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Search for "lipophilicity" in Full Text gives 138 result(s) in Beilstein Journal of Organic Chemistry.

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

  • Alyn T. Davies,
  • Mark D. Greenhalgh,
  • Alexandra M. Z. Slawin and
  • Andrew D. Smith

Beilstein J. Org. Chem. 2020, 16, 1572–1578, doi:10.3762/bjoc.16.129

Graphical Abstract
  • ]. The incorporation of this motif is widely employed within the pharmaceutical, agrochemical, and materials industries as it can be used strategically to increase lipophilicity as well as to enhance metabolic stability and binding selectivity [7][8][9]. In this context, the generation of effective and
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Published 30 Jun 2020

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

  • Alexander V. Nyuchev,
  • Ting Wan,
  • Borja Cendón,
  • Carlo Sambiagio,
  • Job J. C. Struijs,
  • Michelle Ho,
  • Moisés Gulías,
  • Ying Wang and
  • Timothy Noël

Beilstein J. Org. Chem. 2020, 16, 1305–1312, doi:10.3762/bjoc.16.111

Graphical Abstract
  • properties, for example, a high electronegativity (χ = 3.7), and a high lipophilicity (Hansch-Leo parameter π = 1.04, intermediate between the -CF3 and the -SCF3 values, respectively, 0.88 and 1.44) [4]. From a pharmaceutical perspective, the former property provides stability of the drug under physiological
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Published 15 Jun 2020

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

  • Abimelek Cortes-Pacheco,
  • María Adelina Jiménez-Arellanes,
  • Francisco José Palacios-Can,
  • José Antonio Valcarcel-Gamiño,
  • Rodrigo Said Razo-Hernández,
  • María del Carmen Juárez-Vázquez,
  • Adolfo López-Torres and
  • Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

Graphical Abstract
  • could be the difference in lipophilicity between the aliphatic esters 3 and 4, which were less lipophilic (by means of the clogP value of 0.58 and 1.39, respectively) compared to the aromatic derivatives 5 and 6 (clogP = 1.80 and 1.85, respectively), with the last being the most permeable one through
  • compounds was opposed to that observed with the TPA topical model. This may be a consequence of the lower lipophilicity of 3 (clogP = 0.58) and 4 (clogP = 1.39) compared to 5 (clogP = 1.80) and 6 (clogP = 1.85), influencing the better dissolution of 3 and 4 in an aqueous medium prior to its absorption
  • active one, followed by 5, 3, and 4 in that order (Table 1). Thus, the efficacy of the tested compounds 3–6 was well correlated with the lipophilicity and the predicted interaction energy with MMP-8 (Table 4). Next, we searched for other energy interaction features from the docking calculation. As
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Published 08 Jun 2020

Anthelmintic drug discovery: target identification, screening methods and the role of open science

  • Frederick A. Partridge,
  • Ruth Forman,
  • Carole J. R. Bataille,
  • Graham M. Wynne,
  • Marina Nick,
  • Angela J. Russell,
  • Kathryn J. Else and
  • David B. Sattelle

Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105

Graphical Abstract
  • structure–activity relationships for tolfenpyrad (19) [169]. The main objective of this work was to reduce the lipophilicity of tolfenpyrad 19, which was considered undesirable for an orally administered agent, as typical of anthelmintics, compared to a surface-applied pesticide. This was accomplished
  • lipophilicity. Conversely, modifications to the pyrazole group gave rise to more dramatic changes in the potency. For instance, while changing the ethyl substituent within 20 to a methyl substituent in 22 gave a slight increase in potency, removal of the ethyl group in 23 showed a substantial improvement in the
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Published 02 Jun 2020

Fluorinated phenylalanines: synthesis and pharmaceutical applications

  • Laila F. Awad and
  • Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

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  • the properties of peptides and proteins [5][6][7], influencing aspects such as protein folding, protein–protein interactions, ribosomal translation, lipophilicity, acidity/basicity, optimal pH, stability, thermal stability, and therapeutic properties [8][9][10]. This extends to metabolic properties of
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Published 15 May 2020

Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

  • Balaram S. Takale,
  • Ruchita R. Thakore,
  • Elham Etemadi-Davan and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

Graphical Abstract
  • functional groups into existing or new drugs. Examples include the incorporation of silicon bioisosteres that help increase lipophilicity, subsequently altering the existing metabolic pathway of a drug due to differences in its physicochemical properties [8]. On the other hand, the trigonal planar nature of
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Published 15 Apr 2020

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

  • Ming-Xi Bi,
  • Shuai Liu,
  • Yangen Huang,
  • Xiu-Hua Xu and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

Graphical Abstract
  • involved in these transformations. Keywords: cyclization; indole derivatives; oxidation; radical reaction; trifluoromethylthiolation; Introduction The trifluoromethylthio (SCF3) group could significantly improve the lipophilicity of organic molecules as shown by its high Hansch constant (π = 1.44 for
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Published 08 Apr 2020

Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

  • Clément Ghiazza and
  • Anis Tlili

Beilstein J. Org. Chem. 2020, 16, 305–316, doi:10.3762/bjoc.16.30

Graphical Abstract
  • they confer very high lipophilicity [1][2]. In this context, transition-metal catalysis plays a key role in the formation of carbon–chalcogen trifluoromethyl bonds. Major advances have been made in the last ten years especially for C–OCF3 [3][4][5] and C–SCF3 [6][7][8] bond-forming processes. Today
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Published 03 Mar 2020

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

  • Valentina A. Ol’shevskaya,
  • Elena G. Kononova and
  • Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

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  • on 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (1) as the starting compound. The presence of fluorine atoms on the four phenyl rings at the meso-positions of the porphyrin structure can make a strong influence on the hydrophobic interactions and lipophilicity, metabolic stability, thus modulating
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Published 13 Nov 2019

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

  • Pedro H. P. R. Carvalho,
  • Jose R. Correa,
  • Karen L. R. Paiva,
  • Daniel F. S. Machado,
  • Jackson D. Scholten and
  • Brenno A. D. Neto

Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257

Graphical Abstract
  • agreed well with the experimental data obtained for the newly developed dye. DFT calculations were also employed to forecast the lipophilic character of the dye utilizing several XCFs. Experimentally, lipophilicity can be measured by means of the logarithm of the n-octanol/water partition coefficient
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Published 06 Nov 2019

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

  • Jessica Matthias,
  • Thines Kanagasundaram,
  • Klaus Kopka and
  • Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

Graphical Abstract
  • . Lipophilic cations such as the phosphonium cation or rhodamines are known to accumulate selectively within the mitochondria, driven by the mitochondrial plasma membrane potential [39][40]. Thereby, the high lipophilicity facilitates the diffusion through the lipid bilayers of the cell and mitochondrial
  • membranes. Recently, a silicon rhodamine for selective mitochondrial staining was developed by conjugation of the SiR core with ten different amines varying in lipophilicity [46]. The authors showed that the optimal range of clogP values for mitochondrial targeting ranges from 5.50 to 6.33. As mentioned
  • application of SiR 15 as a specific NIR mito tracker probe. Pearson coefficients for selective mitochondria staining >0.8 correlate with much higher lipophilicity (clogP over 4.95). Especially SiR-Mito 8 offers a comparable quantum yield to dye 15 (ε and therefore brightness not available) combined with a
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Published 01 Oct 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

Graphical Abstract
  • similar to that of hydrogen atoms. Due to these unique properties, the introduction of fluorine into a molecule can cause dramatic changes, such as the acidity or basicity of neighboring groups, dipole moment, and properties such as lipophilicity, metabolic stability, and bioavailability [1]. Consequently
  • their metabolic stability, lipophilicity, and the ability to penetrate the blood–brain barrier. Similar to fluorination, trifluoromethylation can also be achieved by three reaction types: nucleophilic, electrophilic and radical trifluoromethylation. In recent years, many novel trifluoromethylation
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Published 23 Sep 2019

