71186-58-8Relevant articles and documents
Discovery of seneciobipyrrolidine derivatives for the amelioration of glucose homeostasis disorders through 4E-BP1/Akt/AMPK signaling activation
Che, Jinxin,Ma, Canliang,Lu, Jialiang,Chen, Binhui,Shi, Qiuqiu,Jin, Xinxin,Song, Rui,Xu, Fan,Gan, Lishe,Li, Jingya,Hu, Yongzhou,Dong, Xiaowu
, (2021/11/16)
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.
Use of o-hydroxy-p-methoxybenzaldehyde derivative as herbicide
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Paragraph 0008; 0013; 0043; 0049-0050, (2021/04/10)
The invention discloses an application of an o-hydroxy p-methoxybenzaldehyde derivative as a herbicide. The o-hydroxy-p-methoxybenzaldehyde derivative and the herbicide taking the o-hydroxy-p-methoxybenzaldehyde derivative as a component are used for preventing and removing weeds in a field crop growth place and a non-farming crop place.
Synthesis of pterocarpans through palladium-catalyzed oxyarylation of alkoxy-2H-chromenes with o-iodophenols
Gaspar, Francisco V.,Barcellos, Julio C.F.,Cívicos, José F.,Merino, Pedro,Nájera, Carmen,Costa, Paulo R.R.
, (2020/10/22)
The oxyarylation of alkoxy-2H-chromenes (1a-e) with o-iodophenols substituted by electron-withdrawing (CHO) and electron-donating (OMe) groups is studied under two experimental conditions: a) Pd(OAc)2, Ag2CO3 in PEG-400 at 140 °C, 10 min and b) oxime-based palladacycle, DIPEA, in PEG-400 at 150 °C, 3–4 h. Pterocarpans are obtained in moderate to good chemical yields.
Synthesis of chroman-4-one and indanone derivatives via silver catalyzed radical ring opening/coupling/cyclization cascade
Liu, Qiang,Xie, Guanqun,Wang, Qiang,Mo, Zhendong,Li, Chen,Ding, Shujiang,Wang, Xiaoxia
, (2019/09/10)
A variety of chroman-4-one and indanone derivatives were conveniently synthesized from readily available cyclopropanols and alkenyl aldehydes via a silver catalyzed radical ring-opening/coupling/cyclization cascade. The reaction proceeded under mild and neutral conditions with broad substrate scope and afforded the desired products in moderate to good yields. A probable mechanism for the cascade reaction was also proposed.
Regioselective Synthesis of Heteroatom-Functionalized Cyclobutene-triflones and Cyclobutenones
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos
supporting information, p. 2630 - 2639 (2017/08/16)
The controlled metal-free synthesis of a vast variety of heteroatom-containing cyclobutene-triflones [bis(trifluoromethylsulfonyl)cyclobutenes] and cyclobutenones has been developed starting from heteroatom-substituted alkynes and a pyridinium salt (a latent Tf2C=CH2 source). This powerful methodology, involving cyclization reactions, allows for the selective preparation of oxygen-, nitrogen-, bromine-, chlorine-, iodine-, sulfur-, selenium-, tellurium-, phosphorus-, and silicon-functionalized cyclobutene derivatives. (Figure presented.).
Cycloisomerization between Aryl Enol Ether and Silylalkynes under Ruthenium Hydride Catalysis: Synthesis of 2,3-Disubstituted Benzofurans
Ohno, Shohei,Takamoto, Kohei,Fujioka, Hiromichi,Arisawa, Mitsuhiro
supporting information, p. 2422 - 2425 (2017/05/12)
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.
Aldehydes as Carbon Radical Acceptors: Silver Nitrate Catalyzed Cascade Decarboxylation and Oxidative Cyclization toward Dihydroflavonoid Derivatives
Yang, Wen-Chao,Dai, Peng,Luo, Kai,Ji, Yi-Gang,Wu, Lei
supporting information, p. 2390 - 2395 (2017/07/22)
Silver nitrate-catalyzed cascade decarboxylation and oxidative cyclization of α-oxocarboxylic acids, alkenes, and aldehydes is demonstrated for the first time. With ammonium persulfate as the oxidant, the cascade reactions afford dihydroflavonoid derivatives as products in moderate to good yields, exhibiting a broad substrate tolerance. Control experiments indicated that the mechanism includes a radical pathway with aldehydes as the carbon radical acceptors. (Figure presented.).
A conceptually novel construction of the 6a-hydroxypterocarpan skeleton – Synthesis of (±)-variabilin
Ciesielski, Philipp,Metz, Peter
supporting information, p. 6175 - 6177 (2017/09/30)
A new access to the 6a-hydroxypterocarpan variabilin was established. Key step of this concise total synthesis is a challenging cyclization of a haloketone via halogen–metal exchange and subsequent intramolecular addition to the carbonyl function.
Catalytic Intramolecular Cycloaddition Reactions by Using a Discrete Molecular Architecture
Roy, Bijan,Devaraj, Anthonisamy,Saha, Rupak,Jharimune, Suprita,Chi, Ki-Whan,Mukherjee, Partha Sarathi
, p. 15704 - 15712 (2017/10/23)
A discrete tetragonal tube-shaped complex (MT-1) has been synthesised by coordination-driven self-assembly of a carbazole-based tetraimidazole donor L and a Pd(II) 90° acceptor, that is, [cis-(dppf)Pd(OTf)2] (dppf=diphenylphosphinoferrocene, OTf=CF3SO3?). Complex MT-1 was characterised by multinuclear NMR, ESI-MS and single-crystal X-ray diffraction analysis (SCXRD), which showed its symmetrical tetrafacial tube-shaped architecture possessing a large cavity described by four aromatic walls. This coordination cage was successfully utilised as a molecular vessel to perform intramolecular cycloaddition reactions of O-allylated benzylidinebarbituric acid derivatives inside its confined nanospace. The presence of a catalytic amount of MT-1 promoted [4+2] cycloaddition reactions in a regio- and stereoselective manner, yielding the corresponding penta/tetracyclouracil derivatives in good yields under mild reaction conditions. This protocol is interesting compared with the literature reports for the synthesis of similar chromenopyran pyrimidinedione derivatives under high-temperature reflux conditions or solid-state melt reactions (SSMRs).
The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis
Chwastek, Monika,Pieczykolan, Micha?,Stecko, Sebastian
, p. 9046 - 9074 (2016/10/17)
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.
