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  1. Book ; Online: Bioactive Marine Heterocyclic Compounds

    Usami, Yoshihide

    2021  

    Keywords Medicine ; altercrasins ; Alternaria sp ; Anthocidaris crassispina ; decalin derivatives ; cytotoxicity ; mangrove plant ; endophytic fungus ; Cladosporium cladosporioides ; polyketides ; antimicrobial activity ; acetylcholinesterase ; enzymatic inhibitory activity ; genome sequencing ; gene disruption ; lobophorin ; metabolic engineering ; genome mining ; solid-state fermentation ; solid-state extraction ; Chrysosporium lobatum ; marine fungi ; phenalenone derivatives ; antibiotics ; natural product ; P. gingivalis ; methicillin-resistant S. aureus ; azole-based peptide ; marine sponge ; peptide synthesis ; cyanobacteria ; thiazole ; bioactivity ; agesasines ; bromopyrrole alkaloid ; Agelas
    Size 1 electronic resource (132 pages)
    Publisher MDPI - Multidisciplinary Digital Publishing Institute
    Publishing place Basel, Switzerland
    Document type Book ; Online
    Note English ; Open Access
    HBZ-ID HT021291590
    ISBN 9783036527536 ; 3036527532
    Database ZB MED Catalogue: Medicine, Health, Nutrition, Environment, Agriculture

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  2. Article: Generation of Alkylidene Carbenes through Tetrazole Fragmentation: Recent Advances and Applications in Organic Synthesis

    Harusawa, Shinya / Yoneyama, Hiroki / Usami, Yoshihide

    Synthesis

    2024  

    Abstract: Tetrazole fragmentation under mild conditions from 5-hydroxyalkyl-1 H -tetrazoles (HATs) or cyanophosphates (CPs) readily generates the corresponding alkylidene carbenes, which undergo [1,2]-rearrangements or [1,5]-C–H insertions to yield one-carbon ... ...

    Abstract Tetrazole fragmentation under mild conditions from 5-hydroxyalkyl-1 H -tetrazoles (HATs) or cyanophosphates (CPs) readily generates the corresponding alkylidene carbenes, which undergo [1,2]-rearrangements or [1,5]-C–H insertions to yield one-carbon homologous alkynes or five-membered unsaturated carbocycles, respectively. Furthermore, azido-HATs and 2-cyanoazetidines afford propargylic and homopropargylic amines, respectively, via [1,2]-rearrangement of the corresponding aminoalkyl alkylidene carbenes. These reactions are successfully applied for the synthesis of various biofunctional molecules. This short review summarizes the progress made on this methodology over the last decade. 1

    Introduction 2

    Early Studies 3

    Tetrazole Fragmentation of HATs, Azido-HATs, and 2-Cyanoazetidines 4

    HAT Synthetic Methods 5

    Tetrazole Fragmentation from CPs 6

    Summary and Perspective
    Keywords alkylidene carbene ; tetrazole ; fragmentation ; 5-hydroxyalkyl-1 ; -tetrazole ; α-hydroxy-β-azidoalkyl-1 ; -tetrazoles ; 2-cyanoazetidine ; cyanophosphate
    Language English
    Publishing date 2024-02-02
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/a-2260-5652
    Database Thieme publisher's database

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  3. Article ; Online: Identification of novel metabolites of abiraterone in human serum and their metabolic pathways.

    Horiyama, Shizuyo / Hayama, Noboru / Yoneyama, Hiroki / Usami, Yoshihide / Haginaka, Jun

    Analytical sciences : the international journal of the Japan Society for Analytical Chemistry

    2023  Volume 40, Issue 1, Page(s) 67–74

    Abstract: Two novel abiraterone (Abi, 3β-OH-Abi) metabolites in human serum were identified as 3α-OH-Abi and ... ...

    Abstract Two novel abiraterone (Abi, 3β-OH-Abi) metabolites in human serum were identified as 3α-OH-Abi and Δ
    MeSH term(s) Humans ; Chromatography, Liquid ; Tandem Mass Spectrometry ; Hydroxysteroid Dehydrogenases ; Metabolic Networks and Pathways
    Chemical Substances abiraterone (G819A456D0) ; Hydroxysteroid Dehydrogenases (EC 1.1.-)
    Language English
    Publishing date 2023-10-13
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1483376-1
    ISSN 1348-2246 ; 1348-2246
    ISSN (online) 1348-2246
    ISSN 1348-2246
    DOI 10.1007/s44211-023-00431-4
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Transformation of Benzaldehydes to Benzonitriles via Cyanophosphates without One-Carbon Homologation

    Yoneyama, Hiroki / Okada, Ayami / Hayama, Noboru / Harusawa, Shinya / Usami, Yoshihide

    Synthesis

    2024  

    Abstract: The transformation of benzaldehydes into benzonitriles via cyanophosphates (CPs) with tetrabutylammonium azide (Bu 4 N·N 3 ) was found to afford a range of benzonitriles in modest-to-high yields. As the CN-carbon of benzonitriles arises from the formyl- ... ...

