149428-74-0Relevant articles and documents
Selective cleavage of aryl ether bonds in dimeric lignin model compounds
Zhu, Guodian,Ouyang, Xinping,Yang, Yun,Ruan, Tao,Qiu, Xueqing
, p. 17880 - 17887 (2016/02/27)
Lignin is an abundant renewable feedstock with a complicated and ill-defined structure. As β-O-4 aryl ether bonds are dominant among all the linkages in lignin, it is important to explore lignin depolymerization targeting the cleavage of the β-O-4 aryl ether bond for efficiently utilizing this biomass. Selective cleavage of chemical bonds in β-O-4 lignin model compounds was investigated by using Fe2(SO4)3, HZSM-5 and Pd/C as catalysts under microwave irradiation. When Fe2(SO4)3 or HZSM-5 was used as a catalyst, the Cα-Cβ bond of the C3 side chain in the model compound was broken to form aldehyde, secondary alcohol or ketone compounds. When Pd/C and formate were used as the catalyst, the β-O-4 aryl bond of the non-phenolic model compound was selectively cleaved and hydrogenation of C=C on the side chain occurred at the same time. However, the hydrogenation reaction of C=C on the side chain was faster than that of cleavage of the ether bond. Increasing Pd content favored the selective cleavage of the β-O-4 bond, and microwave irradiation accelerated the cleavage of the β-O-4 bond dramatically. At a high dosage of formate or high temperature, the condensation reaction among phenolic products was promoted due to the presence of an active phenolic hydroxyl group. The β-O-4 bond of the phenolic model compound was also selectively cleaved with Pd/C as the catalyst, and the reaction temperatures of cleaving about one half β-O-4 bonds of the non-phenolic and phenolic model compounds were 120 and 100°C, respectively.
Design, synthesis, structure-activity relationships, and biological characterization of novel arylalkoxyphenylalkylamine σ ligands as potential antipsychotic drugs
Nakazato, Atsuro,Ohta, Kohmei,Sekiguchi, Yoshinori,Okuyama, Shigeru,Chaki, Shigeyuki,Kawashima, Yutaka,Hatayama, Katsuo
, p. 1076 - 1087 (2007/10/03)
Receptor antagonists may be effective antipsychotic drugs that do not induce motor side effects caused by ingestion of classical drugs such as haloperidol. We obtained evidence that 1-(2-dipropylaminoethyl)-4-methoxy- 6H-dibenzo[b,d]pyran hydrochloride 2a had selective affinity for σ receptor over dopamine D2 receptor. This compound was designed to eliminate two bonds of apomorphine 1 to produce structural flexibility for the nitrogen atom and to bridge two benzene rings with a -CH2O- bond to maintain the planar structure. In light of the evidence, N,Y-dipropyl-2-(4-methoxy-3- benzyloxylphenyl)ethylamine hydrochloride 10b was designed. Since compound 10b had eliminated a biphenyl bond of 6H-dibenzo[b,d]pyran derivative 2a, it might be more released from the rigid structure of apomorphine 1 than compound 2a. The chemical modification of compound 10b led to the discovery that N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxyl)phenyl]ethylamine hydrochloride 10g (NE- 100), the best compound among arylalkoxyphenylalkylamine derivatives 3, had a high and selective affinity for σ receptor and had a potent activity in an animal model when the drug was given orally. We report here the design, synthesis, structure-activity relationships, and biological characterization of novel arylalkoxyphenylalkylamine derivatives 3.
