Alpha 2.0
Login Register
» Articles » PMID: 21826182

Novel 5, 6-Dihydropyrrolo[2,1-a]isoquinolines As Scaffolds for Synthesis of Lamellarin Analogues

Overview
Journal Evid Based Complement Alternat Med
Specialty Rehabilitation Medicine
Date 2011 Aug 10
PMID 21826182
Citations 2
Authors
Shao Han Liao
Dai Hua Hu
Ai Ling Wang
De Peng Li
Affiliations
Soon will be listed here.
Abstract

AS CORE SKELETONS OF LAMELLARINS: 5,6-Dihydropyrrolo[2,1-a]isoquinolines are one of the important alkaloids that exhibit significant biological activities, in this study, an efficient synthetic route was described for two novel compounds, 5,6-dihydropyrrolo[2,1-a]isoquinolines I and II. Compound I was synthesized from isovanillin with 28.3% overall yield by a six-step reaction while II from 2-(3, 4-dimethoxyphenyl) ethanamine was with 61.6% overall yield by a three-step reaction. And the structures of these two compounds were confirmed by means of IR spectrum, (1)H NMR, (13)C NMR, MS, HRMS, and melting point measurements.

Citing Articles

Design and Synthesis of Pyrrolo[2,1-a]Isoquinoline-Based Derivatives as New Cytotoxic Agents.

Kakhki S, Shahosseini S, Zarghi A Iran J Pharm Res. 2017; 15(4):743-751.

PMID: 28243270 PMC: 5316252.

Anticancer properties of lamellarins.

Bailly C Mar Drugs. 2015; 13(3):1105-23.

PMID: 25706633 PMC: 4377975. DOI: 10.3390/md13031105.

References
1.
Batra S, Sabnis Y, Rosenthal P, Avery M . Structure-based approach to falcipain-2 inhibitors: synthesis and biological evaluation of 1,6,7-trisubstituted dihydroisoquinolines and isoquinolines. Bioorg Med Chem. 2003; 11(10):2293-9. DOI: 10.1016/s0968-0896(03)00117-2. View
2.
Bermejo A, Andreu I, Suvire F, Leonce S, Caignard D, Renard P . Syntheses and antitumor targeting G1 phase of the cell cycle of benzoyldihydroisoquinolines and related 1-substituted isoquinolines. J Med Chem. 2002; 45(23):5058-68. DOI: 10.1021/jm020831a. View
3.
Cabedo N, Protais P, Cassels B, Cortes D . Synthesis and dopamine receptor selectivity of the benzyltetrahydroisoquinoline, (R)-(+)-nor-roefractine. J Nat Prod. 1998; 61(6):709-12. DOI: 10.1021/np980008a. View
4.
Facompre M, Tardy C, Bal-Mahieu C, Colson P, Perez C, Manzanares I . Lamellarin D: a novel potent inhibitor of topoisomerase I. Cancer Res. 2003; 63(21):7392-9. View
5.
Ploypradith P, Petchmanee T, Sahakitpichan P, Litvinas N, Ruchirawat S . Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings. J Org Chem. 2006; 71(25):9440-8. DOI: 10.1021/jo061810h. View