147127-74-0

Upstream product

• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 
• 1504-55-8 2-methyl-3-phenylprop-2-en-1-ol 
• 100-52-7 benzaldehyde 
• 21370-57-0 methyl 2-methyl-3-phenylacrylate 
• 1199-77-5 α-methylcinnamic acid 
• 7042-33-3 ethyl 2-methylcinnamate 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 

Downstream Products

• 110379-56-1 (R)-((S)-4-Methyl-[1,3]dioxolan-4-yl)-phenyl-methanol 
• 76638-09-0 trans-2-methyl-3-phenyloxirane-2-carbaldehyde 
• 57502-36-0 3-methyl-2-phenylbut-3-en-1-ol 
• 90926-14-0 rac-2-methyl-3-phenyl-1,2-propanediol 
• 14366-91-7 syn-2-methyl-1-phenyl-1,3-propanediol 
• 959628-18-3 2-methyl-3-phenyloxirane-2-carbaldehyde 
• 102285-75-6 isopropyl (2SR,3SR)-2-methyl-3-hydroxy-3-phenylpropionate 

Relevant academic research and scientific papers

Nanosheet-enhanced enantioselectivity in the vanadium-catalyzed asymmetric epoxidation of allylic alcohols

The use of suitable chiral ligands is an efficient means of producing highly enantioselective transition-metal catalysts. Herein, we report a facile, economic, and effective strategy for the design of chiral ligands that demonstrate enhanced enantioselectivity and catalytic efficacy. Our simple strategy employs naturally occurring or synthetic inorganic nanosheets as huge and rigid planar substituents for, but not limited to, naturally available α-amino-acid ligands; these ligands were successfully used in the vanadium-catalyzed asymmetric epoxidation of allylic alcohols. The crucial role of the inorganic nanosheets as planar substituents in improving the enantioselectivity of the reaction was clearly revealed by relating the observed enantiomeric excess with the distribution of the catalytic centers and the accessibility of the substrate molecules to the catalytic sites. DFT calculations indicated that the LDH layer improved the enantioselectivity by influencing the formation and stability of the catalytic transition states, both in terms of steric resistance and H-bonding interactions. Handy tricks for asymmetric catalysis: The inorganic layer serves as a huge and rigid planar substituent to effectively enhance the enantioselectivity in the vanadium-catalyzed asymmetric epoxidation of allylic alcohols. Copyright

Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives

Marine natural products derived from special or extreme environment provide an important source for the development of anti-tumor drugs due to their special skeletons and functional groups. In this study, based on our previous work on the total synthesis and structure revision of the novel marine natural product Chrysamide B, a group of its derivatives were designed, synthesized, and subsequently of which the anti-cancer activity, structure-activity relationships and cellular mechanism were explored for the first time. Compared with Chrysamide B, better anti-cancer performance of some derivatives against five human cancer cell lines (SGC-7901, MGC-803, HepG2, HCT-116, MCF-7) was observed, especially for compound b-9 on MGC-803 and SGC-7901 cells with the IC 50 values of 7.88 ± 0.81 and 10.08 ± 1.08 μM, respectively. Subsequently, cellular mechanism study suggested that compound b-9 treatment could inhibit the cellular proliferation, reduce the migration and invasion ability of cells, and induce mitochondrial-dependent apoptosis in gastric cancer MGC-803 and SGC-7901 cells. Furthermore, the mitochondrial-dependent apoptosis induced by compound b-9 is related with the JAK2/STAT3/Bcl-2 signaling pathway. To conclude, our results offer a new structure for the discovery of anti-tumor lead compounds from marine natural products.

Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation

Inflammation as a host's excessive immune response to stimulation, is involved in the development of numerous diseases. To discover novel anti-inflammatory agents and based on our previous synthetic work on marine natural product Chrysamide B, it and a series of derivatives were synthesized and evaluated for their anti-inflammatory activity on inhibition of LPS-induced NO production. Then the preliminary structure–activity relationships were conducted. Among them, Chrysamide B is the most potent anti-inflammatory agent with low cytotoxicity and strong inhibition on the production of NO (IC50 = 0.010 μM) and the activity of iNOS (IC50 = 0.082 μM) in LPS-stimulated RAW 264.7 cells. Primary studies suggested that the mechanism of action may be that it interfered the formation of active dimeric iNOS but not affected transcription and translation. Furthermore, its good performance of anti-inflammatory effect on LPS-induced multiple inflammatory cytokines production, carrageenan-induced paw edema, and endotoxin-induced septic mice, was observed. We believe that these findings would provide an idea for the further modification and research of these analogs in the future.

Chrysamide B derivative with anti-tumor activity and preparation and application of Chrysamide B derivative

The invention belongs to the field of medicinal chemistry, and particularly relates to a marine natural product Chrysamide B and a derivative thereof. The marine natural product Chrysamide B comprisesstereoisomers or pharmaceutically acceptable salts, solvates and prodrugs of the marine natural product Chrysamide B, general formulas are shown in a formula (I), a formula (II) and a formula (III).The invention also provides preparation and application of the compound. The compound has an anti-cancer effect; the compound has good inhibitory activity on digestive system cancers, leukemia, livertumors, non-small cell lung cancers, cervical cancers, breast cancers and the like and has the effects of inducing tumor cell apoptosis, activating apoptosis protein expression, retarding cycle, inhibiting proliferation and the like and is a potential antitumor drug.