    Abstract The transformation of benzaldehydes into benzonitriles via cyanophosphates (CPs) with tetrabutylammonium azide (Bu 4 N·N 3 ) was found to afford a range of benzonitriles in modest-to-high yields. As the CN-carbon of benzonitriles arises from the formyl-carbon of benzaldehydes, this is a new type of CP-reaction, distinctly different from the past one-carbon nitrile homologation. In contrast, the reaction of ketone- or aliphatic aldehyde-CPs with Bu 4 N·N 3 resulted in mono-deethylaton forming tetrabutylammonium salts.
    Keywords cyanophosphate ; tetrabutylammonium azide ; mono-deethylaton ; benzonitrile ; tetrabutylammonium salt
    Language English
    Publishing date 2024-03-07
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/a-2283-6798
    Database Thieme publisher's database

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  5. Article ; Online: C4-Alkylamination of C4-Halo-1

    Usami, Yoshihide / Tatsui, Yuya / Yoneyama, Hiroki / Harusawa, Shinya

    Molecules (Basel, Switzerland)

    2020  Volume 25, Issue 20

    Abstract: Alkylamino coupling reactions at the C4 positions of 4-halo- ... ...

    Abstract Alkylamino coupling reactions at the C4 positions of 4-halo-1
    MeSH term(s) Catalysis ; Copper/chemistry ; Palladium/chemistry ; Pyrazoles/chemistry
    Chemical Substances Pyrazoles ; Palladium (5TWQ1V240M) ; Copper (789U1901C5)
    Language English
    Publishing date 2020-10-12
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules25204634
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.MO 81: Show issues

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  6. Article ; Online: C4-Alkylamination of C4-Halo-1 H -1-tritylpyrazoles Using Pd(dba) 2 or CuI

    Yoshihide Usami / Yuya Tatsui / Hiroki Yoneyama / Shinya Harusawa

    Molecules, Vol 25, Iss 4634, p

    2020  Volume 4634

    Abstract: Alkylamino coupling reactions at the C4 positions of 4-halo-1 H -1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba) 2 catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly ...

    Abstract Alkylamino coupling reactions at the C4 positions of 4-halo-1 H -1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba) 2 catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly using t BuDavePhos as a ligand. As a substrate, 4-Bromo-1-tritylpyrazole was more effective than 4-iodo or chloro-1-tritylpyrazoles. Meanwhile, the CuI mediated C-N coupling reactions of 4-iodo-1 H -1-tritylpyrazole were effective for alkylamines possessing a β-hydrogen atom.
    Keywords amination ; 4-halopyrazole ; Buchwald-Hartwig coupling ; Pd(dba) 2 ; CuI mediated coupling ; aliphatic amine ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2020-10-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  7. Article ; Online: Enantiomeric composition of natural pericosine A derived from Periconia byssoides and α-glycosidase inhibitory activity of (-)-enantiomer.

    Usami, Yoshihide / Nakamura, Kimika / Mizobuchi, Yoshino / Mizuki, Koji / Harusawa, Shinya / Yoneyama, Hiroki / Yamada, Takeshi

    Chirality

    2022  Volume 34, Issue 10, Page(s) 1320–1327

    Abstract: Chiral high-performance liquid chromatography (HPLC) analysis of natural pericosine A, which appeared in literature first in 1977, from Periconia byssoides was conducted using a column CHIRALPAK® AD-H to determine the enantiomeric composition of the ... ...

