Biologically Active Organofluorine Compounds

Hiyama, Tetsuo; Yamamoto, Hisashi

doi:10.1007/978-3-662-04164-2_5

Cited by 115 publications

(79 citation statements)

References 93 publications

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“…125.4,125.9,126.9,128.0,129.2,129.3,129.9,131.5,m),ddt,J = 297.3,53.7,7.2 Hz). 2,3,3,4,4,5, = 52.1,5.5 Hz),m),m). 13 C NMR  13.8,22.4,28.2,29.0,31.2,33.4,44.2 (t,m),121.7,125.3,125.8,127.0,128.0,129.2,129.3,129.7,131.1,133.7.…”

Section: -(222-trifluoro-1-(hexylsulfanyl)ethyl)benzo[b]thiophene mentioning

confidence: 99%

“…Oil 2, 14.0,22.4,28.3,29.0,31.3,33.1,43.3 (q,55.7,56.3,111.9,114.8,114.9,123.4,126.3 2,2,3,4,5,6,7, Oil: IR ( …”

Section: -{222-trifluoro-1-(phenlsulfanyl)ethyl}naphthalene (2b)mentioning

confidence: 99%

“…13 C NMR  13.8,22.4,28.2,29.0,31.2,33.4,44.2 (t,m),121.7,125.3,125.8,127.0,128.0,129.2,129.3,129.7,131.1,133.7. 19 1,2,2,3, 1- (1,1,2,2,3,3,4,4,5, 5- (2,2,uracil (6) 5-(2,2,2-Trifluoro-1-hydroxyethyl)uracil 6 was prepared by the modification of the reported procedure [13]. A mixture of uracil (3.37 g, 30 mmol) and trifluoroacetaldehyde ethyl hemiacetal (containing 10% EtOH) in DMF (18 mL) was stirred at 120 C for 15 h. After cooling to room temperature, the mixture was poured into saturated aqueous NH 4 Cl (30 mL) and extracted with AcOEt (20 mL X 3).…”

Section: -(222-trifluoro-1-(hexylsulfanyl)ethyl)benzo[b]thiophene mentioning

confidence: 99%

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A novel method for introducing a polyfluoroalkyl group into aromatic compounds

Tahara

Fukuhara

Hara

2011

Journal of Fluorine Chemistry

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Introduction of a polyfluoroalkyl group into aromatic compounds was achieved by Friedel-Crafts reaction using (1-chloro-1-hydroperfluoroalkyl) sulfides 1, and the subsequent desulfurizing-difluorination of the resulting product using IF 5 / Et 3 N-nHF.Perfluoroethyl, 1,1,2,2,3,3-hexafluoropropyl, and 1,1,2,2,3,3,4,4,5,5-decafluoropentyl groups were introduced to various aromatic compounds by this method. Selective perfluoroethylation of uracil at the 5-position was also performed.

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Section: -(222-trifluoro-1-(hexylsulfanyl)ethyl)benzo[b]thiophene mentioning

confidence: 99%

“…Oil 2, 14.0,22.4,28.3,29.0,31.3,33.1,43.3 (q,55.7,56.3,111.9,114.8,114.9,123.4,126.3 2,2,3,4,5,6,7, Oil: IR ( …”

Section: -{222-trifluoro-1-(phenlsulfanyl)ethyl}naphthalene (2b)mentioning

confidence: 99%

Section: -(222-trifluoro-1-(hexylsulfanyl)ethyl)benzo[b]thiophene mentioning

confidence: 99%

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A novel method for introducing a polyfluoroalkyl group into aromatic compounds

Tahara

Fukuhara

Hara

2011

Journal of Fluorine Chemistry

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“…Briefly, 100 µl of the test bacteria/ fungi were grown in 10 ml of fresh media until they reached a count of approximately 10 8 cells/ml for bacteria or 10 5 cells/ml for fungi [15]. 100 µl of microbial suspension was spread onto agar plates corresponding to the broth in which they were maintained.…”

Section: Biologymentioning

confidence: 99%

Green Synthesis of Novel 5-Arylazo-2- [(2S, 3S, 4R, 5R)-3, 4, 5- trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile.

