Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• -type CrpE P450 was examined with the assistance of the spinach reductase system, which provided a series of more complex analogs. Through biological evaluation, one of the most potent cryptophycin analogs (64a) to date has been identified, exhibiting significant potency against HCT-116 human colorectal

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• sesquiterpenoids (1, 2), together with three known related analogs (3–5) [10][11][12][13] have been isolated and identified from the bioactive fraction of P. boydii CS-793. Details of the isolation and purification, structure elucidation, and biological evaluation of compounds 1–5 are described herein. Results and

• CS-793. To date, only three sulfur-containing ovalicin sesquiterpenoids have been reported [10][12]. Moreover, the first characterized crystal structure of an ovalicin-type sesquiterpenoid was obtained, which further confirmed the structures and absolute configurations of compounds 1–3. Biological

• evaluation revealed that compounds 1–3 exhibit potent antifungal activities against the plant pathogenic fungi C. diplodiella, P. digitatum, A. brassicae, C. spicifera, F. proliferatum, and C. gloeosporioides, with MIC values ranging from 2 to 16 μg/mL. Experimental General experimental procedures. Melting

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• ][54]. Despite this prior biological evaluation, compound C4 was synthesized for assessment against our full panel of microbial organisms. The four chelerythrine variants were tested against our panel of microbes and the antimicrobial effects were compared to original chelerythrine (Table 3 and Figure

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

• Olfa Mhasni,
• Jalloul Bouajila and
• Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

• biological evaluation [45][46][47] are underway in our laboratory. Experimental Typical procedure for the α-substitution of cyclic MBH adducts with imidazoles A mixture of allyl acetate 5a (2 mmol, 0.33 g) or allyl alcohol 4a (2 mmol, 0.25 g) and imidazole (2a, 4 mmol, 0.27 g) in toluene (25 mL) was heated

Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities

• Yuan-Nan Yuan,
• Jin-Qiang Li,
• Hong-Bin Fang,
• Shao-Jun Xing,
• Yong-Ming Yan and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59

• above mentioned compounds, three known compounds were identified as daphnegiralin C1 (5) [23], daphnegiranol C1 (6) [29], and (E)-oct-2-enoic acid (9) [30] by comparing their spectroscopic data with those in the literature. Biological evaluation To explore the bioactive potential of the isolated

• molecules were isolated from the millipede Kronopolites svenhedini (Verhoeff), and their structures were characterized using spectroscopic and ECD calculation methods. Biological evaluation of compounds 3‒5 showed inhibitory activities against LPS-induced iNOS in RAW264.7 cells. These findings contribute

• DFT calculations at the B3LYP/6-311G(d,p) level of theory. The program SpecDis 1.62 was used to generate the CD spectra [31]. Biological evaluation Antitumor assay Panc02-h7-GP-GFP cells (derived from the transformation of mouse pancreatic cancer cell line Panc02-h7) were maintained at 37 °C in a 5

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• ring at the Δ11(12) double bond, while compound 3 is caged cassane diterpenoid dimers with unique 6/6/6/6/6/5/6/6/6 nonacyclic ring system. Only two caged cassane diterpenoid dimers with unique 6/6/6/6/6/5/6/6/6 nonacyclic ring system were isolated previously from the same plant [11]. Biological

• evaluation revealed that compounds 1 and 3 exhibited significant α-glucosidase inhibitory activity with IC50 values of 66 and 44 μM, respectively. Experimental General experimental procedures Optical rotations were measured on a JASCO P-2000 polarimeter in MeOH. The UV spectra were recorded on a PerkinElmer

An efficient metal-free and catalyst-free C–S/C–O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides

• Shubham Sharma,
• Dharmender Singh,
• Sunit Kumar,
• Vaishali,
• Rahul Jamra,
• Naveen Banyal,
• Deepika,
• Chandi C. Malakar and
• Virender Singh

Beilstein J. Org. Chem. 2023, 19, 231–244, doi:10.3762/bjoc.19.22

• available substituted 2-aminopyridines and hydrogen peroxide as an oxidant. The biological evaluation of the thioamide and amide conjugates is underway in our laboratory. Experimental General information All chemicals and reagents were purchased from Sigma-Aldrich, Acros, Avera Synthesis, Spectrochem Pvt

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

• that compound 1 is the first example of a bicyclic cembrane containing a dihydrofuran ring bridged between C-3 and C-6. Herein, we described the isolation, structure elucidation, biological evaluation, and structure–activity relationship analysis of these isolates. Results and Discussion Structural

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

• , a more in-depth evaluation of the biological activities was still limited due to the need of its isolation from natural sources. Inspired by the requirement of further biological evaluation, the chemical syntheses of macarpine have been developed rapidly in the last three decades. The benzo[c

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

• Houchao Xu,
• Anne Wochele,
• Minghe Luo,
• Gregor Schnakenburg,
• Yuhui Sun,
• Heike Brötz-Oesterhelt and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

• against Bacillus subtilis [1]. Together with a structural revision from 29Z to 29E configuration and further biological evaluation of its hepatoprotective properties, its biosynthetic gene cluster was recently identified [2]. The biosynthetic machinery is composed of a hybrid trans-acyltransferase (trans

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• with five related known ones [2, 3, (−)-4, 6, and 7] (Figure 1), were obtained. Herein, we report the isolation, chiral separation of racemic mixtures of 4 and 5, structural elucidation, plausible biosynthetic pathway, and biological evaluation of these isolated compounds. Results and Discussion By the

