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  1. Article: Synthesis of new fused dipyrroloazepinones via a two-step tandem reaction: Comparison of the Schmidt and Beckmann pathways

    Xavier Domínguez-Villa, Francisco / Armenta-Salinas, Concepción / Ávila-Zárraga, Gustavo

    Tetrahedron letters. 2020 Apr. 09, v. 61, no. 15

    2020  

    Abstract: A new set of polyheterocyclic compounds (4,7,7-trimethyl-5-aryl-7a,8,9,10-tetrahydrodipyrrolo[3,2-c;2′,1′-g]azepin-2-ones) was synthesized via a tandem process involving a Beckmann rearrangement followed by a cyclization between the nitrogen atom and ... ...

    Abstract A new set of polyheterocyclic compounds (4,7,7-trimethyl-5-aryl-7a,8,9,10-tetrahydrodipyrrolo[3,2-c;2′,1′-g]azepin-2-ones) was synthesized via a tandem process involving a Beckmann rearrangement followed by a cyclization between the nitrogen atom and primary halide fragment. Ring expansion from 6 to 7 members and the fusion of the resulting ring with a five-membered ring took place in just one process.
    Keywords chemical reactions ; chemical structure ; nitrogen ; organic compounds
    Language English
    Dates of publication 2020-0409
    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.2020.151751
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2837: Show issues Location:
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  2. Article ; Online: Novel Sesquiterpene Skeletons by Multiple Wagner-Meerwein Rearrangements of a Longipinane-1,9-diol Derivative.

    Armenta-Salinas, Concepción / Guzmán-Mejía, Ramón / García-Gutiérrez, Hugo A / Román-Marín, Luisa U / Hernández-Hernández, Juan D / Cerda-García-Rojas, Carlos M / Joseph-Nathan, Pedro

    Journal of natural products

    2019  Volume 82, Issue 12, Page(s) 3410–3420

    Abstract: The tricyclic sesquiterpene ( ... ...

    Abstract The tricyclic sesquiterpene (1
    MeSH term(s) Crystallography, X-Ray ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Sesquiterpenes/chemistry ; Spectrum Analysis/methods ; Stereoisomerism
    Chemical Substances Sesquiterpenes ; longipinene (104AN9V5Q1)
    Language English
    Publishing date 2019-11-27
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.9b00784
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Novel Sesquiterpene Skeletons by Multiple Wagner–Meerwein Rearrangements of a Longipinane-1,9-diol Derivative

    Armenta-Salinas, Concepción / Guzmán-Mejía, Ramón / García-Gutiérrez, Hugo A / Román-Marín, Luisa U / Hernández-Hernández, Juan D / Cerda-García-Rojas, Carlos M / Joseph-Nathan, Pedro

    Journal of natural products. 2019 Nov. 27, v. 82, no. 12

    2019  

    Abstract: The tricyclic sesquiterpene (1R,3R,4S,5S,7S,8S,9S,10R,11R)-7,8-diangeloyloxylongipinan-1,9-diol, or rasteviol (7), underwent multiple Wagner–Meerwein molecular rearrangements and several hydride shifts when treated with Et2O–BF3 to generate the six new ... ...