    Abstract Chiral high-performance liquid chromatography (HPLC) analysis of natural pericosine A, which appeared in literature first in 1977, from Periconia byssoides was conducted using a column CHIRALPAK® AD-H to determine the enantiomeric composition of the original mixture which was found to be 68: 32 mixtures of (+)- and (-)-enantiomer, respectively. Furthermore, two independently isolated samples of pericosine A from the same fungus were also analyzed to show the two peaks in the HPLC charts at approximate 1:1 ratio. These results concluded that pericosine A derived from Periconia byssoides was indeed an enantiomeric mixture. Synthesized enantiomers were subjected to evaluation of antitumor activity against three kinds of tumor cells (p388, L1210, HL-60), indicating moderate cytotoxicity against all three kinds of tumor cell lines, but significant difference in potency between the enantiomers was not observed. In contrast, when both the enantiomers of pericosine A were evaluated against five kinds of glycosidases-inhibitory activities (α- and β-glucosidases, α- and β-galactosidases, and α-mannosidase), an apparent difference on anti-glycosidase assay was found between the enantiomers: (-)-pericosine A inhibited α-glucosidase at IC
    MeSH term(s) Ascomycota/chemistry ; Chromatography, High Pressure Liquid/methods ; Shikimic Acid/analogs & derivatives ; Shikimic Acid/chemistry ; Stereoisomerism
    Chemical Substances methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate ; Shikimic Acid (29MS2WI2NU)
    Language English
    Publishing date 2022-07-01
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1011639-4
    ISSN 1520-636X ; 0899-0042
    ISSN (online) 1520-636X
    ISSN 0899-0042
    DOI 10.1002/chir.23491
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2594: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  8. Article: Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities

    Usami, Yoshihide / Mizobuchi, Yoshino / Ijuin, Mai / Yamada, Takeshi / Morita, Mizuki / Mizuki, Koji / Yoneyama, Hiroki / Harusawa, Shinya

    Marine drugs. 2022 June 30, v. 20, no. 7

    2022  

    Abstract: The enantiomers of 6-fluoro-, 6-bromo-, and 6-iodopericosine A were synthesized. An efficient synthesis of both enantiomers of pericoxide via 6-bromopericosine A was also developed. These 6-halo-substituted pericosine A derivatives were evaluated in ... ...

    Abstract The enantiomers of 6-fluoro-, 6-bromo-, and 6-iodopericosine A were synthesized. An efficient synthesis of both enantiomers of pericoxide via 6-bromopericosine A was also developed. These 6-halo-substituted pericosine A derivatives were evaluated in terms of their antitumor activity against three types of tumor cells (p388, L1210, and HL-60) and glycosidase inhibitory activity. The bromo- and iodo-congeners exhibited moderate antitumor activity similar to pericosine A against the three types of tumor cell lines studied. The fluorinated compound was less active than the others, including pericosine A. In the antitumor assay, no significant difference in potency between the enantiomers was observed for any of the halogenated compounds. Meanwhile, the (−)-6-fluoro- and (−)-6-bromo-congeners inhibited α-glucosidase to a greater extent than those of their corresponding (+)-enantiomers, whereas (+)-iodopericosine A showed increased activity when compared to its (−)-enantiomer.
    Keywords antineoplastic activity ; enantiomers ; neoplasm cells ; neoplasms
    Language English
    Dates of publication 2022-0630
    Publishing place Multidisciplinary Digital Publishing Institute
    Document type Article
    ZDB-ID 2175190-0
    ISSN 1660-3397
    ISSN 1660-3397
    DOI 10.3390/md20070438
    Database NAL-Catalogue (AGRICOLA)

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  9. Article: A novel synthetic method of 2,4-disubstituted oxazoles using carboxylic acid-derived Bu2Sn[OC(O)R]2

    Yoneyama, Hiroki / Oka, Naoki / Usami, Yoshihide / Harusawa, Shinya

    Tetrahedron letters. 2020 June 11, v. 61, no. 24

    2020  

    Abstract: A novel synthetic method for the preparation of 2,4-disubstituted oxazoles was developed, entailing the reaction of dibutyltin diacylates Bu2Sn[OC(O)R]2 with 1-substituted acetylenes and TMSN3 to afford a range of 2,4-disubstituted oxazoles in good ... ...

    Abstract A novel synthetic method for the preparation of 2,4-disubstituted oxazoles was developed, entailing the reaction of dibutyltin diacylates Bu2Sn[OC(O)R]2 with 1-substituted acetylenes and TMSN3 to afford a range of 2,4-disubstituted oxazoles in good yields.
    Keywords alkynes ; chemical reactions ; chemical structure ; dibutyltin ; oxazoles
    Language English
    Dates of publication 2020-0611
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2020.151983
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2837: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
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    Jg. 1995 - 2021: Lesesall (2.OG)
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  10. Article: TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis

    Yoneyama, Hiroki / Oka, Naoki / Usami, Yoshihide / Harusawa, Shinya

    Tetrahedron letters. 2020 Feb. 20, v. 61, no. 8

    2020  

    Abstract: Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 °C in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger ... ...

    Abstract Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 °C in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.
    Keywords benzene ; chemical reactions ; chemical structure ; nitriles ; temperature ; toluene
    Language English
    Dates of publication 2020-0220
    Publishing place Elsevier Ltd
    Document type Article
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2019.151517
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2837: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
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