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  1. Article ; Online: Antibacterial Potent of Acetylated and Non-Acetylated Clove Bud Essential Oils and Their Main Compounds.

    Achraf, Abdou / Fatima Ezzahra, Maaghloud / Fatima Zahra, Moukhfi / Abdoullah, Bimoussa / Nour-Eddine, Chadli / Abdelhakim, Elmakssoudi / Jamal, Jamal Eddine / Mohamed, Dakir

    Chemistry & biodiversity

    2023  Volume 20, Issue 4, Page(s) e202201034

    Abstract: Clove bud is a medicinal plant used traditionally in Asia for the treatment of various disease. Previously, Clove oil is a potential source of an antimicrobial compounds especially vis-a-vis bacterial pathogens. However, the compound responsible for this ...

    Abstract Clove bud is a medicinal plant used traditionally in Asia for the treatment of various disease. Previously, Clove oil is a potential source of an antimicrobial compounds especially vis-a-vis bacterial pathogens. However, the compound responsible for this activity remains to be investigated. Essential oil (EO) clove, acetylated essential oil clove, eugenol, and acetyleugenol were evaluate as an antibacterial potential agent against Staphyloccocus aureus (SE), Escherichia coli (EC) and Pseudomonas aeruginosa (PA). Essential oil containing eugenol was extracted from buds of Eugenia caryophyllata commonly named clove (Syzygium aromaticum (L.) (Family Myrtaceae) by a simple hydrodistillation. The analysis of the essential oils (EOs) using gas chromatography-mass spectrometry (GC-MS) shows eugenol as the major constituent with 70.14 % of the total. The Eugenol was isolated from the EO using chemical treatment. Afterwards, the EO and eugenol were converted to acetylated EO and acetyleugenol, respectively using acetic anhydride. The antibacterial result revealed that all compounds showed a strong activity against the three strains. The Staphyloccocus aureus and Pseudomonas aeruginosa were extremely sensitive against eugenol with an inhibition diameters of 25 mm. The MIC values of eugenol versus S. aureus and P. aeruginosa were 0.58 and 2.32 mg/mL, respectively, while the MIB values were 2.32 mg/mL and 9.28 mg/mL.
    MeSH term(s) Oils, Volatile/pharmacology ; Oils, Volatile/chemistry ; Eugenol/chemistry ; Syzygium/chemistry ; Staphylococcus aureus ; Anti-Bacterial Agents/pharmacology
    Chemical Substances Oils, Volatile ; acetyleugenol (93-28-7) ; Eugenol (3T8H1794QW) ; Anti-Bacterial Agents
    Language English
    Publishing date 2023-03-17
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2139001-0
    ISSN 1612-1880 ; 1612-1872
    ISSN (online) 1612-1880
    ISSN 1612-1872
    DOI 10.1002/cbdv.202201034
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  2. Article ; Online: Discovery of a new Bcl-2 inhibitor through synthesis, anticancer activity, docking and MD simulations.

    Byadi, Said / Abdoullah, Bimoussa / Fawzi, Mourad / Irrou, Ezaddine / Ait Elmachkouri, Younesse / Oubella, Ali / Auhmani, Aziz / Morjani, Hamid / Labd Taha, Mohamed / Robert, Anthony / Aboulmouhajir, Aziz / Ait Itto, Moulay Youssef

    Journal of biomolecular structure & dynamics

    2023  Volume 42, Issue 8, Page(s) 4145–4154

    Abstract: A database of 300 compounds was virtually screened and docked against Bcl-2 protein; the stability of the best-formed complex was evaluated through Molecular dynamics, the top ten compounds with the ... ...

    Abstract A database of 300 compounds was virtually screened and docked against Bcl-2 protein; the stability of the best-formed complex was evaluated through Molecular dynamics, the top ten compounds with the best
    MeSH term(s) Humans ; Molecular Docking Simulation ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/chemical synthesis ; Molecular Dynamics Simulation ; Proto-Oncogene Proteins c-bcl-2/antagonists & inhibitors ; Proto-Oncogene Proteins c-bcl-2/metabolism ; Proto-Oncogene Proteins c-bcl-2/chemistry ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Structure-Activity Relationship ; Drug Discovery ; Protein Binding
    Chemical Substances Antineoplastic Agents ; Proto-Oncogene Proteins c-bcl-2
    Language English
    Publishing date 2023-05-31
    Publishing country England
    Document type Journal Article
    ZDB-ID 49157-3
    ISSN 1538-0254 ; 0739-1102
    ISSN (online) 1538-0254
    ISSN 0739-1102
    DOI 10.1080/07391102.2023.2218934
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  3. Article ; Online: New 1,2,3-Triazoles from (R)-Carvone

