Synthesis of Clausena Alkaloids Using Unique Ring Expansion of Dihydroisoquinolines and Their Cholinesterase Inhibitory Activity

Rattana Worayuthakarn; Chuleeporn Ngernnak; Somsak Ruchirawat; Kittipong Chainok; Nanthawat Wannarit; Nopporn Thasana

doi:10.1055/s-0042-1752658

Synthesis, Table of Contents

Synthesis 2023; 55(14): 2241-2252
DOI: 10.1055/s-0042-1752658

paper

Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

Synthesis of Clausena Alkaloids Using Unique Ring Expansion of Dihydroisoquinolines and Their Cholinesterase Inhibitory Activity

Rattana Worayuthakarn∗

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

,

Chuleeporn Ngernnak

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

,

Somsak Ruchirawat

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^bChemical Sciences Program, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^cCenter of Excellence on Environmental Health and Toxicology (EHT), OPS, Ministry of Higher Education, Science, Research and Innovation, Bangkok 10400, Thailand

,

Kittipong Chainok

^dThammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TUMCMA), Faculty of Science and Technology, Thammasat University, Pathumthani 12121, Thailand

,

Nanthawat Wannarit

^dThammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TUMCMA), Faculty of Science and Technology, Thammasat University, Pathumthani 12121, Thailand

^eDepartment of Chemistry, Faculty of Science and Technology, Thammasat University, Pathumthani 12121, Thailand

,

Nopporn Thasana∗

^aLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^bChemical Sciences Program, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand

^cCenter of Excellence on Environmental Health and Toxicology (EHT), OPS, Ministry of Higher Education, Science, Research and Innovation, Bangkok 10400, Thailand

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Abstract

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Abstract

A facile and direct synthetic entry to the carbon skeleton of Clausena alkaloids, the benzo[d]azocin-4-one, is reported featuring the ring expansion of 1-phenyldihydroisoquinoline derivatives initially triggered by oxazolone under environmentally benign conditions in a one-pot procedure. Functionalization of the eight-membered lactam framework provided a set of Clausena alkaloid derivatives. Some derivatives show a promising inhibition toward acetylcholinesterase and a better selectivity index than the previously used Alzheimer’s disease (AD) drug, tacrine, and the currently used AD drug, galantamine.

Key words

Clausena alkaloids - ζ-clausenamides - balasubramides - benzo[d]azocinones - eight-membered lactams - ring expansion

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References

References

1a Arbab IA, Abdul AB, Aspollah M, Abdullah R, Abdelwahab SI, Mohan S, Abdelmageed AH. A. J. Med. Plants Res. 2011; 5: 7177
1b Huang L, Feng Z.-L, Wang Y.-T, Lin L.-G. Chin. J. Nat. Med. 2017; 15: 881

2 Liu GT, Li W.-X, Chen Y.-Y, Wei H.-L. Drug Dev. Res. 1996; 39: 174

3a Cui C.-B, Yan S.-Y, Cai B, Yao X.-S. J. Asian Nat. Prod. Res. 2002; 4: 233
3b Ito C, Ohta H, Tan HT. W, Furukawa H. Chem. Pharm. Bull. 1996; 44: 2231
3c Kumar V, Reisch J, Wickramasinghe A. Aust. J. Chem. 2008; 42: 1375
3d Sripisut T, Laphookhieo S. J. Asian Nat. Prod. Res. 2010; 12: 614
3e Sunthitikawinsakul A, Kongkathip N, Kongkhathip B, Phonnakhu S, Daly JW, Spande TF, Nimit Y, Rochanaruangrai S. Planta Med. 2003; 69: 155
3f Wu T.-S, Huang S.-C, Lai J.-S, Teng C.-M, Ko F.-N, Kuoh C.-S. Phytochemistry 1993; 32: 449
3g Xin Z.-Q, Lu J.-J, Ke C.-Q, Hu C.-X, Lin L.-P, Ye Y. Chem. Pharm. Bull. 2008; 56: 827
3h Chaichantipyuth C, Pummangura S, Naowsaran K, Thanyavuthi D. J. Nat. Prod. 1988; 51: 1285
3i Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitagawa Y, Tokuda H, Nishino H, Furukawa H. J. Nat. Prod. 2000; 63: 125
3j Maneerat W, Ritthiwigrom T, Cheenpracha S, Promgool T, Yosathera K, Deachathai S, Phakhodee W, Laphookhieo S. J. Nat. Prod. 2012; 75: 741
3k Liu H, Li C.-J, Yang J.-Z, Ning N, Si Y.-K, Li L, Chen N.-H, Zhao Q, Zhang D.-M. J. Nat. Prod. 2012; 75: 677
3l Shen D.-Y, Chan Y.-Y, Hwang T.-L, Juang S.-H, Huang S.-C, Kuo P.-C, Thang TD, Lee E.-J, Damu AG, Wu T.-S. J. Nat. Prod. 2014; 77: 1215
3m Liu Y.-P, Guo J.-M, Liu Y.-Y, Hu S, Yan G, Qiang L, Fu Y.-H. J. Agric. Food Chem. 2019; 67: 5764
3n Liu Y.-P, Guo J.-M, Xie Z, Suo X.-Y, Liu Z.-Y, Qiao Z.-H, Guan R.-Q, Bian Y, Qiang L, Fu Y.-H. J. Org. Chem. 2021; 86: 17722

