TFA Mediated Ring-Opening for Evodiamine to Prepare Novel Tryptamine Derivatives | [Journal of Chemical Society of Pakistan • 2024]

Author(s):

1. Hongzhuo Wei: School of Pharmacy, Zunyi Medical University, No.6 Xue Fu West Road, Xin Pu New District, Zunyi City, 563003, Guizhou Province, China.

2. XH Wang: School of Pharmacy, Zunyi Medical University, No.6 Xue Fu West Road, Xin Pu New District, Zunyi City, 563003, Guizhou Province, China.

3. Weihang Guo: School of Pharmacy, Zunyi Medical University, No.6 Xue Fu West Road, Xin Pu New District, Zunyi City, 563003, Guizhou Province, China.

4. Y. H Wang: Department of Pharmacy, Zunyi Medical University Affiliated Hospital, 139 Dalian Road, Zunyi, China

5. C. K. Zhao: School of Pharmacy, Zunyi Medical University, No.6 Xue Fu West Road, Xin Pu New District, Zunyi City, 563003, Guizhou Province, China.

Abstract:

Summary: A convenient feasible protocol was developed for the preparation of novel tryptamine derivatives from evodiamine. After the general alkylation in N-13 and followed by the treatment of TFA in chloroform, a series of tryptamine derivatives 4a-i were successfully synthesized in a good yield, which were immediately cyclized to form alcohol 5 in the condition of NaOH/methanol.

Page(s): 70-80

DOI: 10.52568/001429/JCSP

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 46, Issue: 1, Year: 2024

Keywords:

Alkylation , Tryptamine , Hydrolysis , Evodiamine , Ringopening

References:

[1] der Pharma ,Wang G. Y.,Ma X. Y.,Chin J. .2019 .Discovery of tryptamine derivatives from Bacillus sp. , 28(527) : .

[2] Med ,(2019) M. Khan ,K. M. Khan S.,Parveen S. . .. , 29 : 1133.

[3] Golojuch S.,Kopcial M.,Strzelecka D.,(2020) J. X. Jiang H.,Hu Z. Y.,Li Z. Y.,Fan X.,Li J.,Deng X. .2020 .Design, synthesis and bioactivity study of N-salicyloyl tryptamine derivatives as multifunctional agents for the treatment of neuroinflammation. Eur. J. med., 47(2338) : 115523.

[4] (2020) G. Jaime Q. Jairo I. Braulio,(2014) E. K. Davison M. A.,Brimble M. A.,Zhao Z. L.,Li D. H.,Li D. H. .2015 .Quinolone and indole alkaloids from the fruits of Euodia rutaecarpa and their cytotoxicity against two human cancer cell lines. Phytochemistry, 109(133) : 1998.

[5] (a) G. Z. Huang B.,Kling F. H.,Darras F. H.,Tan J. Q.,Zhang J. Q. .2016 .Its Role in Chronic Diseases, Adv. Exp. Med, 929(315) : .

[6] Wang R.,Deng D.,Shao N. Y. .2018 .Evodiamine activates cellular apoptosis through suppressing PI3K/AKT and activating MAPK in glioma. Oncol. Ther, 11(1183) : .

[7] Guo D. M.,Liu B.,Gao B. .2016 .. Antiproliferative Activity and Cellular Uptake of Evodiamine and Rutaecarpine Based on 3D Tumor Models. Molecules, 21(954) : .

[8] Wen B.,Roongta V.,Liu L. .2014 .Metabolic activation of the indoloquinazoline alkaloids evodiamine and rutaecarpine by human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4, Drug metab. Dispos.: Biol. Fate. Chem, 42(1044) : .

[9] Guo W. H.,Wang X. H.,Zhang J. D. .2021 .Synthesis of ring opening of evodiamine derivatives and evaluation on their biological activity. Chem. Biol. Drug Des, 99(535) : .

Citations

Downloads

Views