Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• , Don Young Road, Brisbane, 4111, Australia 10.3762/bjoc.20.266 Abstract The marine sponge Suberea ianthelliformis was investigated for new chemistry after the recent discovery that polyamines ianthelliformisamines A–C (1–3) – originally sourced from this Australian sponge – act as Pseudomonas

• activity against both Pseudomonas aeruginosa and Staphylococcus aureus, has contributed to a surge in the interest of polyamines as new antibacterial leads [6]. To date the total synthesis of ianthelliformisamines A–C (1–3) has been described [7] and numerous synthetically related analogues have been

• supported the important role that the polyamine chain length plays in antibacterial activity. Of note, increasing research providing structure–activity relationship analyses shows that polyamines (including spermine) are bacterial membrane disruptors and are beneficial in enhancing activity of known

Total synthesis of ent-pavettamine

• Memory Zimuwandeyi,
• Manuel A. Fernandes,
• Amanda L. Rousseau and
• Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

• 1995, was previously identified as a polyamine with C2 symmetry and a 1,3-syn-diol moiety on a C10 carbon backbone – one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the

• ; pavettamine; polyamine; Introduction The identification and first reported synthesis of pavettamine (1) heralded the arrival of a novel and uniquely hydroxylated polyamine (PA) (Figure 1) [1]. In general, polyamines are described as aliphatic organic compounds with two or more primary amine substituents

• , connected by one or more unsubstituted methylene linkages, within their structure [2]. The interest in polyamines arises from the diverse roles and functions they play in biological systems [3][4]; for example, as stabilizers of RNA and DNA, secondary messengers, nutrients, antioxidants, growth factors, and

Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• and plant tissues. Many ptomaines are polyamines (putrescine, cadaverine), but others are not (indole, scatole). The name ptomaine (Leichengift in German) has disappeared from the modern lingo of organic chemistry because of the heterogeneous nature of these compounds. The formation of ptomaines was

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• Group, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Łódź, Poland 10.3762/bjoc.17.50 Abstract Amino- and polyaminophthalazinones were synthesized by the palladium‐catalyzed amination (alkyl- and arylamines, polyamines) of 4-bromophthalazinones in good yields. The coordinating

• Information File 1). In the next step, the bromolactams 3 were subjected to a thermal palladium cross-coupling reaction with various amines and polyamines. To optimize the reaction conditions, we investigated the reaction of 4-bromo-2-methylphthalazin-1(2H)-one (3a) with morpholine as the model substrates

• –amine system (Figure 2), facilitating the oxidative addition of the bromolactam 3a and is the crucial step in the amination procedure of 4-bromophthalazinones [40]. Based on the results of our initial studies, we next examined the reaction scope of the bromolactams 3 with various amines and polyamines

Fabclavine diversity in Xenorhabdus bacteria

• Sebastian L. Wenski,
• Harun Cimen,
• Natalie Berghaus,
• Sebastian W. Fuchs,
• Selcuk Hazir and
• Helge B. Bode

Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84

• Information File 1). In these strains, additional derivatives with polyamines made of five amine units were identified (9–12, Table 1 and Figures S13 and S17, Supporting Information File 1). In X. hominickii, only derivatives with polyamines made of five amine units were identified, but none with less (Table

• set of fabclavines with unique features, such as polyamines with different lengths or an additional polyketide unit. Considering the fabclavine biosynthesis in X. szentirmaii, the responsible components for such a chemical variety seem to be the following: The first is a lowered substrate specificity

Polyaminoazide mixtures for the synthesis of pH-responsive calixarene nanosponges

• Antonella Di Vincenzo,
• Antonio Palumbo Piccionello,
• Alberto Spinella,
• Delia Chillura Martino,
• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2019, 15, 633–641, doi:10.3762/bjoc.15.59

• , considering that NSs possess anyway a highly disordered structure, we reasoned that the use of a pure product as the reticulating agent would not have been a stringent requirement. So, we decided to react the aforementioned polyamines 1 and 2, with the crude mixture described in Scheme 3. After having

• I (red) and mixture II (blue). FTIR spectra (nujol) of Ca (red), CaNS-I (blue) and CaNS-II (green). CP-MAS NMR spectra of CaNSs. Structures of guests 6–15. Synthesis of the propargyloxy calixarene Ca. Synthesis of polyaminoazides from polyamines. Reaction of 1,3-dibromopropane (4) with sodium azide

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

• Christian Schütz and
• Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

• deprivation, pH, anaerobiosis, as well as biocides, polyamines, cations and carbon sources could also act as external triggers leading to adaptive resistance. The common effect of these stimuli seems to be an alteration in expression patterns ultimately impacting, e.g., efflux pump or enzymatic activity, as

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• interactions between the adenine groups of the nucleotide and the receptor’s aromatic moieties [9] can additionally contribute to the complex stability and binding selectivity. Polyammoniums mimic the biologically important acyclic polyamines such as putrescine, spermidine, and spermine, which have strong

