Search results

Search for "lipophilicity" in Full Text gives 123 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

Graphical Abstract
  • ]pyridine 7b had a higher water solubility of 173 mg/L and a lower LogP of 1.59 (pH 2.3). However, the lipophilicity of the new 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines was highly dependent on the substituents. For example, the brominated analogs 13b and 13c showed considerably higher LogP values of 2.88
PDF
Album
Supp Info
Full Research Paper
Published 01 Mar 2024

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

  • Alexander S. Hampton,
  • David R. W. Hodgson,
  • Graham McDougald,
  • Linhua Wang and
  • Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

Graphical Abstract
  • present in many agrochemical and pharmaceutical products owing to the beneficial properties imparted such as increased metabolic stability, lipophilicity and bioavailability of the bioactive entity [1][2][3]. In 2018, 30% of FDA approved drugs contained at least one fluorine atom, with an average of 2.7
PDF
Album
Supp Info
Full Research Paper
Published 28 Feb 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

Graphical Abstract
  • excellent yield and enantioselectivity. Keywords: asymmetric organocatalysis; chiral Brønsted acid; 3,3-difluoroindoline; Hantzsch ester; transfer hydrogenation; Introduction The introduction of fluoro atoms into organic molecules can alter their lipophilicity, solubility, metabolic stability, and
PDF
Album
Supp Info
Letter
Published 01 Feb 2024

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF3: the case of alkyne hydration. Chemistry vs electrochemistry

  • Marta David,
  • Elisa Galli,
  • Richard C. D. Brown,
  • Marta Feroci,
  • Fabrizio Vetica and
  • Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

Graphical Abstract
  • ring (Table 3, entries 1–5). Although BMIm-BF4 gave a slightly higher yield than that obtained with EMIm-BF4, the general trend suggests that probably the increase in the lipophilicity of the ILs impairs the reaction, hindering the attack of water to the triple bond. Furthermore, the reaction in BDMIm
PDF
Album
Supp Info
Full Research Paper
Published 28 Dec 2023

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

  • Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

Graphical Abstract
  • lipophilicity and metabolic stability compared to nonfluorinated compounds [1][2][3][4][5]. At present, about 300 drug molecules and over 400 pesticides on the market contain at least one fluorine atom [6][7]. Therefore, the development of novel and effective synthetic methodologies for the synthesis of
PDF
Album
Review
Published 15 Nov 2023

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

Graphical Abstract
PDF
Album
Review
Published 08 Sep 2023

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds

  • Hui Yu and
  • Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

Graphical Abstract
  • products [25][26][27][28][29][30][31]. Ether motifs can significantly modify the pharmacological properties of parent molecules, including increasing lipophilicity and affecting half-life, which play a crucial role in biology, pharmaceuticals, and pesticides [32][33]. Some examples of ether-containing
PDF
Album
Review
Published 06 Sep 2023

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

Graphical Abstract
  • the modification of the chiral auxiliaries as well as of the other fragments of the tridentate ligand have been made to improve stereocontrolling efficiency and to modify physicochemical properties of the template (such as solubility, lipophilicity, etc). Thus, various substituents (4,5-di-CH3 [21], 2
PDF
Album
Supp Info
Full Research Paper
Published 27 Apr 2023

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

  • Ita Hajdin,
  • Romana Pajkert,
  • Mira Keßler,
  • Jianlin Han,
  • Haibo Mei and
  • Gerd-Volker Röschenthaler

Beilstein J. Org. Chem. 2023, 19, 541–549, doi:10.3762/bjoc.19.39

Graphical Abstract
  • . Phosphonates containing CF2 groups can sterically and electronically mimic oxygen, enabling the second dissociation constant, pKa2, to closer mirror those of the phosphates due to the electron-withdrawing effect of fluorine [39]. As a result, improved lipophilicity, metabolic stability or bioavailability of
PDF
Album
Supp Info
Letter
Published 25 Apr 2023

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

Graphical Abstract
  • depicted in this section. I.1) Transition-metal-catalyzed C–H trifluoromethylthiolation of aromatic C(sp2) centers Thanks to its unique features such as an interesting lipophilicity (Hansch parameter = 1.44) [79][80] and a strong withdrawing character, the development of new methodologies for the
PDF
Album
Review
Published 17 Apr 2023