    Abstract The tricyclic sesquiterpene (1R,3R,4S,5S,7S,8S,9S,10R,11R)-7,8-diangeloyloxylongipinan-1,9-diol, or rasteviol (7), underwent multiple Wagner–Meerwein molecular rearrangements and several hydride shifts when treated with Et2O–BF3 to generate the six new compounds (1R,3R,4S,5R,7S,8S,9S,10R,11S)-7,8-diangeloyloxy-1,9-epoxyjiquilpane (8), (1R,3R,4S,5R,7R,8S,9S,11S)-8-angeloyloxy-1,7-epoxyzamor-10(14)-ene (11), (2S,3R,4R,5R,6R,7R,8S,9S,10S)-7,8-diangeloyloxy-6,9-epoxyjanitziane (14), (4R,5R,7S,8S,9S,10S,11S)-7,8-diangeloyloxy-9-hydroxyjiquilp-3(15)-ene (16), (2S,3S,5R,7S,8R,10S,11R)-7,8-diangeloyloxyiratzian-9-one (18), and (2S,3S,5R,10S,11R)-8-angeloyloxyiratzi-7-en-9-one (22), of which 8, 11, 14, and 18 possess new hydrocarbon skeletons. Their structures were determined by 1D and 2D NMR in combination with single-crystal X-ray diffraction analyses of derivatives 10, 15, 20, and 21, which allowed confirmation of their absolute configurations by means of the Flack and Hooft parameters. In addition, some reaction mechanism information was gained from deuterium labeling experiments.
    Keywords X-ray diffraction ; deuterium ; hydrides ; nuclear magnetic resonance spectroscopy ; reaction mechanisms ; sesquiterpenoids
    Language English
    Dates of publication 2019-1127
    Size p. 3410-3420.
    Publishing place American Chemical Society and American Society of Pharmacognosy
    Document type Article
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.9b00784
    Database NAL-Catalogue (AGRICOLA)

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  4. Article: Fungistatic and bacteriostatic activities of alkamides from Heliopsis longipes roots: affinin and reduced amides.

    Molina-Torres, Jorge / Salazar-Cabrera, Carlos Junior / Armenta-Salinas, Concepción / Ramírez-Chávez, Enrique

    Journal of agricultural and food chemistry

    2004  Volume 52, Issue 15, Page(s) 4700–4704

    Abstract: This work demonstrates the fungistatic and bacteriostatic activities of affinin, the main alkamide of Heliopsis longipes (Gray) Blake (Asteraceae) roots and two alkamides obtained by catalytic reduction of affinin: N-isobutyl-2E-decenamide and N-isobutyl- ...

    Abstract This work demonstrates the fungistatic and bacteriostatic activities of affinin, the main alkamide of Heliopsis longipes (Gray) Blake (Asteraceae) roots and two alkamides obtained by catalytic reduction of affinin: N-isobutyl-2E-decenamide and N-isobutyl-decanamide. The bioactivity was tested against Rhizoctonia solani groups AG3 and AG5, Sclerotium rolfsii, Sclerotium cepivorum, Fusarium sp., Vertcillium sp., phytopathogenic fungi; Phytophthora infestans, a phytopathogenic Chromista; Saccharomyces cerevisiae, a nonphytopathogenic ascomycete; and Escherichia coli, Erwinia carotovora, and Bacillus subtilis, bacteria. Affinin, being the primary component of the lipidic fraction, is expected to be responsible for the fungitoxic activity observed in roots of this plant species. Four of the assayed fungi showed an important sensitivity to the presence of affinin: S. rolfsii, S. cepivorum, P. infestans, and R. solani AG-3 and AG-5, displaying a growth inhibition of 100%. S. cerevisiaeshowed a similar growth inhibition with affinin. None of the alkamides obtained by catalytic reduction of affinin showed a fungitoxic activity. Affinin had a definite negative effect on the growth of E. coli and B. subtilis, but E. carotovora carotovora was not sensitive to the highest dose of affinin assayed. N-Isobutyl-2E-decenamide displayed a higher bacteriostatic activity against E. coli and E. carotovora carotovora. In both cases, this alkamide was more potent than affinin. On the other hand, only N-isobutyl-decanamide displayed a significant activity on the growth of B. subtilis.
    MeSH term(s) Alkenes/isolation & purification ; Alkenes/pharmacology ; Amides/isolation & purification ; Amides/pharmacology ; Anti-Bacterial Agents/pharmacology ; Asteraceae/chemistry ; Fungicides, Industrial/pharmacology ; Magnetic Resonance Spectroscopy ; Plant Roots/chemistry ; Polyunsaturated Alkamides
    Chemical Substances Alkenes ; Amides ; Anti-Bacterial Agents ; Fungicides, Industrial ; N-isobutyl-2E-decenamide ; Polyunsaturated Alkamides
    Language English
    Publishing date 2004-07-28
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/jf034374y
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.A 1172: Show issues Location:
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