• groups in the 1H NMR spectra fully corresponded to the proposed structures of 9 and 11 (Supporting Information File 1, Figures S9, S10, S13, and S14). The polyamines 10a,b and 12a,b were obtained in high yields after BOC deprotection with HCl in dioxane as water-soluble di- and tetrahydrochlorides

Phosphodiester models for cleavage of nucleic acids

• Satu Mikkola,
• Tuomas Lönnberg and
• Harri Lönnberg

Beilstein J. Org. Chem. 2018, 14, 803–837, doi:10.3762/bjoc.14.68

• second-order rate constant for the ethylenediamine-catalyzed cleavage of ApA has been reported to be 1.2∙10−6 L mol−1 s−1 at pH 8 and 50 °C [83]. Cyclic polyamines are somewhat better catalysts (Figure 9). The tetracation of 1,4,16,19-tetraoxa-7,10,13,22,25,28-hexaazacyclotriacontane (9) cleaves ApA

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• ed. 18, 90128 Palermo, Italy 10.3762/bjoc.13.271 Abstract Three polyaminocyclodextrin materials, obtained by direct reaction between heptakis(6-deoxy-6-iodo)-β-cyclodextrin and the proper linear polyamines, were investigated for their binding properties, in order to assess their potential

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• ][21][22][23][24][25][26][27][28][29][30][31][32][33][34], have not been prepared so far. In the present work, we focused on the development of a general approach to tertiary amines and polyamines bearing several hydrazonomethyl arms at the nitrogen atom(s). To achieve this goal, we suggested a

• our knowledge, there is only one report on the formation of bishydrazones as undesirable products in reactions of some primary amines with N-tosylhydrazone of o-bromophenacyl bromide [50]. We suppose that extension of the scope of azoalkene–amine coupling to ammonia, primary amines and polyamines

• ). Similarly, the reaction with a secondary amine (morpholine) according to this procedure provided the monoalkylated adduct 6 in good yield. Importantly, secondary polyamines could be exhaustively alkylated with chloroacetone hydrazone 1a demonstrating the efficiency of our approach for the synthesis of

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• of the CD scaffold with two different linkers (both polyamines) and then on the coupling of the terminal amino group of the linkers with rhodamine B. The coupling conditions were slightly different from those reported by Harada [14]. The solvent was a mixture of pyridine and DMF, the activating

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

• Svetlana P. Panchenko,
• Alexei D. Averin,
• Maksim V. Anokhin,
• Olga A. Maloshitskaya and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

• polyamines such as putrescine, cadaverine, spermine, spermidine and their homologues is described. Aryl iodides bearing electron-donating and electron-withdrawing groups have been employed in the study. The CuI/2-(isobutyryl)cyclohexanone/DMF catalytic system has found to be more efficient in the diarylation

• of diamines and spermine while the CuI/L-proline/EtCN system proved to be preferable for the diarylation of other tri- and tetraamines like spermidine, norspermidine and norspermine. Keywords: amination; aryl amines; aryl iodides; copper catalysis; polyamines; Introduction Natural diamines and

• polyamines like putrescine (butane-1,4-diamine), spermidine (N1-(3-aminopropyl)butane-1,4-diamine) and spermine (N1,N1'-(butane-1,4-diyl)dipropane-1,3-diamine) are biologically active compounds which play crucial roles in the processes of cell proliferation, apoptosis and adaptation to stress impacts. The

Exploring monovalent and multivalent peptides for the inhibition of FBP21-tWW

• Lisa Maria Henning,
• Sumati Bhatia,
• Miriam Bertazzon,
• Michaela Marczynke,
• Oliver Seitz,
• Rudolf Volkmer,
• Rainer Haag and
• Christian Freund

Beilstein J. Org. Chem. 2015, 11, 701–706, doi:10.3762/bjoc.11.80

• spliceosome, where the optimization of a peptide ligand by phage screening and subsequent multivalent display on a dendritic polymer is combined to create higher affinity binders with the potential to be used in cellular studies. Dendritic polyamines such as polyglycerol amine [7][8], polyethyleneimine [9][10

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with

• either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed

• azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described. Keywords: click chemistry; glycans; peptoids; polyalkynes; polyamines; solid-phase chemistry; Introduction To date, oligosaccharides have gained more and more interest as potential drugs in

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• variety of polymers, e.g., with epoxy, polyurethane (Figure 7), and polyurea, or based on synthetic polyamines, polythiourea, crosslinked starch, dextran or polyethylene imine [116]. Therefore, the functionality can be directly implemented in the capsules by using an excess of one of the monomers, or by

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids

• Teresa Borowiak,
• Grzegorz Dutkiewicz,
• Maciej Kubicki,
• Marek Pietraszkiewicz,
• Agnieszka Gil and
• Rainer Mattes

Beilstein J. Org. Chem. 2005, 1, No. 16, doi:10.1186/1860-5397-1-16

• adduct of; Hydrogen bonding; Molecular recognition; Two-dimensional supramolecular frameworks; Introduction Macrocyclic polyamines are well-known to participate in molecular recognition phenomena with different kinds of substrates such as organic and inorganic anions or neutral molecules[1] that give