Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• industry: a review” by N. Morini-Crini; S. Fourmentin; É. Fenyvesi; E. Lichtfouse; G. Torri; M. Fourmentin; G. Crini, Environmental Chemistry Letters, Vol. 19, pp 2581–2617, 2021), Copyright 2021 Springer Nature. Journal home page: https://www.springer.com/journal/10311. This content is not subject to CC

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• , volatile solvents, hard conditions, and/or difficult purifications. However, green chemistry has become a crucial sub-discipline in the field of chemistry and the chemical industry is giving major priority to sustainable processes. Since a few years, deep eutectic solvents (DES) are considered as a

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• exhibit a variety of biological activity. Their application is known in pharmacy [1][2][3][4] and agro-industry [5][6][7][8]. Especially such compounds are used to protect plants from insects and weeds (Figure 1). Thus, pinoxaden is a commercially available inhibitor of acetyl-CoA carboxylase and affects

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

• Damiano Diprima,
• Hannes Gemoets,
• Stefano Bonciolini and
• Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

• byproducts, and increased efficiency in industrial processes. As such, this field of research is of great importance and interest to both academia and industry. This work showcases a sustainable and catalyst-free oxidation method for heteroatoms (e.g., S, P, and Se) using only air, water and light. An

• flow using the HANU flow reactor, indicating scalability and improving safety. Keywords: catalyst-free; flow chemistry; oxygen; photochemistry; sustainable oxidation; Introduction Oxidation reactions are widely used in the chemical industry, but are often problematic due to challenges with

• of heteroatoms, making them a promising alternative to traditional oxidants in the chemical industry [9]. Our interest in sustainable oxidation methodologies led us to study the selective oxidation of various heteroatoms to their corresponding oxides, including sulfides to sulfoxides, phosphine to

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

• context of deeply reductive reactions, dissolving alkali metal conditions have remained the most commonly employed both in academia and industry for over a century and even to date continue to be used despite their hazards, poor selectivity and chemical waste [7][8][9][10]. Nowadays, excellent alternative

• appropriate in certain contexts of application. Broadly speaking, it can be concluded that carrying out reactions with conPET, both in academia and industry, has a lower barrier of accessibility due to more intuitive/standardized reactor setups. Essentially, the reactor setup can be identical to standard

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• , Tokyo, Japan). Plant material The resinous wood of Aquilaria sinensis was purchased from Hainan Xiangshu Agarwood Industry Groud Co., Ltd., July 2018. The material was identified by the Gansu Institute for Drug Control, and a voucher specimen (CHYX0642) was deposited at School of Pharmaceutical Sciences

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• products. Keywords: amino acids; asymmetric catalysis; multicomponent reaction; palladium catalysis; Petasis reaction; sulfonamides; Introduction α-Amino acids play a crucial role in every aspect of our human life [1]. They are important synthetic intermediates in the chemical industry and used for the

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• David I. H. Maier Barend C. B. Bezuidenhoudt Charlene Marais Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa 10.3762/bjoc.19.51 Abstract The dibenzo[b,f]azepine skeleton is important in the pharmaceutical industry, not only in terms of existing

Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles

• Deepak Singh,
• Shyamal Pramanik and
• Soumitra Maity

Beilstein J. Org. Chem. 2023, 19, 666–673, doi:10.3762/bjoc.19.48

• from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C–H functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

• Grédy Kiala Kinkutu,
• Catherine Louis,
• Myriam Roy,
• Juliette Blanchard and
• Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

• of the development of a sustainable chemical industry [1][2][3][4]. Furfurals, which are versatile platform molecules derived from renewable lignocellulose present in agricultural wastes [5][6][7][8], have proven to be of great importance for the preparation of value-added chemicals, biofuels, as

• temperature). Thus, despite the synthetic interest of the molecules that can be obtained, transfers to industry are difficult. In order to circumvent this drawback, we considered transposing these batch reactions to a flow chemistry process. In recent years, the use of continuous flow chemistry in organic

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• testing; Introduction Asymmetric synthesis of functionalized amino acids is a subject of intense research because these compounds are of great demand for pharmaceutical industry, health care, and food production [1][2][3]. Various approaches to enantiomerically enriched amino acids have been developed

Total synthesis: an enabling science

• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

• (biomimetic synthesis) [14]. In addition, total syntheses have also been achieved with enzymes, strengthening the links to biology [15]. Total synthesis is not limited to academic laboratories but rather also pursued in industry, where a particular efficiency and economy of tasks is of paramount importance

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

• Louis Monsigny,
• Floriane Doche and
• Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

• pharmaceuticals and 30–40% of agrochemicals [3][4][5] contain at least one fluorine atom. Because of the exceptional features of fluorinated derivatives, tremendous developments and discoveries have been made in this blossoming research area, with a high interest for fundamental research as well as the industry