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

Graphical Abstract
  • and increase of lipophilicity are important approaches in the preparation of muramyl dipeptide analogues with improved pharmacological properties. Mannose receptors present on immunocompetent cells are pattern-recognition receptors and by mannose ligands binding they affect the immune system. Here we
  • with derivatives lacking the adamantane moiety. Immunostimulating properties of synthesized derivatives were assessed in vivo using ovalbumin as an antigen. Results and Discussion Design Desmuramyl peptides enter into the cell by passive absorption and this process depends on lipophilicity [25
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Published 29 Jul 2019

Synthesis of 9-O-arylated berberines via copper-catalyzed CAr–O coupling reactions

  • Qiaoqiao Teng,
  • Xinhui Zhu,
  • Qianqian Guo,
  • Weihua Jiang,
  • Jiang Liu and
  • Qi Meng

Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161

Graphical Abstract
  • agent in clinic. However, a high dosage is often required due to its low lipophilicity and bioavailability. The current study explores the structural modifications of berberines with potentially lipophilic aryl groups to address this problem. A series of 15 9-O-aryl-substituted berberines (3a–o) and one
  • 9-O-phenylene-bridged berberine dimer (5) was synthesized by copper-catalyzed cross-coupling of tetrahydroberberrubine and aryl iodides, followed by oxidation with I2. Keywords: arylation; berberines; cross-coupling; copper; lipophilicity; structural modification; Introduction Berberine (BBR) is a
  • considerable improvements in terms of biological activity (Scheme 1, BBR structure). Among all lipophilicity-enhancing strategies, C9-O-Me substitution is the most intensively studied one, which is primarily due to its synthetic convenience. The synthesis starts with pyrolysis of BBR under vacuum at high
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Published 15 Jul 2019

Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif

  • Andrea Rodil,
  • Alexandra M. Z. Slawin,
  • Nawaf Al-Maharik,
  • Ren Tomita and
  • David O’Hagan

Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144

Graphical Abstract
  • literature [3], substituents which are typically introduced to stop metabolism of aryl rings [4]. Other fluorinated motifs are gaining in importance too, such as aryl–OCF3 and aryl–SCF3 ethers, although these substituents can significantly raise lipophilicity (log P) [5][6]. There are relatively few
  • ) that is marketed as the active component [11][12]. The increase in lipophilicity associated with these substituents is not always desirable. In this regard, partially fluorinated alkyl substituents become an interesting alternative, as the fluorines polarise the adjacent hydrogens and lipophilicity
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Published 28 Jun 2019

Tuning the stability of alkoxyisopropyl protection groups

  • Zehong Liang,
  • Henna Koivikko,
  • Mikko Oivanen and
  • Petri Heinonen

Beilstein J. Org. Chem. 2019, 15, 746–751, doi:10.3762/bjoc.15.70

Graphical Abstract
  • of these acetone-based acetal groups are faster removed than a dimethoxytrityl group, and they are easier to cleave completely in solution. The structural variation allows steering of the stability and lipophilicity of the compounds in some range. Keywords: acetal; hydrolysis; protecting groups
  • [7]. We realized that the lability of the acetal group can be easily steered by varying the alkoxy group, while preserving other beneficial properties of the protecting groups. On the other hand, structural modifications can also affect the lipophilicity of the protected compounds. The present study
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Published 21 Mar 2019

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

  • Hilke Bruns,
  • Lisa Ziesche,
  • Nargis Khakin Taniwal,
  • Laura Wolter,
  • Thorsten Brinkhoff,
  • Jennifer Herrmann,
  • Rolf Müller and
  • Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

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  • and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a
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Published 03 Dec 2018

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

  • Jiang Liu,
  • Peter Leonard,
  • Sebastian L. Müller,
  • Constantin Daniliuc and
  • Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

Graphical Abstract
  • display increased lipophilicity they have the potential to be utilized for the transmembrane delivery of nucleotides and oligonucleotides. More important, all of the macrocyle moieties and the size of the macrocycle can be altered. The system can be regarded as a new lead for further structural and
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Published 13 Sep 2018