Recoverable polystyrene-supported catalysts for Sharpless allylic alcohols epoxidations

In this work, new heterogeneous catalysts intended for enantioselective Sharpless epoxidation were prepared. The catalysts are based on Ti(IV) complexes of cross-linked swellable spherical copolymer beads of styrene with ethyl-(4-vinylbenzyl)-L-tartrate, or with ethyl-(2R,3R)-2,3-dihydroxy-4-oxo-5-(4-vinylphenyl)pentanoate. These catalysts were tested in epoxidation of cinnamyl alcohols. High conversion (up to 99%) and high enantioselectivity (up to 99% ee) were achieved in the case of catalysts based on copolymers of styrene with ethyl-(4-vinylbenzyl)-L-tartrate (5, 20, 50%). Unfortunately, the copolymers lost their enantioselectivity due to the leaching of L-tartrate, caused by alcoholysis of ester bond. This problem has been overcome by replacing the ester bond by a stable keto bond. The prepared catalyst based on the copolymer of styrene with ethyl-(2R,3R)-2,3-dihydroxy-4-oxo-5-(4-vinylphenyl)pentanoate (20%) achieved a similarly high conversion and enantioselectivity as in the previous case (up to 99%, up to 99% ee) and was successfully recycled.

Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide

A simple, efficient, and environmentally friendly asymmetric epoxidation of primary, secondary, tertiary allylic, and homoallylic alcohols has been accomplished. This process was promoted by a tungsten-bishydroxamic acid complex at room temperature with the use of aqueous 30% H2O2 as oxidant, yielding the products in 84-98% ee.

Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: An entry to virtually enantiopure amino alcohols

The first catalytic enantioselective aminolysis of trans-2,3-epoxy alcohols has been accomplished. This stereo-specific ring-opening process was efficiently promoted by a tungsten/bis(hydroxamic acid) catalytic system, furnishing various anti-3-amino-1,2-diols with excellent regiocontrol and high enantioselectivities (up to 95% ee). Moreover, virtually enantiopure 3-amino-1,2-diols could be obtained by the sequential combination of two reactions that both involve the use of a chiral catalyst.

Highly enantioselective and efficient asymmetric epoxidation catalysts: Inorganic nanosheets modified with α-amino acids as ligands

Layered catalyst: The attachment of α-amino acid ligands to inorganic nanosheets for use as ligands to vanadium, resulted in a catalyst that enhanced the enantioselectivity of the epoxidation of allylic alcohols (see picture). The catalyst can be colloidized, allowing for the catalytic reactions to be carried out under pseudo-homogeneous reaction conditions and also the catalysts to be directly recycled by simple liquid/liquid separation. Copyright

Oxidation catalysis of Nb(salan) complexes: Asymmetric epoxidation of allylic alcohols using aqueous hydrogen peroxide as an oxidant

Several optically active Nb(salan) complexes were synthesized, and their oxidation catalysis was examined. A dimeric μ-oxo Nb(salan) complex that was prepared from Nb(OiPr)5 and a salan ligand was found to catalyze the asymmetric epoxidation of allylic alcohols using a urea-hydrogen peroxide adduct as an oxidant with good enantioselectivity. However, subsequent studies of the time course of this epoxidation and of the relationship between the ee of the ligand and the ee of the product indicated that the μ-oxo dimer dissociates into a monomeric species prior to epoxidation. Moreover, monomeric Nb(salan) complexes prepared in situ from Nb(OiPr)5 and salan ligands followed by water treatment were found to catalyze the epoxidation of allylic alcohols better using aqueous hydrogen peroxide in CHCl3/brine or toluene/brine solution with high enantioselectivity ranging from 83 to 95% ee, except for the reaction of cinnamyl alcohol that showed a moderate ee of 74%. This is the first example of the highly enantioselective epoxidation of allylic alcohols using aqueous hydrogen peroxide as an oxidant.

Modification of chiral dimethyl tartrate through transesterification: Immobilization on POSS and enantioselectivity reversal in sharpless asymmetric epoxidation

Modification of dimethyl tartrate has been investigated through transesterification with aminoalcohols to provide reactive functionalities for the covalent bonding of chiral tartrate to polyhedral oligomeric silsesquioxanes. The transesterification of dimethyl tartrate has been widely studied using different catalytic systems and reaction conditions. Through the proper selection of both the catalytic system and the reaction conditions, it is possible to achieve monosubstituted or bis-substituted tartrate derivatives as sole products. All the intermediate chiral tartrate-derived ligands were successfully used in the homogeneous enantioselective epoxidation of allylic alcohols providing moderate enantiomeric excess over the products. Attached amine groups have been used to support the modified tartrate ligands on to a haloaryl-functionalized silsesquioxane moiety. This final chiral tartrate ligand displays reverse enantioselectivity in the asymmetric epoxidation of allylic alcohols with regard to the starting dimethyl tartrate ligand, both molecules having the same chiral sign. However, the POSS-containing ligand can be easily recovered in almost quantitative yield and reused in asymmetric epoxidation reactions. In addition, recovered silsesquioxane-pendant ligand, though displaying decreasing catalytic activity in recycling epoxidation tests, showed very stable enantioselective behavior.