13026-23-8Relevant articles and documents
Intramolecular Electron Transfer and SN2 Reactions in the Radical Anions of 1-(4-Biphenylyl)-ω-haloalkane Studied by Pulse Radiolysis
Kigawa, Hitoshi,Takamuku, Setsuo,Toki, Susumu,Kimura, Norio,Takeda, Seishi,et al.
, p. 5176 - 5179 (1981)
One-electron reduction of 1-(4-biphenylyl)-ω-haloalkane (BPX-n) by solvated electrons and the intramolecular reactions of the radical anion thus formed have been investigated using the pulse-radiolysis technique.The spectrum observed immediately after the pulse has an absorption maximum at 410 nm which is assigned to the corresponding biphenyl radical anion.The decay behavior of all these 410-nm bands follows first-order kinetics and the rates are dependent on the methylene chain length, n.With BPCl-0 and BPCl-2, which provide large rate constants (7.5E7 and 1.7E8 s-1, respectively) and large G values of 4-alkylbiphenyl formation, an intramolecular electron transfer from a biphenyl radical anion to a C-Cl bond is presumed.The rate constants of the radical anions decrease in the order BPCl-1 > BPCl-2 > BPCl-0 which is roughly parallel to the C-Cl bond energy of these compounds and does not correlate with the chain length n, which corresponds to the distance required for the electron transfer.On the other hand, in the case of BPCl-3 and BPCl-4, the decay of the 410-nm band decreased about two orders of magnitude (5.5E5 and 1.2E6 s-1, respectively) and was characterized by a simultanous formation of a 330-nm band which is assigned to a spirocyclic radical.The G values of the corresponding 4-alkylbiphenyl formation were low for these compounds.On the basis of these observations, an intramolecular carbanionic displacement of the biphenyl radical anion on the chlorine center, which is a novel type of intramolecular SN2 reaction, has been concluded.Intramolecular reactions of bromo and iodo derivatives were also investigated and compared with those of corresponding chlorides.
Method for preparing alpha, beta-unsaturated carboxylic acid compound
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Paragraph 0103-0104; 0479-0494, (2021/05/05)
The invention discloses a method for preparing an alpha, beta-unsaturated carboxylic acid compound, which comprises the following steps: 1) in an atmosphere containing carbon dioxide, heating and reacting a mixture containing hydrosilane and a copper catalyst to obtain a system I; and 2) adding a raw material containing alkyne and a nickel catalyst into the system I in the step 1), and heating to react. The method has the advantages of simple, easily available, cheap and stable raw materials, common, easily available and stable catalyst, mild reaction conditions, simple post-treatment, high yield and the like.
The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo
Zhang, Han,Yu, Peilin,Lin, Hongwei,Jin, Zefang,Zhao, Siqi,Zhang, Yi,Xu, Qingxia,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Zhang, Liangren
, p. 3976 - 3996 (2021/05/04)
The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.