4 Wu T.-S, Huang S.-C, Wu P.-L. Tetrahedron Lett. 1996; 37: 7819
5 Ngadjui BT, Ayafor JF, Sondengam BL, Connolly JD. Phytochemistry 1989; 28: 1517
6 Lin J.-H. Phytochemistry 1989; 28: 621

7a Yang M.-H, Chen Y.-Y, Huang L. Chin. Chem. Lett. 1991; 2: 291
7b Yang M.-H, Chen Y.-Y, Huang L. Phytochemistry 1988; 27: 445

8 Sun X, Li C, Ma J, Zang Y, Huang J, Chen N, Wang X, Zhang D. Fitoterapia 2021; 154: 104999
9 Riemer B, Hofer O, Greger H. Phytochemistry 1997; 45: 337

10a Yang L, Deng G, Wang D.-X, Huang Z.-T, Zhu J.-P, Wang M.-X. Org. Lett. 2007; 9: 1387
10b Ma N, Wu K, Huang L. Eur. J. Med. Chem. 2008; 43: 893
10c Yang L, Wang D.-X, Zheng Q.-Y, Pan J, Huang Z.-T, Wang M.-X. Org. Biomol. Chem. 2009; 7: 2628
10d Johansen MB, Leduc AB, Kerr MA. Synlett 2007; 2593
10e Li J, Li J, Xu Y, Wang Y, Zhang L, Ding L, Xuan Y, Pang T, Lin H. Nat. Prod. Res. 2016; 30: 800
10f Juárez-Calderón M, Aparicio DM, Gnecco D, Juárez JR, Orea L, Mendoza A, Sartillo-Piscil F, del Olmo E, Terán JL. Tetrahedron Lett. 2013; 54: 2729

11a Worayuthakarn R, Thasana N, Ruchirawat S. Org. Lett. 2006; 8: 5845
11b Boonya-udtayan S, Eno M, Ruchirawat S, Mahidol C, Thasana N. Tetrahedron 2012; 68: 10293

12 Movassaghi M, Hill MD. Org. Lett. 2008; 10: 3485
13 Tabata H, Suzuki H, Akiba K, Takahashi H, Natsugari H. J. Org. Chem. 2010; 75: 5984
14 CCDC 2209415 (16c) and CCDC 2209511 (12) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures. Also see Supporting Information.

15a Szabó T, Papp M, Németh DR, Dancsó A, Volk B, Milen M. J. Org. Chem. 2021; 86: 128
15b Haddach AA, Kelleman A, Deaton-Rewolinski MV. Tetrahedron Lett. 2002; 43: 399

16 Sawettanai N, Leelayuwapan H, Karoonuthaisiri N, Ruchirawat S, Boonyarattanakalin S. J. Org. Chem. 2019; 84: 7606
17 Ellman GL, Courtney KD, Andres V, Featherstone RM. Biochem. Pharmacol. 1961; 7: 88

Supplementary Material

Supporting Information