    Ali Oubella / Abdoullah Bimoussa / Abdellah N’ait Oussidi / Mourad Fawzi / Aziz Auhmani / Hamid Morjani / Abdelkhalek Riahi / M’hamed Esseffar / Carol Parish / Moulay Youssef Ait Itto

    Molecules, Vol 27, Iss 769, p

    Synthesis, DFT Mechanistic Study and In Vitro Cytotoxic Evaluation

    2022  Volume 769

    Abstract: Aseries of novel 1,4-disubstituted 1,2,3-triazoles were synthesized from an (R)-carvone terminal alkyne derivative via a Cu (I)-catalyzed azide–alkyne cycloaddition reaction using CuSO 4 ,5H 2 O as the copper (II) source and sodium ascorbate as a ... ...

    Abstract Aseries of novel 1,4-disubstituted 1,2,3-triazoles were synthesized from an (R)-carvone terminal alkyne derivative via a Cu (I)-catalyzed azide–alkyne cycloaddition reaction using CuSO 4 ,5H 2 O as the copper (II) source and sodium ascorbate as a reducing agent which reduces Cu (II) into Cu (I). All the newly synthesized 1,2,3-triazoles 9a – h were fully identified on the basis of their HRMS and NMR spectral data and then evaluated for their cell growth inhibition potential by MTS assay against HT-1080 fibrosarcoma, A-549 lung carcinoma, and two breast adenocarcinoma (MCF-7 and MDA-MB-231) cell lines. Compound 9d showed notable cytotoxic effects against the HT-1080 and MCF-7 cells with IC 50 values of 25.77 and 27.89 µM, respectively, while compound 9c displayed significant activity against MCF-7 cells with an IC 50 value of 25.03 µM. Density functional calculations at the B3LYP/6-31G* level of theory were used to confirm the high reactivity of the terminal alkyne as a dipolarophile. Quantum calculations were also used to investigate the mechanism of both the uncatalyzed and copper (I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC). The catalyzed reaction gives complete regioselectivity via a stepwise mechanism streamlining experimental observations. The calculated free-energy barriers 4.33 kcal/mol and 29.35 kcal/mol for the 1,4- and 1,5-regioisomers, respectively, explain the marked regioselectivity of the CuAAC reaction.
    Keywords (R)-carvone ; 1,2,3-triazole ; DFT calculations ; regioselectivity ; cytotoxic activity ; Organic chemistry ; QD241-441
    Subject code 540
    Language English
    Publishing date 2022-01-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
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  4. Article ; Online: (1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecane

    Abdoullah Bimoussa / Aziz Auhmani / My Youssef Ait Itto / Jean-Claude Daran / Abdelwahed Auhmani

    Acta Crystallographica Section E, Vol 70, Iss 4, Pp o480-o

    2014  Volume 480

    Abstract: The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-ene with metachloroperbenzoic acid. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a ... ...

    Abstract The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-ene with metachloroperbenzoic acid. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.
    Keywords Chemistry ; QD1-999 ; Science ; Q
    Language English
    Publishing date 2014-04-01T00:00:00Z
    Publisher International Union of Crystallography
    Document type Article ; Online
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  5. Article ; Online: (1R,3S,8R)-3,7,7,10-Tetramethyltricyclo[6.4.0.01,3]dodec-9-en-11-one

    Abdoullah Bimoussa / Aziz Auhmani / My Youssef Ait Itto / Jean-Claude Daran / Auhmani Abdelwahed

    Acta Crystallographica Section E, Vol 70, Iss 1, Pp o81-o

    2014  Volume 82

    Abstract: The absolute configuration of the title compound, C16H24O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair ... ...

