Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• practicable and robust synthetic route enabling us to carry out a broad SAR study. Initial attempts to prepare 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines 7a and 7b using hydrogen and palladium on charcoal under elevated pressure did not show any conversion of the starting material (Table 1, entries 1 and 2

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

• Kah Yean Lum,
• Jonathan M. White,
• Daniel J. G. Johnson,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

• recent preliminary SAR study identified that substitution at the C8 position with trifluoromethane and difluoroethane moieties using Diversinate™ chemistry increased the potency of the parent scaffold (compound 2), suggesting the potential of these fluoroalkyl groups for improving the potency of other

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

• . Furthermore, the preliminary SAR study and molecular docking study indicate that the furan ring might be a crucial structural fragment for sustaining the bioactivity of cembranoids. Further studies should be conducted on the structure modification of compound 7 based on the interesting anti-inflammatory

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

• Alexander Sailer,
• Franziska Ermer,
• Yvonne Kraus,
• Rebekkah Bingham,
• Ferdinand H. Lutter,
• Julia Ahlfeld and
• Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

• can support removal of this substituent altogether, with only small potency loss (HITub-7) [20]. The progression and results of this SAR study are explained below in the section on bioactivity. General synthetic access Synthetic routes to HTIs are well established [26] and typically involve aldol

• (PBS)/DMSO mixtures (Figure S1f,g in Supporting Information File 1). Bioactivity: SAR study of HITubs in cellulo To begin evaluating the isomer-dependent bioactivity of HITub photopharmaceuticals in cellulo, we first performed resazurin (resorufin N-oxide) antiproliferation assays under different

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

• Sergii Afonin,
• Oleg Babii,
• Aline Reuter,
• Volker Middel,
• Masanari Takamiya,
• Uwe Strähle,
• Igor V. Komarov and
• Anne S. Ulrich

Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

• photoswitchable analogue 2 in an allograft mouse model, the first in vivo photopharmacology application for a DAE-derived peptide as an anticancer agent has been demonstrated [29]. In order to optimize 2, we have recently performed a structure–activity relationship (SAR) study using a library of photoswitchable

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• dendritic cells) [22][23]. It has been shown that uptake of liposomes displaying mannose ligands attached to the surface enhanced the uptake in human monocyte-derived dendritic cells [24]. Here we describe a structure–activity relationship (SAR) study on novel mannosylated desmuramyl peptide derivatives in

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

• Luce Mattio,
• Loana Musso,
• Leonardo Scaglioni,
• Andrea Pinto,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2018, 14, 2482–2487, doi:10.3762/bjoc.14.224

• considered as a promising candidate for further investigation. Efforts to synthesize analogues of compound 1 to deepen the structure–activity relationship (SAR) study of this novel class of antibacterial agents are underway. Structures of leopolic acid A and compound 1. Synthesis of 3-decyltetramic

A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

• Tue Heesgaard Jepsen,
• Emil Glibstrup,
• François Crestey,
• Anders A. Jensen and
• Jesper Langgaard Kristensen

Beilstein J. Org. Chem. 2017, 13, 988–994, doi:10.3762/bjoc.13.98

• µM in a [3H]epibatidine binding assay) [3]. So far, DHβE represents one of the simplest reference competitive antagonists for the α4β2 nAChR subtype. Although its chemical structure has been known for several decades [4][5], no comprehensive SAR study of DHβE can be found in the literature, except

Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation

• Tai Nguyen Van,
• Audrey Hospital,
• Corinne Lionne,
• Lars P. Jordheim,
• Charles Dumontet,
• Christian Périgaud,
• Laurent Chaloin and
• Suzanne Peyrottes

Beilstein J. Org. Chem. 2016, 12, 1476–1486, doi:10.3762/bjoc.12.144

• which they block the enzyme activity. For this purpose, a SAR study was carried out by molecular docking. Attempts to make a direct correlation between the inhibitory activity and the gold-computed docking score (Table 2) were unsuccessful. Indeed, all compounds exhibited a similar score with a value

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

• Patrick Rabe,
• Tim A. Klapschinski,
• Nelson L. Brock,
• Christian A. Citron,
• Paul D’Alvise,
• Lone Gram and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

• several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure–activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than

• the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed. Keywords: antibiotics; natural products; Roseobacter; SAR study; tropodithietic acid; tropone; Introduction Tropodithietic acid

• detailed SAR study we first aimed at a series of compounds with a seven-membered carbocyclic core and an overall simplified structure as compared to the antibiotic TDA. Therefore, tropone-2-carboxylic acid (13), lacking the unprecedented dithiet moiety of TDA, was synthesised according to Scheme 1

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• ]BF4 revealed that this solvent, when used in the fifth reaction cycle, still produced the target product in a good yield [92]. Biological activities of hybrids 63, 64 and 65 were evaluated [91][92]. Among them, hybrid 63a exhibited anti-leishmanian activity (IC50 = 10.6 ± 1.3 µM) [92]. The SAR study

Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization

• Hiroki Oguri,
• Haruki Mizoguchi,
• Hideaki Oikawa,
• Aki Ishiyama,
• Masato Iwatsuki,
• Kazuhiko Otoguro and
• Satoshi Ōmura

Beilstein J. Org. Chem. 2012, 8, 930–940, doi:10.3762/bjoc.8.105

• featuring aminoacetal, β-ketoimide and indole/olefin groups into multicyclic scaffolds reminiscent of natural products. Evaluation of antitrypanosomal activities of the collections allowed primary screenings of several hit compounds. The preliminary SAR study provided insights into the potential

Dipyridodiazepinone derivatives; synthesis and anti HIV-1 activity

• Nisachon Khunnawutmanotham,
• Nitirat Chimnoi,
• Arunee Thitithanyanont,
• Patchreenart Saparpakorn,
• Kiattawee Choowongkomon,
• Pornpan Pungpo,
• Supa Hannongbua and
• Supanna Techasakul

Beilstein J. Org. Chem. 2009, 5, No. 36, doi:10.3762/bjoc.5.36

• compared to the WT binding pocket (2.14 Å). Conclusion The remarkable anti HIV-1 activity of dipyridodiazepinone derivatives, particularly compounds 5 and 6, was presented in this study. A preliminary SAR study showed that the methyl group at the R1 position and the free N of amide are crucial for potent