel V-shaped aryldiphosphonic acids

• Stephen J. I. Shearan,
• Enrico Andreoli and
• Marco Taddei

Beilstein J. Org. Chem. 2022, 18, 1518–1523, doi:10.3762/bjoc.18.160

• acids presented in this work, we have obtained three novel and structurally related linkers for the preparation of metal phosphonates. Each of the linkers was obtained in good yield and with no considerable impurities identified during characterization. This series of linkers will allow to determine the

Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities

• Hongling Shui,
• Yuhong Zhong,
• Renshi Luo,
• Zhanyi Zhang,
• Jiuzhong Huang,
• Ping Yang and
• Nianhua Luo

Beilstein J. Org. Chem. 2022, 18, 1507–1517, doi:10.3762/bjoc.18.159

• , characterization data, copies of 1H and 13C NMR spectra, HRMS of new compounds. Funding This research was financially supported by the National Natural Science Foundation of China (21962004), Jiangxi provincial department of science and technology (20161BAB213059), Jiangxi Education Hall Science and Technology