    Abstract The absolute configuration of the title compound, C16H24O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair conformation. In the crystal, there is a weak C—H.O hydrogen bond between the methylene group of the cyclopropane ring and the carbonyl group of a screw-axis-related molecule, which builds up a zigzag-like chain along the b-axis direction.
    Keywords Chemistry ; QD1-999
    Language English
    Publishing date 2014-01-01T00:00:00Z
    Publisher International Union of Crystallography
    Document type Article ; Online
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  6. Article ; Online: Crystal structure of (1S,3R,8R,9R)-2,2-dichloro-3,7,7-trimethyl-10-methylenetricyclo[6.4.0.01,3]dodecan-9-ol

    Ahmed Benzalim / Aziz Auhmani / Abdoullah Bimoussa / My Youssef Ait Itto / Jean-Claude Daran / Abdelwahed Auhmani

    Acta Crystallographica Section E: Crystallographic Communications, Vol 72, Iss 8, Pp 1163-

    2016  Volume 1166

    Abstract: The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-dichloro-3,7,7,10-tetramethyl-9,10-epoxytricyclo[6.4.0.01,3]dodecane with a concentrated solution of hydrobromic acid. It is built up from three fused rings: a cycloheptane ...

    Abstract The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-dichloro-3,7,7,10-tetramethyl-9,10-epoxytricyclo[6.4.0.01,3]dodecane with a concentrated solution of hydrobromic acid. It is built up from three fused rings: a cycloheptane ring, a cyclohexyl ring bearing alkene and hydroxy substituents, and a cyclopropane ring bearing two chlorine atoms. The asymmetric unit contains two molecules linked by an O—H.O hydrogen bond. In the crystal, further O—H.O hydrogen bonds build up an R44(8) cyclic tetramer. One of the molecules presents disorder that affects the seven-membered ring. In both molecules, the six-membered rings display a chair conformation, whereas the seven-membered rings display conformations intermediate between boat and twist-boat for the non-disordered molecule and either a chair or boat and twist-boat for the disordered molecule owing to the disorder. The absolute configuration for both molecules is 1S,3R,8R,9R and was deduced from the chemical pathway and further confirmed by the X-ray structural analysis.
    Keywords crystal structure ; absolute configuration ; sesquiterpenes ; asymmetric synthesis ; natural products ; Chemistry ; QD1-999
    Subject code 540
    Language English
    Publishing date 2016-08-01T00:00:00Z
    Publisher International Union of Crystallography
    Document type Article ; Online
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  7. Article ; Online: Absolute configuration of (1S,3R,8R)-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

    Abdoullah Bimoussa / Aziz Auhmani / My Youssef Ait Itto / Jean-Claude Daran / Abdelwahed Auhmani

    Acta Crystallographica Section E, Vol 69, Iss 11, Pp o1692-o

    2013  Volume 1693

    Abstract: The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven- ... ...

    Abstract The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The molecular packing within the crystal is stabilized only by van der Waals interactions.
    Keywords Chemistry ; QD1-999
    Language English
    Publishing date 2013-11-01T00:00:00Z
    Publisher International Union of Crystallography
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  8. Article: Absolute configuration of (1R,3S,8R,11R)-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-ol.

    Abdoullah, Bimoussa / Aziz, Auhmani / Ait Itto, My Youssef / Daran, Jean-Claude / Abdelwahed, Auhmani

    Acta crystallographica. Section E, Structure reports online

    2013  Volume 69, Issue Pt 8, Page(s) o1308–9

    Abstract: The absolute configuration of the title compound, C16H26O, was determined as (1R,3S,8R,11R) based mainly on the synthetic pathway but is also implied by the X-ray analysis. The mol-ecule contains fused six- and seven-membered rings. Part of the seven- ... ...

    Abstract The absolute configuration of the title compound, C16H26O, was determined as (1R,3S,8R,11R) based mainly on the synthetic pathway but is also implied by the X-ray analysis. The mol-ecule contains fused six- and seven-membered rings. Part of the seven-membered ring was refined as disordered over two sets of sites with the occupancy ratio fixed at 0.86:0.14. The disorder corresponds to a major chair conformation and a minor boat conforation. In the crysyal, O-H⋯O hydrogen bonds connect the mol-ecules into chains parallel to the a axis.
    Language English
    Publishing date 2013-07-24
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2041947-8
    ISSN 1600-5368
    ISSN 1600-5368
    DOI 10.1107/S1600536813018497
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