Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2020; 52(11): 1680-1686
DOI: 10.1055/s-0039-1690871
DOI: 10.1055/s-0039-1690871
paper
Palladium-Catalyzed Cascade Synthesis of Novel Quinolone- Bis(indolyl)methane Hybrids as Promising α-Glucosidase Inhibitors
The work was financially supported by NSFC (No. 21762014) and Guizhou Provincial Engineering Research Center for Natural Drugs.Further Information
Publication History
Received: 14 February 2020
Accepted after revision: 10 March 2020
Publication Date:
30 March 2020 (online)

§ These authors contributed equally to this work
Abstract
An unexpected cascade reaction is developed for the construction of functionalized 3-bis(indol-3-yl)methylquinoline-2(1H)-ones. Three C–C bonds and one ring are created in one pot triggered by Pd-catalyzed C-3 alkenylation of indole with 2-acyl-N-acrylaniline derivatives. A series of complex and specific quinoline-2(1H)-ones were produced, most of them showed significant α-glucosidase inhibitory activities.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690871.
- Supporting Information
-
References
- 1a Dhiman P, Arora N, Thanikachalam PV, Monga V. Bioorg. Chem. 2019; 92: 103291
- 1b Chu XM, Wang C, Liu W, Liang LL, Gong KK, Zhao CY, Sun KL. Eur. J. Med. Chem. 2019; 161: 101
- 1c Gao F, Zhang X, Wang TF, Xiao JQ. Eur. J. Med. Chem. 2019; 165: 59
- 2a Tuchinda P, Pohmakotr M, Munyoo B, Reutrakul V, Santisuk T. Phytochemistry 2000; 53: 1079
- 2b Reisch J, Gunaherath GM. K. B. Monatsh. Chem. 1988; 119: 1169
- 3 Praveen PJ, Parameswaran PS, Majik MS. Synthesis 2015; 47: 1827
- 4 Imran S, Taha M, Ismail NH. Curr. Med. Chem. 2015; 22: 4412
- 5a Gong HW, Xie ZF. Chin. J. Org. Chem. 2012; 32: 1195
- 5b Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Chem. Rev. 2010; 110: 2250
- 6 Palmieri A, Petrini M. Synthesis 2019; 51: 829
- 7a Gorsline BJ, Wang L, Ren P, Carrow BP. J. Am. Chem. Soc. 2017; 139: 9605
- 7b Verma AK, Danodia AK, Saunthwa RK, Patel M, Choudhary D. Org. Lett. 2015; 17: 3658
- 7c Laha JK, Dayal N. Org. Lett. 2015; 17: 4742
- 7d Ozaki K, Zhang H, Ito H, Lei AW, Itami K. Chem. Sci. 2013; 4: 3416
- 7e Huang QF, Song QQ, Cai J, Zhang XF, Lin S. Adv. Synth. Catal. 2013; 355: 1512
- 7f Chen WL, Gao YR, Mao S, Zhang YL, Wang YF, Wang YQ. Org. Lett. 2012; 14: 5920
- 7g Grimster NP, Gauntlett C, Godfrey CR. A, Gaunt MJ. Angew. Chem. Int. Ed. 2005; 44: 3125
- 8 Petrini M. Chem. Eur. J. 2017; 23: 16115
- 9 Lin K, Jian Y, Zhao P, Zhao CS, Pan WD, Liu S. Org. Chem. Front. 2018; 5: 590
- 10 Jia CG, Lu WJ, Kitamura T, Fujiwara Y. Org. Lett. 1999; 1: 2097
- 11 Zhao P, Huang ZY, Zhao CS, Liu S. J. Heterocycl. Chem. 2019; 59: 108
- 12 Zhang SC, Chen ZQ, Qin SH, Lou CL, Senan AM, Liao RZ, Yin GC. Org. Biomol. Chem. 2016; 14: 4146
- 13 Kiamehr M, Alipour B, Mohammadkhani L, Jafari B, Langer P. Tetrahedron 2017; 73: 3040