71186-59-9

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 106-95-6 allyl bromide 
• 1048108-36-6 (2-(allyloxy)-5-methoxyphenyl)methanol 
• 4392-24-9 Cinnamyl bromide 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 181280-13-7 2-Allyloxy-5-methoxy-benzaldehyde oxime 
• 354762-26-8 5-(2-allyloxy-5-methoxybezylidene)-1,3-dimethylpyrimidine-2,4,6-(1H,3H,5H)-trione 
• 934569-92-3 1-(2-allyloxy-5-methoxyphenyl)-3-phenylprop-2-yn-1-ol 
• 934569-91-2 1-(2-allyloxy-5-methoxyphenyl)hept-2-yn-1-ol 
• 1048108-36-6 (2-(allyloxy)-5-methoxyphenyl)methanol 
• 1358108-26-5 C₁₈H₁₉NO₃ 
• 1358108-17-4 C₁₈H₁₉NO₃ 
• 1332501-13-9 C₁₈H₁₉NO₃ 
• 1615224-41-3 C₂₈H₃₅BF₂N₄O₄ 
• 1615224-44-6 C₂₇H₃₁BF₂N₄O₄ 
• 1615224-38-8 C₃₁H₃₉BF₂N₄O₄ 

Relevant academic research and scientific papers

Discovery of seneciobipyrrolidine derivatives for the amelioration of glucose homeostasis disorders through 4E-BP1/Akt/AMPK signaling activation

Modulating the glucose transport in skeletal muscle is a promising strategy for ameliorating glucose homeostasis disorders. However, the complicated mechanisms of glucose transport make it difficult to find compounds therapeutically relevant molecular mechanisms of action, while phenotypic screening is thought to be an alternative approach to mimic the cell state of interest. Here, we report (±)-seneciobipyrrolidine (1a) is first found to enhance glucose uptake in L6 myotubes through phenotype-based screening. Further SAR investigation led to the identfication of compound A27 (EC50 = 2.7 μM). Proteomiic analysis discloses the unique function mechanism of A27 through upregulating the level of the eukaryotic translation initiation factor 4E-binding protein 1 (4E-BP1), subsequently enhancing the Akt and AMPK phosphorylation, thereby promoting the glucose uptake. Chronic oral administration of A27 significantly lowers blood glucose and improves glucose tolerance in db/db mice. This work is new research on seneciobipyrrolidine derivatives, providing a promising avenue for ameliorating glucose homeostasis.

Visible-Light-Promoted Cascade Radical Cyclization: Synthesis of 1,4-Diketones Containing Chroman-4-One Skeletons

A visible-light-induced cascade radical cyclization of aroyl chlorides with 2-(allyloxy)-benzaldehyde derivatives has been developed. The method takes advantages of unactivated C=C bonds as the acyl radical acceptors and offers a mild and green approach for the synthesis of 1,4-diketones bearing biologically important chroman-4-one skeletons with moderate to good yields.

Rim-Differentiated C5-Symmetric Tiara-Pillar[5]arenes

The synthesis of "rim-differentiated" C5-symmetric pillar[5]arenes, whose two rims are decorated with different chemical functionalities, has remained a challenging task. This is due to the inherent statistical nature of the cyclization of 1,4-

Synthesis of o-Allyloxy(ethynyl)benzene Derivatives by Cu-Catalyzed Suzuki–Miyaura-Type Reaction and Their Transformations into Heterocyclic Compounds

We have found that Suzuki–Miyaura-type reactions of o-allyloxy(bromoethynyl)benzenes with arylboronic acids using a hydrazone/Cu catalyst system proceeded smoothly in iPrOH under mild conditions to afford the corresponding o-allyloxy(arylethynyl)benzene derivatives in good yields without decomposition of the allyloxy group. We have further demonstrated that annulation and enyne metathesis of the o-allyloxy(arylethynyl)benzene derivatives using transition-metal catalysts led to various heterocyclic compounds.

Cycloisomerization between Aryl Enol Ether and Silylalkynes under Ruthenium Hydride Catalysis: Synthesis of 2,3-Disubstituted Benzofurans

Metal-catalyzed cycloisomerization reactions of 1,n-enynes have become conceptually and chemically attractive processes in the search for atom economy, which is a key subject of current research. However, metal-catalyzed cycloisomerization between aryl enol ether and silylalkynes has not been developed. The ruthenium hydride complex catalyzed cycloisomerization between aryl enol ether and silylalkynes is reported to give benzofurans having useful functional groups, vinyl and trimethylsilylmethyl, on the 2- and 3-positions, respectively.

The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis

The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.

Silaborative Carbocyclizations of 1,7-Enynes. Diastereoselective Preparation of Chromane Derivatives

Palladium(0)-catalyzed carbocyclization of 1,7-enynes mediated by (chlorodimethylsilyl)pinacolborane proceeds with 1,8-addition of the silicon and boron functions to give functionalized cyclohexane derivatives with boron attached to the exocyclic olefin. A variety of chromane dervatives are accessible by this method. In contrast to the analogous reactions with 1,6-enynes, the configuration of the newly formed stereogenic center is controlled by a stereogenic center present in the substrate.

One-pot synthesis of 5-amino-2,5-dihydro-1-benzoxepines: Access to pharmacologically active heterocyclic scaffolds

A one-pot multibond-forming process involving a thermally mediated Overman rearrangement and a ring closing metathesis reaction of allylic trichloroacetimidates bearing a 2-allyloxyaryl group has been developed for the synthesis of 5-amino-substituted 2,5-dihydro-1-benzoxepines. Chemoselective reduction and functionalization of these compounds allowed access to a range of pharmacologically active 5-amino-2,3,4,5-tetrahydro-1-benzoxepine scaffolds.

Design, synthesis and decoration of molecular scaffolds for exploitation in the production of alkaloid-like libraries

The design, synthesis and decoration of six small molecule libraries is described. Each library was inspired by structures embedded in the framework of specific alkaloid natural products. The development of optimised syntheses of the required molecular scaffolds is described, in which reactions including Pd-catalysed aminoarylation and diplolar cycloadditions have been exploited as key steps. The synthesis of selected exemplar screening compounds is also described. In five cases, libraries were subsequently nominated for production on the basis of the scope and limitations of the validation work, as well as predicted molecular properties. In total, the research has led to the successful synthesis of >2500 novel alkaloid-like compounds for addition to the screening collection (the Joint European Compound Library, JECL) of the European Lead Factory.

HKOCl-2 series of green BODIPY-based fluorescent probes for hypochlorous acid detection and imaging in live cells

A HKOCl-2 series of new fluorescent probes for hypochlorous acid (HOCl) detection in live cells is reported. The probes exhibit excellent selectivity, sensitivity, and chemostability toward HOCl. In particular, HKOCl-2b rapidly and selectively detects endogenous HOCl in both human and mouse macrophages. These probes could therefore serve as promising discovery tools to help elucidate biological functions of HOCl.