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

  • Nicoleta G. Hădărugă,
  • Gabriela Popescu,
  • Dina Gligor (Pane),
  • Cristina L. Mitroi,
  • Sorin M. Stanciu and
  • Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

Graphical Abstract
  • biologically active molecules on CD-coated polymers used in chromatography [62]. PCA was used for the evaluation of the similarity/dissimilarity of some pesticides, especially fungicides and herbicides, using the effect of a water-soluble β-CD polymer on the apparent pesticide’s lipophilicity [63]. Also
PDF
Album
Supp Info
Full Research Paper
Published 28 Mar 2023

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

Graphical Abstract
  • ]. A survey of the evolution of commercially available chemical libraries is also of real interest [97]. It turns out that a low lipophilicity, a higher fraction of sp3 carbons [98] in the structures as well as a minimum of 20 compounds per scaffold are currently favored. A high sp3 proportion along
PDF
Album
Perspective
Published 29 Sep 2022

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

  • Jamshid Amiri Moghaddam,
  • Huijuan Guo,
  • Karsten Willing,
  • Thomas Wichard and
  • Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

Graphical Abstract
  • prenyltransferase; Introduction Marine bacteria harbor an enormous potential to produce structurally diverse natural products, including prenylated aromatic metabolites [1][2]. Prenylation of metabolites most often confers increased biological activities due to enhanced lipophilicity, solubility, and improved
PDF
Album
Supp Info
Full Research Paper
Published 22 Jun 2022

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

  • Inaiá O. Rocha,
  • Yuri G. Kappenberg,
  • Wilian C. Rosa,
  • Clarissa P. Frizzo,
  • Nilo Zanatta,
  • Marcos A. P. Martins,
  • Isadora Tisoco,
  • Bernardo A. Iglesias and
  • Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

Graphical Abstract
  • electron-withdrawing group that enhances the effects of many bioactive molecules due to a significant improvement in stability, lipophilicity, and resistance to enzymatic degradation [17][18]. Also, it has been widely applied as a special alkyl substituent for ligands of phosphorescent heavy metal
PDF
Album
Supp Info
Full Research Paper
Published 01 Dec 2021

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

  • Dušan Đ. Škorić,
  • Olivera R. Klisurić,
  • Dimitar S. Jakimov,
  • Marija N. Sakač and
  • János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

Graphical Abstract
  • bile acids, derivatives with altered hydrophobicity are being studied [12][13][14]. The tetrazole moiety can be found in many biologically active compounds, and monosubstituted tetrazole is being used in medicinal chemistry as a bioisostere of carboxylic acid [15] because it increases the lipophilicity
PDF
Album
Supp Info
Full Research Paper
Published 20 Oct 2021

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

  • Luiz Claudio Ferreira Pimentel,
  • Lucas Villas Boas Hoelz,
  • Henayle Fernandes Canzian,
  • Frederico Silva Castelo Branco,
  • Andressa Paula de Oliveira,
  • Vinicius Rangel Campos,
  • Floriano Paes Silva Júnior,
  • Rafael Ferreira Dantas,
  • Jackson Antônio Lamounier Camargos Resende,
  • Anna Claudia Cunha,
  • Nubia Boechat and
  • Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

Graphical Abstract
  • a side chain (R), derivatives with aliphatic side chains showed greater toxic activity against K562 cells (Figure 3). One hypothesis is that the derivatives that present higher lipophilicity (2c, 2d, and 2g) quantified by the octanol–water partition coefficient (cLogP, calculated by ALOGPS) as shown
PDF
Album
Supp Info
Full Research Paper
Published 01 Sep 2021

A study on selective transformation of norbornadiene into fluorinated cyclopentane-fused isoxazolines

  • Zsanett Benke,
  • Attila M. Remete and
  • Loránd Kiss

Beilstein J. Org. Chem. 2021, 17, 2051–2066, doi:10.3762/bjoc.17.132

Graphical Abstract
  • enhance the pharmacokinetic properties of lead candidates in drug research through the improvement in lipophilicity, absorption, distribution, hydrophobicity and metabolism. Considering the high importance of organofluorine chemistry and that of fluoroalkyl groups in pharmaceutical chemistry, a wide range
PDF
Album
Supp Info
Full Research Paper
Published 13 Aug 2021

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

  • Vojtěch Hamala,
  • Lucie Červenková Šťastná,
  • Martin Kurfiřt,
  • Petra Cuřínová,
  • Martin Dračínský and
  • Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

