629-90-3Relevant articles and documents
In silico, cytotoxic and antioxidant potential of novel ester, 3-hydroxyoctyl -5- trans-docosenoate isolated from anchusa arvensis (L.) m.bieb. against hepg-2 cancer cells
Hussain, Sajid,Ullah, Farhat,Ayaz, Muhammad,Ali Shah, Syed Adnan,Shah, Azhar-Ul-Haq Ali,Shah, Syed Majid,Wadood, Abdul,Aman, Waqar,Ullah, Riaz,Shahat, Abdelaaty A.,Nasr, Fahd A.
, p. 4195 - 4205 (2019)
Background: Cancer is one of the chronic health conditions worldwide. Various therapeutically active compounds from medicinal plants were the current focus of this research in order to uncover a treatment regimen for cancer. Anchusa arvensis (A. anchusa) (L.) M.Bieb. contains many biologically active compounds. Methods: In the current study, new ester 3-hydroxyoctyl-5-trans-docosenoate (compound-1) was isolated from the chloroform soluble fraction of A. anchusa using column chromato-graphy. Using MTT assay, the anticancer effect of the compound was determined in human hepatocellular carcinoma cells (HepG-2) compared with normal epithelial cell line (Vero). DPPH and ABTS radical scavenging assays were performed to assess the antioxidant potential. The Molecular Operating Environment (MOE-2016) tool was used against tyrosine kinase. Results: The structure of the compound was elucidated based on IR, EI, and NMR spectroscopy technique. It exhibited a considerable cytotoxic effect against HepG-2 cell lines with IC50 value of 6.50 ± 0.70 μg/mL in comparison to positive control (doxorubicin) which showed IC50 value of 1.3±0.21 μg/mL. The compound did not show a cytotoxic effect against normal epithelial cell line (Vero). The compound also exhibited significant DPHH scavenging ability with IC50 value of 12 ± 0.80 μg/mL, whereas ascorbic acid, used as positive control, demonstrated activity with IC50 = 05 ± 0.15 μg/mL. Similarly, it showed ABTS radical scavenging ability (IC50 = 130 ± 0.20 μg/mL) compared with the value obtained for ascorbic acid (06 ± 0.85 μg/mL). In docking studies using MOE-2016 tool, it was observed that compound-1 was highly bound to tyrosine kinase by having two hydrogen bonds at the hinge region. This good bonding network by the compound might be one of the reasons for showing significant activity against this enzyme. Conclusion: Our findings led to the isolation of a new compound from A. anchusa which has significant cytotoxic activity against HepG-2 cell lines with marked antioxidant potential.
Cerium(IV) Carboxylate Photocatalyst for Catalytic Radical Formation from Carboxylic Acids: Decarboxylative Oxygenation of Aliphatic Carboxylic Acids and Lactonization of Aromatic Carboxylic Acids
Hirosawa, Keishi,Mashima, Kazushi,Satoh, Tetsuya,Shinohara, Koichi,Shirase, Satoru,Tamaki, Sota,Tsurugi, Hayato
supporting information, (2020/03/25)
We found that in situ generated cerium(IV) carboxylate generated by mixing the precursor Ce(OtBu)4 with the corresponding carboxylic acids served as efficient photocatalysts for the direct formation of carboxyl radicals from carboxylic acids under blue light-emitting diodes (blue LEDs) irradiation and air, resulting in catalytic decarboxylative oxygenation of aliphatic carboxylic acids to give C-O bond-forming products such as aldehydes and ketones. Control experiments revealed that hexanuclear Ce(IV) carboxylate clusters initially formed in the reaction mixture and the ligand-to-metal charge transfer nature of the Ce(IV) carboxylate clusters was responsible for the high catalytic performance to transform the carboxylate ligands to the carboxyl radical. In addition, the Ce(IV) carboxylate cluster catalyzed direct lactonization of 2-isopropylbenzoic acid to produce the corresponding peroxy lactone and ?3-lactone via intramolecular 1,5-hydrogen atom transfer (1,5-HAT).