Mmh¹,

Ah²,

M³

et al. 2017

Chem Sci J

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Green Synthesis of Novel 5-Arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile IntroductionPyridine nucleus is one of the most interesting nucleus in organic synthesis. Many uses of pyridines derivatives were investigated in the recent decades especially fluorinated derivatives. One of the recent researches discovered that high tuberculostearic activity of pyridine was observed [1,2].Also from the amazing character of some pyridine is its high fluorescence activities which was used as molecular sensor of picric acid [3].It has been of great importance in the exploring of some novel antimicrobial compounds in veterinary as well as human medicine worldwide. Genetic mutation and acquisition of mobile drug resistance genes of microorganisms is a very great resistance and barrier in treating animal and human patients with infectious diseases [4,5]. The importance of the synthesis of novel derivatives of pyridine nucleosides due to their potential use to treat various diseases, such as hepatitis cancer and microbial infections [6][7][8][9][10].Fluorinated derivatives of pyridines are of high significance in pharmaceutical and medicinal chemistry [11]. Synthesis of poly substituted fluroarylazopyridone by using green protocol is of great effect in synthetic chemistry and also in pharmaceutical chemistry [12]. The presence of fluorine atoms in the molecule can change its lipophilicity, which also affect and change the rate of transportation through lipid membranes [13]. Achievement of green and sustainable chemistry protocol instead of classical methods synthetic chemistry nowadays is of high interest, especially in synthesis of some novel Fluro arylazo pyridine derivatives (1a-e) and their nucleosides (3a-e). Methodology ChemistryGeneral coupling procedures of synthesis of Acetylated -arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4,6dimethylnicotinonitrile AbstractPyridine derivatives played important roles in the last decade in to approach many and different functionalities, especially as antitumor, antibacterial, anti-fungal, and many of pharmacological activities. Novel compounds of 5-Arylazo-2-[(substituted)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4,6dimethyl nicotine nitrile, (3a-e), generally called (Fluro arylazo pyridine glucosides) were synthesised via green protocol, microwave scheme 3, and the compounds were investigated on the basis of spectroscopic data (FT-IR, 1D, 13 C), and antibacterial and antifungal studies had been applied. Microwave method: A mixture of 2(1H)-pyridines (1a-e) (10 mmol) and 1″,2″,3″,4″,6″-penta-O-acetyl-α-D-glucopyranose (11 mmol, 4.29 g) where be dissolved in a mixture of methylene chloride/methanol (80/20) then silica gel (200-400 mesh) where be added after that the excess solvent was removed by evaporation. The dried residue was transferred into a 10 mL vial and subjected to microwave irradiation for 2-3 minutes using CEM Microwave syst...

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“…The presence of additional functional groups in the aliphatic chain modifies both the physical properties and therapeutic effect of SFAE, thus enhancing its biological effectiveness and spectrum [19][20][21][22]. These include phenyl, hydroxyl, amino, hydroxyphenyl, methoxy-phenyl and halogen-containing moieties, e.g., phenyl-fluorine, or alkyl halides [23][24][25][26]. Out of the mentioned modifiers, the fluorine most profoundly alters the molecule's biological functions (i.e., increases the free-radical production; influences bio-retention due to increased hydrophobicity of a given molecule) [27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Influence of Chemical Modifications of Polyhydroxyalkanoate-Derived Fatty Acids on Their Antimicrobial Properties

et al. 2019

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Sugar esters are bioactive compounds derived from renewable resources. They consist of a sugar moiety with attached non-polar part – usually a fatty acid. These compounds find uses in cosmetic, food and pharmaceutical industries as surfactants due to their physicochemical and antimicrobial activities. In this study we have produced fatty acids for sugar ester synthesis from bacterially derived polyesters, namely polyhydroxyalkanoates (PHAs). We have developed methodology to decorate PHA monomers with a fluorinated moiety. With aid of biocatalysis a series of glucose esters was created with unmodified and modified PHA monomers. All synthesised compounds showed moderate antimicrobial activity.

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Biologically Active Organofluorine Compounds

Cited by 115 publications

References 93 publications

A novel method for introducing a polyfluoroalkyl group into aromatic compounds

A novel method for introducing a polyfluoroalkyl group into aromatic compounds

Green Synthesis of Novel 5-Arylazo-2- [(2S, 3S, 4R, 5R)-3, 4, 5- trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile.

Influence of Chemical Modifications of Polyhydroxyalkanoate-Derived Fatty Acids on Their Antimicrobial Properties

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