79822-65-4

Upstream product

• 107-05-1 3-chloroprop-1-ene 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 556-56-9 allyl iodid 
• 106-95-6 allyl bromide 
• 71186-67-9 3,4-diallyloxybenzaldehyde 
• 107-18-6 allyl alcohol 
• 1198160-11-0 4-allyloxy-3-((2-(trimethylsilyl)ethoxy)methoxy)benzaldehyde 
• 875155-64-9 C₁₇H₂₄N₆O₅S 
• 1198160-10-9 4-hydroxy-3-((2-(trimethylsilyl)ethoxy)methoxy)benzaldehyde 

Downstream Products

• 79822-66-5 3,4-dihydroxy-5-(prop-2-enyl)benzaldehyde 
• 347894-32-0 4-Allyloxy-3-[D₃]methoxybenzaldehyde 
• 195327-48-1 4-allyloxy-3-benzyloxybenzaldehyde 
• 863481-48-5 (4-allyloxy-3-benzyloxyphenyl)methanol 
• 863481-49-6 2-(4-allyloxy-3-benzyloxybenzyloxy)tetrahydropyran 
• 347894-33-1 (4-Allyloxy-3-[D₃]methoxyphenyl)methanol 
• 347894-36-4 2-[D₃]Methoxy-4-(tetrahydropyran-2-yloxymethyl)phenol 
• 347894-44-4 [4-(2-[D₄]Iodoethoxy)-3-[D₃]methoxyphenyl]methanol 
• 347894-35-3 2-(4-Allyloxy-3[D₃]methoxybenzyloxy)tetrahydropyran 
• 347894-37-5 2-[4-(2-[D₄]Bromoethoxy)-3-[D₃]methoxybenzyloxy]tetrahydropyran 
• 347894-41-1 2-[4-(2-[D₄]Iodoethoxy)-3-[D₃]methoxybenzyloxy]tetrahydropyran 
• 347894-50-2 12-[2-(4-Hydroxymethyl-2-[D₃]methoxyphenoxy)-[D₄]ethoxy]-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol 
• 347894-52-4 {3-[D₃]Methoxy-4-[2-(3,8,13-trimethoxy-7,12-bis{2-[2-methoxy-4-(tetrahydropyran-2-yloxymethyl)phenoxy]-[D₄]ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-yloxy)-[D₄]ethoxy]phenyl}methanol 
• 1447760-18-0 [2-(2,3-bisnitrooxypropoxy)-5-formylphenyl] 3-(tert-butoxycarbonylamino)propanoate 

Relevant academic research and scientific papers

Directed Evolution of a Halide Methyltransferase Enables Biocatalytic Synthesis of Diverse SAM Analogs

Biocatalytic alkylations are important reactions to obtain chemo-, regio- and stereoselectively alkylated compounds. This can be achieved using S-adenosyl-l-methionine (SAM)-dependent methyltransferases and SAM analogs. It was recently shown that a halide methyltransferase (HMT) from Chloracidobacterium thermophilum can synthesize SAM from SAH and methyl iodide. We developed an iodide-based assay for the directed evolution of an HMT from Arabidopsis thaliana and used it to identify a V140T variant that can also accept ethyl-, propyl-, and allyl iodide to produce the corresponding SAM analogs (90, 50, and 70 % conversion of 15 mg SAH). The V140T AtHMT was used in one-pot cascades with O-methyltransferases (IeOMT or COMT) to achieve the regioselective ethylation of luteolin and allylation of 3,4-dihydroxybenzaldehyde. While a cascade for the propylation of 3,4-dihydroxybenzaldehyde gave low conversion, the propyl-SAH intermediate could be confirmed by NMR spectroscopy.

NOVEL BENZYLIDENEACETONE DERIVATIVE AND USE THEREOF

The present invention relates to novel benzylideneacetone derivatives or uses thereof, more specifically, the present invention relates to a pharmaceutical composition for preventing or treating, or food composition for ameliorating a cancer or a bone disease comprising a compound defined by Formula 1 or pharmaceutically acceptable salt thereof as an active ingredient. Since compounds according to the present invention exhibit strong inhibitory activity on proliferation and differentiation of osteoclast, and activity on proliferation and differentiation of osteoblast, it can be usefully used to develop safe and effective anti-cancer agents, and therapeutic agents for preventing and treating or foods for ameliorating bone diseases including osteoporosis, and the like.

Enantiopure C1-Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents

Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial

Benzylideneacetone Derivatives Inhibit Osteoclastogenesis and Activate Osteoblastogenesis Independently Based on Specific Structure-Activity Relationship

(E)-3,4-Dihydroxybenzylideneacetone (compound 1) inhibited receptor activator of NF-κB ligand-induced osteoclastogenesis of C57BL/6 bone marrow monocyte/macrophages with IC50 of 7.8 μM (IC50 of alendronate, 3.7 μM) while stimulating the differentiation of MC3T3-E1 osteoblastic cells, accompanied by the induction of Runt-related transcription factor 2, alkaline phosphatase, and osteocalcin. (E)-4-(3-Hydroxy-4-methoxyphenyl)-3-buten-2-one (compound 2c) showed a dramatically increased osteoclast-inhibitory potency with IC50 of 0.11 μM while sustaining osteoblast-stimulatory activity. (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one (compound 2g) stimulated alkaline phosphatase production 2-fold at 50 μM without changing osteoclast-inhibitory activity, compared with compound 1. Oral administration of compounds 1, 2c, and 2g prevented ovariectomy-induced osteoporosis in ddY mice to a degree proportional to their osteoclastogenesis-inhibitory potencies. The administration of 1 (mg/kg)/d compound 2c ameliorated histomorphometry of osteoporotic bone to a degree comparable with 10 (mg/kg)/d alendronate. Conclusively, the in vitro capacity of a few benzylideneacetone derivatives to inhibit osteoclastogenesis supported by independent osteoblastogenesis activation was convincingly reflected in in vivo management of osteoporosis, suggesting a potential novel therapeutics for osteopenic diseases.

Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde

Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.

Synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside

The invention belongs to the field of synthesizing of compounds, and particularly relates to a synthesizing method of piceatannol 3'-O-belta-D-glucopyranoside. The synthesizing method is characterized in that a compound in a formula VIII is reacted, so as to obtain the piceatannol 3'-O-belta-D-glucopyranoside shown in a formula I, wherein in the formula VIII, R is acetyl, benzyl, allyl or alloc. The synthesizing method has the advantages that the compound of piceatannol 3'-O-belta-D-glucopyranoside is synthesized; the cost of the used reagent is low, and the obtaining is easy; the operation is simple, and the total yield rate is 26%; a simple, efficient and environment-friendly piceatannol 3'-O-belta-D-glucopyranoside synthesizing route is provided, a first path is opened for the chemical synthesizing of the piceatannol 3'-O-belta-D-glucopyranoside, and the important meaning is realized in the field of medicines. The formula I and the formula VIII are shown in the description.

Enzymatic allylation of catechols

Enzymatic allylation of catechols was realized via catechol O-methyltransferase (COMT) using an allylated S-adenosyl- L-methionine (allyl-SAM) analog, with relatively good chemoand regioselectivities. This new reaction offered an alternative procedure for allylation of catechols, which can be expanded as a biocatalytic allylation method in organic synthesis.

Water-soluble nitric-oxide-releasing acetylsalicylic acid (ASA) prodrugs

A series of water-soluble (benzoyloxy)methyl esters of acetylsalicylic acid (ASA), commonly known as aspirin, are described. The new derivatives each have alkyl chains containing a nitric oxide (NO)-releasing nitrooxy group and a solubilizing moiety bonded to the benzoyl ring. The compounds were synthesized and evaluated as ASA prodrugs. After conversion to the appropriate salt, most of the derivatives are solid at room temperature and all possess good water solubility. They are quite stable in acid solution (pH1) and less stable at physiological pH. In human serum, these compounds are immediately metabolized by esterases, producing a mixture of ASA, salicylic acid (SA), and of the related NO-donor benzoic acids, along with other minor products. Due to ASA release, the prodrugs are capable of inhibiting collagen-induced platelet aggregation of human platelet-rich plasma. Simple NO-donor benzoic acids 3-hydroxy-4-(3-nitrooxypropoxy)benzoic acid (28) and 3-(morpholin-4-ylmethyl)-4-[3-(nitrooxy)propoxy]benzoic acid (48) were also studied as representative models of the whole class of benzoic acids formed following metabolism of the prodrugs in serum. These simplified derivatives did not trigger antiaggregatory activity when tested at 300μM. Only 28 displays quite potent NO-dependent vasodilatatory action. Further in vivo evaluation of two selected prodrugs, {[2-(acetyloxy)benzoyl]oxy}methyl-3-[(3-[aminopropanoyl)oxy]-4-[3-(nitrooxy)propoxy]benzoate{dot operator}HCl (38) and {[2-(acetyloxy)benzoyl]oxy}methyl 3-(morpholin-4-ylmethyl)-4-[3-(nitrooxy)propoxy]benzoate oxalate (49), revealed that their anti-inflammatory activities are similar to that of ASA when tested in the carrageenan-induced paw edema assay in rats. The gastrotoxicity of the two prodrugs was also determined to be lower than that of ASA in a lesion model in rats. Taken together, these results indicated that these NO-donor ASA prodrugs warrant further investigation for clinical application.

Chiral pool based efficient synthesis of the aminocyclitol core and furanoside of (-)- hygromycin A: Formal total synthesis of (-)-hygromycin A

A chiral pool based synthetic strategy that leads from the readily available and inexpensive C2-symmetric tartaric acids to the chiral O-isopropylidenebenzooxazolei- a convenient precursor to the aminocyclitol core of hygromycin A as well as the chiral γ-disilyloxybutyrolactone-a pivotal intermediate to approach to the furanoside of hygromycin A.

Studies on synthesis and structure-activity relationship (SAR) of derivatives of a new natural product from marine fungi as inhibitors of influenza virus neuraminidase

Based on the natural isoprenyl phenyl ether from a mangrove-derived fungus, 32 analogues were synthesized and evaluated for inhibitory activity against influenza H1N1 neuraminidase. Compound 15 (3-(allyloxy)-4-hydroxybenzaldehyde) exhibited the most potent inhibitory activity, with IC50 values of 26.96 μM for A/GuangdongSB/01/2009 (H1N1), 27.73 μM for A/Guangdong/03/2009 (H1N1), and 25.13 μM for A/Guangdong/05/2009 (H1N1), respectively, which is stronger than the benzoic acid derivatives (～mM level). These are a new kind of non-nitrogenous aromatic ether Neuraminidase (NA) inhibitors. Their structures are simple and the synthesis routes are not complex. The structure-activity relationship (SAR) analysis revealed that the aryl aldehyde and unsubstituted hydroxyl were important to NA inhibitory activities. Molecular docking studies were carried out to explain the SAR of the compounds, and provided valuable information for further structure modification.