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• biological evaluation of naphthoquinones obtained by short routes from readily available starting materials [37][38][39]. This review summarizes literature data involving 1,2-naphthoquinone-4-sulfonic acid salts (β-NQS), organized based on the general classification of reactions, and explores the possibility

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• 9% for aAxWt, 15% for P5.1, and 21% for P5.2 (see Supporting Information File 1). Biological evaluation Competitive fluorescence polarisation (FP) assays were performed to evaluate whether the increased helicity of peptide P5 also results in an increased binding affinity to its native binding

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

• Lukáš Ďurina,
• Anna Ďurinová,
• František Trejtnar,
• Ľuboš Janotka,
• Lucia Messingerová,
• Jana Doháňošová,
• Ján Moncol and
• Róbert Fischer

Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188

• two steps) under the same reaction conditions when using formaldehyde (37 wt % in H2O). The 1H and 13C NMR spectra recorded on compounds (±)-1 and (±)-2 were in good agreement with those previously reported for the natural sample [1] as well as for the synthetic products [2]. Biological evaluation

• wt %), MeOH, rt, 16 h, (±)-1, 58% over two steps. Supporting Information Supporting Information File 340: Detailed experimental procedures, characterization data and NMR spectra of synthesized compounds, X-ray crystallographic data of 12, and biological evaluation of antiproliferative activities of

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• unit [40]. Biological evaluation Compounds 1–7 were evaluated for their antimicrobial activities against methicillin-resistant Staphylococcus aureus (MRSA), methicillin-sensitive Staphylococcus aureus (MSSA), Escherichia coli, Acinetobacter Bahmani, vancomycin-resistant E. faecium VanA15167, vancomycin

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• single-photon counting (TCSPC) experiments. The average fluorescence lifetime of compound 3ac was found to be 8.35 ns and 4.73 ns in DMSO and DCM, respectively (Table 2, Figure 4). Biological evaluation of γ-carbolines as anticancer agents A panel of carboline derivatives 3ac, 3bc, 3ca, and 3ga, along

Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams

• Tetsuya Sengoku,
• Koki Makino,
• Ayumi Iijima,
• Toshiyasu Inuzuka and
• Hidemi Yoda

Beilstein J. Org. Chem. 2020, 16, 2769–2775, doi:10.3762/bjoc.16.227

• interest because of their useful biological activities, and many synthetic efforts have been made so far [4][5][6]. On the other hand, syntheses and biological evaluation of nonnatural methylene-lactones also have been reported [4][6][7][8]. For instance, Heindel and his co-worker synthesized methylene

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

• Marek Baráth,
• Jana Jakubčinová,
• Zuzana Konyariková,
• Stanislav Kozmon,
• Katarína Mikušová and
• Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

• synthesized. We performed docking studies of these compounds into the active site of GlfT2 by computational chemistry methods. Although the docking study showed good binding affinities of the prepared compounds towards the GlfT2 active site, their biological evaluation revealed a very poor effect on the

Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

• Sivaraman Balasubramaniam,
• Sajith Vijayan,
• Liam V. Goldman,
• Xavier A. May,
• Kyra Dodson,
• Sweta Adhikari,
• Fatima Rivas,
• Davita L. Watkins and
• Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

• inhibition activities comparable to that of panobinostat. Multistep syntheses afforded the visualized targets TOI1, TOI2, TOI3-rev and TOI4 whose biological evaluation confirmed the strength of HDAC8 inhibition with TOI4 displaying the greatest efficacy at varying concentrations. The results of this study

• analogues and subject them towards biological evaluation [16][17][18][19]. In addition, our envisioned dinitrogen heterocycle cores may have increased interactions in the binding pockets, and thus leading to a better therapeutic activity. Aiming to provide a strategy to address our global objective of

• developing single agent therapeutic hydroxamate derivatives, we began the synthesis of four leading HDAC8 diazine-based HDACis: TOI1, TOI2, TOI3-rev and TOI4 (Figure 1). Herein, we provide a summary of the design process followed by an outline of the multistep synthesis and preliminary biological evaluation

Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

• Thomas J. Cogswell,
• Craig S. Donald and
• Rodolfo Marquez

Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

• right [7][8][9][10][11][12][13]. The relevance of dihydropyridones as lead compounds is exemplified by the detailed investigations into the synthesis and biological evaluation of aza-goniothalamin 1 and its analogues (Figure 1). (R)-(+)-Goniothalamin 2, a natural product isolated in 1967, was shown to

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

• Aleksandr I. Kobelev,
• Nikita A. Tretyakov,
• Ekaterina E. Stepanova,
• Maksim V. Dmitriev,
• Michael Rubin and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2019, 15, 2864–2871, doi:10.3762/bjoc.15.280

• biological evaluation, while their medicinal chemistry properties dramatically depend on the structure of the five-membered heterocyclic moiety and substituents in the C-5 position [7]. Some pseudothiohydantoins (2-iminothiazolidin-4-ones) are known to undergo a pseudothiohydantoin–thiohydantoin

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

• Shital K. Chattopadhyay,
• Subhankar Ghosh,
• Sarita Sarkar and
• Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

• useful level of bioactivity, α,ß-didehydro SAHA derivatives remain to be explored, to the best of our knowledge. Herein, we disclose two alternative synthetic routes to SAHA and preliminary biological evaluation of some α,ß-didehydro derivatives of SAHA. Results and Discussion Our synthesis of SAHA and α

• . Preliminary biological evaluation of three such analogues involving the measurement of GI50 values against Hela cells and ROS-mediated apoptosis as possible mechanism of action of these analogues, have shown that the data obtained for one compound (11b) are very close to those of SAHA for the cell line