765312-46-7Relevant academic research and scientific papers
Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf
Zhuang, Daijiao,Gatera, Tharcisse,An, Zhenyu,Yan, Rulong
supporting information, p. 771 - 775 (2022/01/20)
The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes
Design, synthesis and biological evaluation of N-hydroxy-aminobenzyloxyarylamide analogues as novel selective κ opioid receptor antagonists
He, Guangchao,Peng, Kewen,Song, Qiao,Wang, Junwei,Xu, Anhua,Xu, Yungen,Zhu, Qihua
, (2020/05/19)
Aminobenzyloxyarylamide derivatives 1a-i and 2a-t were designed and synthesized as novel selective κ opioid receptor (KOR) antagonists. The benzoyl amide moiety of LY2456302 was changed into N-hydroxybenzamide and benzisoxazole-3(2H)-one to investigate whether it could increase the binding affinity or selectivity for KOR. All target compounds were evaluated in radioligand binding assays for opioid receptor binding affinity. These efforts led to the identification of compound 1c (κ Ki = 179.9 nM), which exhibited high affinity for KOR. Moreover, the selectivity of KOR over MOR and DOR increased nearly 2-fold and 7-fold, respectively, compared with (±)LY2456302.
Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol
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Paragraph 0026; 0027; 0028; 0029; 0082-0085, (2019/05/22)
The invention discloses a method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol. In the atmosphere of inert gas, the amino alcohol and the enol serve as raw materials, potassium tert-butoxide is used as alkali, a series
Design, synthesis and biological evaluation of aminobenzyloxyarylamide derivatives as selective κ opioid receptor antagonists
Wang, Junwei,Song, Qiao,Xu, Anhua,Bao, Yu,Xu, Yungen,Zhu, Qihua
, p. 15 - 25 (2017/03/02)
Opioid receptors play an important role in both behavioral and mood functions. Based on the structural modification of LY2456302, a series of aminobenzyloxyarylamide derivatives were designed and synthesized as κ opioid receptor antagonists. The κ opioid receptor binding ability of these compounds were evaluated with opioid receptors binding assays. Compounds 1a-d showed high affinity for κ opioid receptor. Especially for compound 1c, exhibited a significant Kivalue of 15.7?nM for κ opioid receptor binding and a higher selectivity over μ and δ opioid receptors compared to (±)LY2456302. In addition, compound 1c also showed potent κ antagonist activity with κ IC50?=?9.32?nM in [35S]GTP-γ-S functional assay. The potential use of the representative compounds as antidepressants was also investigated. The most potent compound 1c not only exhibited potent antidepressant activity in the mice forced swimming test, but also displayed the effect of anti-anxiety in the elevated plus-maze test.
Synthesis of 2-arylpyrroles via catalytic dehydrogenation of 2-aryl-1-pyrrolines in the presence of palladium-supported on alumina
Figueira, Cláudia A.,Lopes, Patrícia S.,Gomes, Pedro T.
, p. 4362 - 4371 (2015/06/08)
A convenient synthesis of 2-arylpyrroles from the catalytic dehydrogenation of 2-aryl-1-pyrrolines in the presence of commercial palladium-supported on alumina (Pd/Al2O3) is described. The reaction scope was tested for aryl substituents with different steric hindrances and electronic natures. The dehydrogenation reaction conditions such as temperature, reflux time and amount of catalyst, revealed to be highly dependent on the 2-aryl substituent group, moderate to high yields and selectivities being obtained in a reaction involving straightforward work-up and purification procedures. In addition, the synthesis of the corresponding 2-aryl-1-pyrroline starting materials, through the cyclisation reaction involving 4-chlorobutyronitrile and aryl Grignard reagents, is also reported.
The reaction of cyclic imines with the Ruppert-Prakash reagent. Facile approach to α-trifluoromethylated nornicotine, anabazine, and homoanabazine
Shevchenko, Nikolay E.,Vlasov, Katja,Nenajdenko, Valentine G.,R?schenthaler, Gerd-Volker
scheme or table, p. 69 - 74 (2011/02/27)
We have demonstrated that the Ruppert-Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding α-trifluoromethyl derivatives of nitrogen heterocycles. 5-7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized.
Reactions of cyclopropyl aryl ketones with sulfonamides mediated by Zr(OTf)4: Cascade preparation of 5-aryl-3,4-dihydro-2H-pyrrole
Shi, Min,Yang, Yong-Hua,Xu, Bo
, p. 1622 - 1624 (2007/10/03)
We found that the Lewis acid Zr(OTf)4 can effectively promote the ring-opening reaction of cyclopropyl aryl ketones with sulfonamides. By controlling the reaction conditions, we could obtain the ring-opened products 3 and the cyclized products 5 in moderate to good yields. This process provides a novel and efficient route for the synthesis of 5-aryl-3,4-dihydro-2H-pyrrole in the presence of a Lewis acid.