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

• processes in the pharmaceutical industry [1][27]. During continuous flow reactions, the target molecules can be produced with better purity, selectivity and in higher yields, as well as in consistent quality due to the precise parameter control, low volume ratio and small quantities. The temperature control

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

• similarity factor (f2) were computed using a method outlined in the Guidance for Industry from the FDA's Center for Drug Evaluation and Research (CDER) [77]. These two factors can be calculated mathematically by the following equations [78]. R and T are the percentage dissolved of the reference and test

Modern flow chemistry – prospect and advantage

• Philipp Heretsch

Beilstein J. Org. Chem. 2023, 19, 33–35, doi:10.3762/bjoc.19.3

• stage in the last decades [1]. Originating from the petrochemical industry, where it enabled high productivity and scalability even for the most standard processes of heating, cracking, and refining of crude oil to bulk chemicals [2], it has since entered the production of pharmaceuticals and other fine

• - and postrun fractions are discarded [6], leading to loss of reagent and substrate as well as to increased waste. This is even less tolerable when small quantities of precious intermediates from multistep routes are to be employed, as is typically the case in projects of the pharmaceutical industry and

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

• pharmaceutical industry for many decades. However, the complexation of APIs with cyclodextrins (cyclic oligosaccharides) resulting in the formation of inclusion complexes, has proven to be a versatile technology for overcoming not only the poor aqueous solubility of APIs, but also unfavourable properties such as

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• and mass transfer, improved safety and scalability as well as the potential of reaction telescoping and automation [1][2]. Consequently, researchers from academia and the fine chemical industry have established flow technology as a complementary and oftentimes superior approach to traditional batch

• routinely employed in both industry and academia, examples of such systems integrated in continuous flow reactions are scarce. Recently, two protocols were reported that use an Advion puriFlash® 5.250 system for continuous purifications [37][38]. The puriFlash® system is an automated liquid chromatography

• expected that future refinements will lead to more robust and frequently exploited technologies. Inline extractions/separations Inline extractions are the most common type of workup performed in both industry and academia. They can be divided into two groups: those performed with semipermeable membranes

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

• Biodiversity Genomics (LOEWE TBG) and the German Chemical Industry Association. FB acknowledges funding from a Kekulé Fellowship of the German Chemical Industry Association.

Functionalization of imidazole N-oxide: a recent discovery in organic transformations

• Koustav Singha,
• Imran Habib and
• Mossaraf Hossain

Beilstein J. Org. Chem. 2022, 18, 1575–1588, doi:10.3762/bjoc.18.168

• Koustav Singha Imran Habib Mossaraf Hossain Synthetic Organic Research Laboratory, UGC-HRDC (Chemistry), University of North Bengal, Siliguri, Darjeeling, 734013, India 10.3762/bjoc.18.168 Abstract Nowadays heterocyclic compounds are widely used in medicinal chemistry and industry to develop life

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

• Foundation, The Tokyo Biochemical Research Foundation, and the foundation of Tokyo Chemical Industry to T.K. are greatly appreciated.

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• sourced from the NatureBank open access compound library, is also reported. Results and Discussion While the unique NatureBank HTS-compatible natural product screening libraries (>21K extracts and >105K fractions) [14] have been regenerated for biodiscovery collaborations with industry and academia over

One-pot synthesis of 2-arylated and 2-alkylated benzoxazoles and benzimidazoles based on triphenylbismuth dichloride-promoted desulfurization of thioamides

• Arisu Koyanagi,
• Yuki Murata,
• Shiori Hayakawa,
• Mio Matsumura and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 1479–1487, doi:10.3762/bjoc.18.155

• benzazoles containing oxazole and imidazole skeletons are the most commonly used scaffolds [1][2][3][4][5]. Therefore, it is crucial for the drug industry to develop methods for their syntheses [1][2][4][6]. For example, conventional benzoxazole synthesis methods involve the condensation of 2-aminophenol

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• that, in many countries, academic research in medicinal chemistry should be more funded, especially in the therapeutic area neglected by the industry. At the least, such funds would provide the intensive to secure series of hopefully relevant chemical entities which appears to often lack when

• , medicinal chemistry is often not being considered as a true academic research domain. In many countries, the decision to delegate this aspect of drug discovery to the industry was instrumental in the policy choices made by their public funding agencies. However, at least in the research domains of anti

• pharmaceutical industry which certainly owe some of its origin to the academic world [34][35][36][37]. This perspective will not describe the true chemical challenges as well as the many environmental issues surrounding this last problem. All these are actually well described in books [38][39][40][41][42][43