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Search for "isostere" in Full Text gives 15 result(s) in Beilstein Journal of Organic Chemistry.

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

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  • showed strong efficacy against commercially important weeds, in particular resistant ryegrass (LOLSS_R), combined with promising crop safety. In our view, these results underline that chemical innovation using isostere concepts and addressing unusual structural features is a useful tool to broaden the
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Published 01 Mar 2024

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

  • Yumei Wang,
  • Guangzhu Wang,
  • Yanping Zhu and
  • Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

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  • isostere of polar functional groups [5][6]. Chiral indoline is an important member of the class of nitrogen-containing heterocyclic compounds that often exhibits various pharmaceutical activities and exists in many natural products [7][8]. The enantioselective synthesis of chiral indolines has received
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Published 01 Feb 2024

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

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  • mercaptopurine (Figure 1), containing an intracyclic thioamide group, are antagonists of purine bases and are well known as cytostatic drugs [13]. The thioamide group as an amide isostere is used in medical chemistry to increase thermal and proteolytic stability and improve the pharmacokinetic properties of
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Published 08 Aug 2023

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

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  • an aryl or alkynyl unit [16][17][18][19][20][21][22]. In a biological context, the fluoroalkenyl motif could be incorporated into peptides with the expectation that the fluoroalkenyl unit could serve as a peptide isostere and prevent unexpected hydrolysis of these compounds. Recent studies have shown
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Published 21 Nov 2022

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

  • Ryan M. Alam and
  • John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

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  • electrophiles, while maintaining a high degree of N-1 regioselectivity. Keywords: indazole; N-alkylation; regioselective; sodium hydride; tetrahydrofuran; Introduction Indazole (benzo[c]pyrazole) is an aromatic bicyclic heterocycle and can be viewed as a (bio)isostere of indole [1]. While only a few naturally
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Published 02 Aug 2021

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

  • Christopher Liczner,
  • Kieran Duke,
  • Gabrielle Juneau,
  • Martin Egli and
  • Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

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Published 28 Apr 2021

Synthetic strategies of phosphonodepsipeptides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

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  • (12b) and (R)-2-hydroxyglutaric acid dimethyl ester (128) with BOP as coupling reagent, followed by hydrogenolysis and coupling with 2-(2-phthalimidoethoxy)acetic acid (130). The amide bond between ʟ-Ala and ᴅ-Glu was replaced by a phosphonate isostere, giving the phosphonodepsipeptide 131 (Scheme 22
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Published 16 Feb 2021

Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups

  • Benjamin Jeffries,
  • Zhong Wang,
  • Robert I. Troup,
  • Anaïs Goupille,
  • Jean-Yves Le Questel,
  • Charlene Fallan,
  • James S. Scott,
  • Elisabetta Chiarparin,
  • Jérôme Graton and
  • Bruno Linclau

Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182

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  • isopropyl substituent led to larger lipophilicity modulation compared to fluorination of the cyclopropyl substituent. Keywords: aliphatic fluorination; cyclopropane; isopropyl; isostere; lipophilicity; oxetane; Introduction The introduction of small alkyl groups onto bioactive compounds as space filling
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Published 02 Sep 2020

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

  • Daniela Imperio,
  • Erika Del Grosso,
  • Silvia Fallarini,
  • Grazia Lombardi and
  • Luigi Panza

Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

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  • and biological behavior of novel derivatives containing this functional group at the anomeric position, giving rise to an isostere analogue able to mimic the monosaccharide (see Figure 1). Results and Discussion In the present paper the synthesis of two analogues bearing a boron atom at the anomeric
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Published 19 Jun 2019

Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

  • Juan V. Alegre-Requena,
  • Marleen Häring,
  • Isaac G. Sonsona,
  • Alex Abramov,
  • Eugenia Marqués-López,
  • Raquel P. Herrera and
  • David Díaz Díaz

Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

Graphical Abstract
  • properties of supramolecular gels [33]. Specifically, we exchanged the amide group of N-stearoyl-L-glutamic acid (1, Figure 1), a known LMW gelator [34], by its non-classical isostere [35][36] 1,4-disubstituted 1,2,3-triazole 2 (Figure 1). This approach enabled us to fine-tuning the gelation capacity and the
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Published 06 Aug 2018

Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases

  • Svetlana O. Kasatkina,
  • Ekaterina E. Stepanova,
  • Maksim V. Dmitriev,
  • Ivan G. Mokrushin and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2018, 14, 1734–1742, doi:10.3762/bjoc.14.147

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  • ; Introduction Quinoxaline is a 4-aza isostere of quinoline, which rarely occurs in structures of natural products. Its derivatives are gaining popularity in medicinal chemistry and pharmacology because many of them exhibit various biological activities [1][2]. Quinoxaline-based 6/6/6-angularly fused scaffolds
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Published 11 Jul 2018

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

  • Myriam Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

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  • tertiary and quaternary structures. To have a good amide bond isostere, these different aspects should be reproduced, which is mostly the case with the monofluoroalkene moiety [8]. The monofluoroalkene is a rigid molecule as it possesses a double bond. Furthermore, the fluorine atom bears a partial
  • )-monofluoroalkene is an analogue of the s-trans amide bond, while the (E)-monofluoroalkene mimics the s-cis form. Considering those favourable properties, monofluoroalkenes constitute an interesting amide bond isostere, thus many researches have investigated their synthesis and application [16][17][18][19][20][21
  • free alcohol which was oxidized to provide the N-protected dipeptide isostere 9. Some limitations were observed towards the compatibility of the N-protecting groups and in particular, N-tert-butoxycarbonyl-protected amines were not compatible with this methodology. Xaa-ψ[CF=CH]-Gly To access Xaa-ψ[CF
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Published 12 Dec 2017

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

  • Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

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  • -Sanders Model for π–π stacking from 1990 [4]. (d) Kool’s nonpolar isostere of thymidine from 1995 [5].(e) Gellman’s model for π–π stacking in aqueous solution [6]. (a) Model β-hairpin for investigation of aromatic interactions. (b) Examples of noncovalent interactions studied, from weakest to strongest
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Published 17 Aug 2016

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

  • Meriem Smadhi,
  • Sophie de Bentzmann,
  • Anne Imberty,
  • Marc Gingras,
  • Raoudha Abderrahim and
  • Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

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  • -phase chromatography. Methyl 6-azido-6-deoxy-α-D-mannoside was similarly coupled as a less expensive isostere of L-fucose [41]. The tris 6-C-(6-deoxy-D-mannosyl) cluster 15 was thus obtained in 47% yield. The cycloaddition conditions were optimized using 3.3 equiv of glycosyl azide [39] and one
  • . The 6-deoxymannose isostere 15 was not tested, in view of the low affinity of the β-fucose epitopes. These clusters thus represent a readily accessible, highly soluble, and convenient tool for the investigation of the role of lecA and lecB in the formation of biofilms by Pseudomonas aeruginosa
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Published 25 Aug 2014

Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds

  • G. K. Surya Prakash,
  • Xiaoming Zhao,
  • Sujith Chacko,
  • Fang Wang,
  • Habiba Vaghoo and
  • George A. Olah

Beilstein J. Org. Chem. 2008, 4, No. 17, doi:10.3762/bjoc.4.17

Graphical Abstract
  • propynoates at room temperature to yield the corresponding adducts in moderate to excellent yields. Background Compounds with a monofluoromethyl moiety are of great importance with regards to isostere-based drug design [1][2][3][4]. Consequently, synthesis of new functionalized α-monofluorine-substituted
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Published 21 May 2008
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