On/Off O2 Switchable Photocatalytic Oxidative and Protodecarboxylation of Carboxylic Acids
Bazyar, Zahra,Hosseini-Sarvari, Mona
, p. 13503 - 13515 (2019/10/11)
Photoredox catalysis in recent years has manifested a powerful branch of science in organic synthesis. Although merging photoredox and metal catalysts has been a widely used method, switchable heterogeneous photoredox catalysis has rarely been considered. Herein, we open a new window to use a switchable heterogeneous photoredox catalyst which could be turned on/off by changing a simple stimulus (O2) for two opponent reactions, namely, oxidative and protodecarboxylation. Using this strategy, we demonstrate that Au@ZnO core-shell nanoparticles could be used as a switchable photocatalyst which has good catalytic activity to absorb visible light due to the localized surface plasmon resonance effect of gold, can decarboxylate a wide range of aromatic and aliphatic carboxylic acids, have multiple reusability, and are a reasonable candidate for synthesizing both aldehydes/ketones and alkane/arenes in a large-scale set up. Some biologically active molecules are also shown via examples of the direct oxidative and protodecarboxylation which widely provided pharmaceutical agents.
Pillar5arenes as Supramolecular Hosts in Aqueous Biphasic Rhodium-Catalyzed Hydroformylation of Long Alkyl-chain Alkenes
Benatmane, Missipssa,Cousin, Kévin,Laggoune, Nérimel,Menuel, Stéphane,Monflier, Eric,Woisel, Patrice,Hapiot, Frédéric,Potier, Jonathan
, p. 5306 - 5313 (2018/11/10)
Aqueous biphasic catalysis continues to attract strong interest, especially when very hydrophobic substrates are concerned. Indeed, their insolubility in water strongly limit their transformation by water-soluble organometallic catalysts. To improve contacts between the substrate-containing organic phase and the catalyst-containing phase, one of the best solutions consists in using interfacial additives capable of supramolecularly recognize the substrate and/or the catalyst. In the present study, modified pillar5arenes are considered as interfacial additives and their performance is assessed in Rh-catalyzed hydroformylation of long alkyl-chain alkenes (higher olefins). Pillar5arenes substituted by carboxylate functions and methyl groups P5 A-(Me)10-x-(CH2COOMe)x are compared to pillar5arenes substituted by polyethylene glycol (PEG) chains (P5 A-(Me)5-(PEG)5 and P5 A-(PEG)10). Utilization of P5 A-(Me)10-x-(CH2COOMe)x leads to high conversion and regioselectivity (linear/branched aldehyde ratio) in Rh-catalyzed hydroformylation of 1-decene and 1-hexadecene. Compared with other interfacial additives such as modified cyclodextrins, the studied pillar5arenes show lower chemo-selectivity, similar catalytic activity and higher regioselectivity.
Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst
Zhang, Mengqi,Zhai, Yongyan,Ru, Shi,Zang, Dejin,Han, Sheng,Yu, Han,Wei, Yongge
supporting information, p. 10164 - 10167 (2018/09/13)
Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.
Water-soluble phosphane-substituted cyclodextrin as an effective bifunctional additive in hydroformylation of higher olefins
Leblond,Potier,Menuel,Bricout,Machut-Binkowski,Landy,Tilloy,Monflier,Hapiot
, p. 3823 - 3830 (2017/09/07)
In cyclodextrin (CD)-mediated aqueous biphasic catalysis, favoring contacts between the CD ("host"), the organic substrate ("guest") and the water-soluble catalyst is crucial for the reaction to proceed efficiently at the aqueous/organic interface. Grafting the catalyst onto the CD backbone thus appears as an attractive approach to favor the molecular recognition of the substrate and its subsequent catalytic conversion into products. In this context, a new water-soluble β-CD-based phosphane was synthesized and characterized by NMR, tensiometric and ITC measurements. The β-CD-based phosphane consisted of a 3,3′-disulfonatodiphenyl phosphane connected to the primary face of β-CD by a dimethyleneamino spacer. Intra- and intermolecular inclusion processes of one of the two sulfophenyl groups into the β-CD cavity were identified in water. However, the association constant (Ka) related to the β-CD/sulfophenyl group couple was low. Accordingly, the inclusion process was easily displaced upon coordination to rhodium complexes. The efficacy of the resulting Rh-complex coordinated by β-CD-based phosphanes was assessed in Rh-catalyzed hydroformylation of higher olefins. The catalytic system proved to be far more successful and efficient than a system consisting of supramolecularly interacting phosphanes and CDs. The catalytic activity was up to 30-fold higher while the chemo- and regioselectivities remain rather unchanged.
Sequential reactions from catalytic hydroformylation toward the synthesis of amino compounds
Almeida, Ana R.,Carrilho, Rui M.B.,Peixoto, Andreia F.,Abreu, Artur R.,Silva, Artur,Pereira, Mariette M.
supporting information, p. 2389 - 2395 (2017/04/03)
Different families of new amino compounds were efficiently synthesized, through optimized sequential processes, involving rhodium catalyzed hydroformylation as the key step. The selection of appropriate hydroformylation catalytic systems and reaction conditions allowed obtaining aldehydes derived from several n-alkyl olefins, cholest-4-ene and 3-vinyl-1H-indole, which were subsequently transformed, in one-pot, in to α-amino acids via hydroformylation/Strecker reaction, and in to tertiary amines via hydroaminomethylation, with excellent yields.
