KMS@SIMM
[1,5]-Hydride Shift-Cyclization versus C(sp(2))-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4-and 1,5-Benzoxazepines
Vargane, Dora Szaloki1,2; Toth, Laszlo1,3; Buglyo, Balazs1; Kiss-Szikszai, Attila1; Mandi, Attila1; Matyus, Peter4; Antus, Sandor1; Chen, Yinghan5; Li, Dehai5; Tao, Lingxue6; Zhang, Haiyan6; Kurtan, Tibor1
通讯作者Antus, Sandor(antus.sandor@science.unideb.hu) ; Kurtan, Tibor(kurtan.tibor@science.unideb.hu)
2020-03-02
发表期刊MOLECULES (IF:3.098[JCR-2017],3.268[5-Year])
卷号25期号:6页码:19
摘要Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp(2))-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp(3))-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp(2))-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative had a 6.98 mu M IC50 value.
关键词domino Knoevenagel-[1 5]-hydride shift-cyclization 1 4-benzoxazepine 1 5-benzoxazepine TDDFT-ECD calculation acetylcholinesterase inhibitory activity
WOS关键词C-H BONDS ; CATALYTIC FUNCTIONALIZATION ; BECKMANN REARRANGEMENT ; ASYMMETRIC-SYNTHESIS ; HYDRIDE TRANSFER ; INHIBITORS ; ANALOGS ; ACID ; RING ; DERIVATIVES
DOI10.3390/molecules25061265
收录类别SCI
语种英语
资助项目National Research Development and Innovation Office[K-112951] ; National Research Development and Innovation Office[K-120181] ; EU - European Regional Development Fund[GINOP-2.3.2-15-2016-00008] ; Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences[UNKP-19-4] ; New National Excellence Program of the Ministry for Innovation and Technology
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
WOS类目Biochemistry & Molecular Biology ; Chemistry, Multidisciplinary
WOS记录号WOS:000530248700008
出版者MDPI
引用统计
被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://119.78.100.183/handle/2S10ELR8/280181
专题中国科学院上海药物研究所
通讯作者Antus, Sandor; Kurtan, Tibor
作者单位1.Univ Debrecen, Dept Organ Chem, POB 400, Debrecen 4002, Hungary
2.Univ Debrecen, Doctoral Sch Chem, Egyet Ter 1, Debrecen 4032, Hungary
3.Semmelweis Univ, Dept Organ Chem, Budapest 1094, Hungary
4.Semmelweis Univ, Fac Hlth & Publ Serv, Inst Digital Hlth Sci, Ferenc Ter 15, Budapest 1094, Hungary
5.Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, Qingdao 266003, Peoples R China
6.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zu Chong Zhi Rd,Zhang Jiang Hitech Pk, Shanghai 201203, Peoples R China
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Vargane, Dora Szaloki,Toth, Laszlo,Buglyo, Balazs,et al. [1,5]-Hydride Shift-Cyclization versus C(sp(2))-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4-and 1,5-Benzoxazepines[J]. MOLECULES,2020,25(6):19.
APA Vargane, Dora Szaloki.,Toth, Laszlo.,Buglyo, Balazs.,Kiss-Szikszai, Attila.,Mandi, Attila.,...&Kurtan, Tibor.(2020).[1,5]-Hydride Shift-Cyclization versus C(sp(2))-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4-and 1,5-Benzoxazepines.MOLECULES,25(6),19.
MLA Vargane, Dora Szaloki,et al."[1,5]-Hydride Shift-Cyclization versus C(sp(2))-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4-and 1,5-Benzoxazepines".MOLECULES 25.6(2020):19.
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