Graphical Abstract
  • modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N-acetyl-ᴅ-glucosamine and ᴅ-galactosamine analogs. The key intermediates are the corresponding multiply fluorinated glucosazide and galactosazide
  • molecules [12]. The fluorination of sugars is also a promising strategy to improve unfavorable pharmacokinetic properties of natural carbohydrates such as low lipophilicity [13][14][15][16] and fast metabolic degradation [17][18][19]. Over the last few years, considerable effort has been expended on the
PDF
Album
Supp Info
Full Research Paper
Published 11 May 2021

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

  • Peter Jonas Wickhorst,
  • Mathilda Blachnik,
  • Denisa Lagumdzija and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

Graphical Abstract
  • compared to ct DNA. Since the ligands show essentially the same DNA binding properties as the parent berberine (1a), they have the potential to exhibit a similar DNA-targeted bioactivity. The latter may even be improved due to the higher lipophilicity and thus more balanced bioavailability of the ligands
PDF
Album
Supp Info
Full Research Paper
Published 04 May 2021

Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

  • Carl Recsei and
  • Yaniv Barda

Beilstein J. Org. Chem. 2021, 17, 813–818, doi:10.3762/bjoc.17.70

Graphical Abstract
  • 5 h, with 85% hydrolysis observed after 20 hours. The relative stability of 11 to acidic hydrolysis and its presumably enhanced lipophilicity with respect to a des-fluoro acetal, might presage a role for compounds possessing the acyclic bis(aryloxy)fluoromethane moiety in medicinal or agrochemical
PDF
Album
Supp Info
Letter
Published 12 Apr 2021

DNA with zwitterionic and negatively charged phosphate modifications: Formation of DNA triplexes, duplexes and cell uptake studies

  • Yongdong Su,
  • Maitsetseg Bayarjargal,
  • Tracy K. Hale and
  • Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2021, 17, 749–761, doi:10.3762/bjoc.17.65

Graphical Abstract
  • supports the insignificant difference in the lipophilicity of the diastereomeric ONs. We hypothesised that, in comparison with native ONs, the N+ONs should hybridise with higher affinity to complementary single-stranded DNA (ssDNA) or RNA due to both a reduced repulsion between negatively charged
PDF
Album
Supp Info
Full Research Paper
Published 29 Mar 2021

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

  • Xiaojuan Li,
  • Qiang Zhang,
  • Weigang Zhang,
  • Jinzhu Ma,
  • Yi Wang and
  • Yi Pan

Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49

Graphical Abstract
  • by introducing fluorine-containing (such as -CF3, -CF2H, -C2F5, -SCF3, -OCF3) moieties has become a substantial strategy for medicinal research [2][7][8]. Among the fluorinated functionalities, the trifluoromethylthio group (SCF3) has strong electron-withdrawing properties and a higher lipophilicity
PDF
Album
Supp Info
Full Research Paper
Published 24 Feb 2021

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

  • Vladimir Kubyshkin,
  • Rebecca Davis and
  • Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

Graphical Abstract
  • Lipophilicity The impact of fluorine substitution on the global polarity of the molecule is another parameter that should be considered. The global polarity can be typically analyzed by measurements of the molecular partitioning, e.g., the lipophilicity index logP. For aliphatic organofluorine compounds, this
PDF
Album
Review
Published 15 Feb 2021

The preparation and properties of 1,1-difluorocyclopropane derivatives

  • Kymbat S. Adekenova,
  • Peter B. Wyatt and
  • Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Graphical Abstract
PDF
Album
Review
Published 26 Jan 2021

Decarboxylative trifluoromethylthiolation of pyridylacetates

  • Ryouta Kawanishi,
  • Kosuke Nakada and
  • Kazutaka Shibatomi

Beilstein J. Org. Chem. 2021, 17, 229–233, doi:10.3762/bjoc.17.23

Graphical Abstract
  • ]. Introducing a trifluoromethylthio group (CF3S–), which has high lipophilicity and strong electron-withdrawing properties, into medicinal compounds can improve their pharmacokinetic properties [7][8][9][10][11]. Hence, the development of a synthetic method for the preparation of trifluoromethyl thioethers has
PDF
Album
Supp Info
Full Research Paper
Published 25 Jan 2021
Other Beilstein-Institut Open Science Activities