Thermal stability, decomposition enthalpy, and Raman spectroscopy of 1-alkene secondary ozonides
Cataldo, Franco
, p. 994 - 998 (2015/02/19)
The synthesis of a series of 1-alkene secondary ozonides was monitored with Raman spectroscopy which is very effective in the detection of the O-O stretching band of the 1,2,4-trioxolane ring. The 1-alkene secondary ozonides thermal decomposition was studied with DSC (differential scanning calorimetry). For all ozonides studied the decomposition onset was found at about 106 °C and the decomposition peak at about 130 °C. The decomposition enthalpy ΔHdec of the secondary ozonides examined was found in the range of -313 to -347 kJ/mol. Despite the considerable amount of heat evolved, the decomposition was not explosive. The decomposition products of 1-octadecene ozonide were studied by TGA-FTIR (thermogravimetric analysis coupled with FT-infrared spectroscopy) and by GC-MS. The main products detected were formic acid and heptadecanal.
RP-HPLC-fluorescence analysis of aliphatic aldehydes: Application to aldehyde-generating enzymes HACL1 and SGPL1
Mezzar, Serena,De Schryver, Evelyn,Van Veldhoven, Paul P.
, p. 573 - 582 (2014/03/21)
Long-chain aldehydes are commonly produced in various processes, such as peroxisomal α-oxidation of long-chain 3-methyl-branched and 2-hydroxy fatty acids and microsomal breakdown of phosphorylated sphingoid bases. The enzymes involved in the aldehyde-generating steps of these processes are 2-hydroxyacyl-CoA lyase (HACL1) and sphingosine-1-phosphate lyase (SGPL1), respectively. In the present work, nonradioactive assays for these enzymes were developed employing the Hantzsch reaction. Tridecanal (C13-al) and heptadecanal (C17-al) were selected as model compounds and cyclohexane-1,3-dione as 1,3-diketone, and the fluorescent derivatives were analyzed by reversed phase (RP)-HPLC. Assay mixture composition, as well as pH and heating, were optimized for C13-al and C17-al. Under optimized conditions, these aldehydes could be quantified in picomolar range and different long-chain aldehyde derivatives were well resolved with a linear gradient elution by RPHPLC. Aldehydes generated by recombinant enzymes could easily be detected via this method. Moreover, the assay allowed to document activity or deficiency in tissue homogenates and fibroblast lysates without an extraction step. In conclusion, a simple, quick, and cheap assay for the study of HACL1 and SGPL1 activities was developed, without relying on expensive mass spectrometric detectors or radioactive substrates. Copyright
Synergetic effect of randomly methylated β-cyclodextrin and a supramolecular hydrogel in Rh-catalyzed hydroformylation of higher olefins
Potier, Jonathan,Menuel, Stephane,Monflier, Eric,Hapiot, Frederic
, p. 2342 - 2346 (2014/07/21)
A significant improvement in Rh-catalyzed hydroformylation of very hydrophobic alkenes was achieved using a biphasic catalytic system consisting of a substrate-containing organic phase and a catalyst-containing hydrogel phase [consisting of poly(ethylene glycol) 20000 (PEG20000) and α-cyclodextrin (α-CD)]. The catalytic performance of the Pickering emulsion that resulted from the formation of α-CD/PEG20000 crystallites at the oil droplet surface proved to be greatly dependent upon the presence of additives. We showed that controlled uploads of randomly methylated β-cyclodextrin (RAME-β-CD) within the supramolecular hydrogel could positively affect both the catalytic activity and chemoselectivity of the hydroformylation reaction. Conversely, no Pickering emulsion could be observed using excess RAME-β-CD, resulting in the subsequent degradation of the catalytic performance. Optical microscopy and optical fluorescence microscopy supported the catalytic results and allowed us to explain the role of RAME-β-CD. Indeed, controlled uploads of RAME-β-CD prevented the saturation of the oil droplet surface. RAME-β-CD acted as a fluidifier of the Pickering emulsion and accelerated the dynamics of exchange between the substrate-containing organic phase and the catalyst-containing hydrogel phase. Morever, RAME-β-CD acted as a receptor that participated in the conversion of the alkene by supramolecular means.