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

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  • packaging density of aggregates and their general lipophilicity. To reveal this, absorbance spectra of the 10b–EY system in the presence of ADP and ATP were recorded (Figure 5a and b). The addition of small amounts of nucleotides leads to a bathochromic shift of the EY adsorption due to a deeper penetration
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Published 31 Jul 2018

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

  • Jiyun Sun,
  • Xiaohua Zhen,
  • Huaibin Ge,
  • Guangtao Zhang,
  • Xuechan An and
  • Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

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  • sciences. The introduction of this functional group in drug molecules can enhance their chemical and metabolic stability, improve their lipophilicity and bioavailability, and increase protein-binding affinity [1][2][3][4][5][6]. In this regard, the CF3 group has been introduced into many pharmaceutical
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Published 15 Jun 2018

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

  • Dandan Li,
  • Naoya Oku,
  • Atsumi Hasada,
  • Masafumi Shimizu and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

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  • and 8. Among 1–6, the 2-heptenyl-3-methyl congener 4 was the most active. Compounds 3–6 also inhibited the growth of the fungi R. oryzae and T. rubrum, while 1 and 2 did not. This may to some extent attributable to the global lipophilicity of molecules, as 1and 2 are among the fastest eluting
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Published 14 Jun 2018

An overview of recent advances in duplex DNA recognition by small molecules

  • Sayantan Bhaduri,
  • Nihar Ranjan and
  • Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

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  • lipophilicity [53]. These structural analogs comprise of branched N-alkyl- and N-cycloalkylpyrroles to test the conformational flexibility towards DNA binding. Hydrophobic N-terminal amides and substituted thiazole replacing pyrrole were installed in order to impart more lipophilicity. All these compounds were
  • alkylation. In addition, longer linker imparts more lipophilicity, which in turn, favors better transportation of these compounds into the cells. Anthony et al. reported a series of short MGBs based on the lead compounds distamycin and thiazotropsins with the installation of hydrophobic aromatic head groups
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Published 16 May 2018

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

  • Françoise Debart,
  • Christelle Dupouy and
  • Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

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  • ) [22]. The fundamental advantage of using enzyme-cleavable modifications of the phosphodiester backbone in ONs is to transitorily mask the negative charges of the phosphate by neutral phosphotriesters. Consequently, the backbone is less prone to nuclease degradation, and the lipophilicity of the pro-ON
  • phosphotriester ONs is rather poor [29], the design of ONs combining phosphodiester and phosphotriester linkages is required to ensure aqueous solubility and sufficient lipophilicity for cell uptake. Several attempts to obtain such chimeras were made in Imbach’s laboratory in the early 2000s. In particular, the
  • targeting the nuclease resistance of the ON prodrug. On the other hand, the thermosensitive groups are more suitable for the protection of the thiophosphates flanking the CpG motif of DNA prodrugs to provide both lipophilicity (better cellular uptake) and hydrophilicity (better solubility once groups are
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Published 19 Feb 2018

Progress in copper-catalyzed trifluoromethylation

  • Guan-bao Li,
  • Chao Zhang,
  • Chun Song and
  • Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

Graphical Abstract
  • such as metabolic stability, lipophilicity and permeability [1][2][3][4]. Therefore, organic molecules bearing trifluoromethyl groups are widely used in pharmaceuticals and agrochemicals, such as the antidepressant fluoxetine, the anti-ulcer drug lansoprazole and so on (Figure 1). The specific roles of
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Published 17 Jan 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na

  • Hélène Guyon,
  • Hélène Chachignon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

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  • , judicious installation of CF3 group(s) in catalysts or ligands is an effective tool to tune their reactivity and selectivity in synthesis. As a pharmacophore, CF3 substantially improves the catabolic stability, lipophilicity, and transport rate. In association with chalcogens (OCF3, SCF3, SeCF3), the CF3
  • group imparts enhanced lipophilicity of aromatic compounds in comparison with aryl–CF3 analogues (Hansch’s hydrophobic parameter π(SCF3) = 1.44; π(OCF3) = 1.04 versus π(CF3) = 0.88). Trifluoromethyl sources are manifold displaying nucleophilic, electrophilic or radical reactivities [11]. The most
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Published 19 Dec 2017
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