European Journal of Chemistry

Exploring the diastereoselectivity for Fischer indolization of L-menthone under different conditions, spectral characterization, and biological activities of new (2R,4aS)-2,3,4,4a-tetrahydro-1H-carbazole analogs

Crossmark


Main Article Content

Munisaa Younus
Marium Ahsan
Noor-ul Huda
Maria Aqeel Khan
Saima Rasheed
Rabia Sadiq
Fatima Zehra Basha

Abstract

Tetrahydrocarbazoles are important class of heterocycles that exhibit numerous biological properties. They are also found in several natural products. In the present study, Fischer indolization of L-menthone was investigated for diastereoselectivity using different reaction conditions. No appreciable diastereoselectivity was observed for the acids used except CuBr and boric acid at varying temperatures, where satisfactory results were obtained. In addition, a small library of new (2R,4aS)-2,3,4,4a-tetrahydro-1H-carbazole analogs was reported and structurally characterized using spectroscopic techniques herein. Additionally, the compounds were evaluated against different biological activities, such as carbonic anhydrase inhibitory, immunomodulatory, and anticancer activities and did not show any activity. As the synthesized library was found safe when tested against cytotoxicity in normal cell line, it will be explored for other biological activities in near future to identify its biological outcome.


icon graph This Abstract was viewed 552 times | icon graph Article PDF downloaded 299 times

How to Cite
(1)
Younus, M.; Ahsan, M.; Huda, N.- ul; Khan, M. A.; Rasheed, S.; Sadiq, R.; Basha, F. Z. Exploring the Diastereoselectivity for Fischer Indolization of L-Menthone under Different Conditions, Spectral Characterization, and Biological Activities of New (2R,4aS)-2,3,4,4a-Tetrahydro-1H-Carbazole Analogs. Eur. J. Chem. 2022, 13, 293-298.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Chaudhari, T. Y.; Tandon, V. Recent approaches to the synthesis of tetrahydrocarbazoles. Org. Biomol. Chem. 2021, 19, 1926-1939.
https://doi.org/10.1039/D0OB02274H

[2]. Bublitz, M.; Kjellerup, L.; Cohrt, K. O.; Gordon, S.; Mortensen, A. L.; Clausen, J. D.; Pallin, T. D.; Hansen, J. B.; Fuglsang, A. T.; Dalby-Brown, W.; Winther, A.-M. L. Tetrahydrocarbazoles are a novel class of potent P-type ATPase inhibitors with antifungal activity. PLoS One 2018, 13, e0188620.
https://doi.org/10.1371/journal.pone.0188620

[3]. Ivanenkov, Y. A.; Osterman, I. A.; Komarova, E. S.; Bogdanov, A. A.; Sergiev, P. V.; Dontsova, O. A.; Sofronova, A. A.; Terentiev, V. A.; Filkov, G. I.; Yamidanov, R. S.; Majouga, A. G.; Bezrukov, D. S.; Deyneka, E. V.; Skvortsov, D. A. Tetrahydrocarbazoles as novel class of DNA bio synthesis inhibitors in bacteria. Antiinfect. Agents 2020, 18, 121-127.
https://doi.org/10.2174/2211352517666181218155259

[4]. Gudmundsson, K. S.; Sebahar, P. R.; Richardson, L. D.; Catalano, J. G.; Boggs, S. D.; Spaltenstein, A.; Sethna, P. B.; Brown, K. W.; Harvey, R.; Romines, K. R. Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses. Bioorg. Med. Chem. Lett. 2009, 19, 3489-3492.
https://doi.org/10.1016/j.bmcl.2009.05.003

[5]. Ghobadian, R.; Mahdavi, M.; Nadri, H.; Moradi, A.; Edraki, N.; Akbarzadeh, T.; Sharifzadeh, M.; Bukhari, S. N. A.; Amini, M. Novel tetrahydrocarbazole benzyl pyridine hybrids as potent and selective butryl cholinesterase inhibitors with neuroprotective and β-secretase inhibition activities. Eur. J. Med. Chem.2018, 155, 49-60.
https://doi.org/10.1016/j.ejmech.2018.05.031

[6]. Ha, J. D.; Kang, S. K.; Cheon, H. G.; Choi, J. K. Synthesis of Tetrahydro carbazole Derivatives as Potent β3-Adrenoceptor Agonists. Bull. Korean Chem. Soc.2004, 25, 1784-1790.
https://doi.org/10.5012/bkcs.2004.25.12.1784

[7]. El-Nassan, H. B. Synthesis and antitumor activity of tetrahydro carbazole hybridized with dithioate derivatives. J. Enzyme Inhib. Med. Chem. 2015, 30, 308-315.
https://doi.org/10.3109/14756366.2014.922554

[8]. Amat, M.; Coll, M.-D.; Bosch, J.; Espinosa, E.; Molins, E. Total syntheses of the Strychnos indole alkaloids (−)-tubifoline, (−)-tubifolidine, and (−)-19,20-dihydroakuammicine. Tetrahedron Asymmetry 1997, 8, 935-948.
https://doi.org/10.1016/S0957-4166(97)00071-2

[9]. Gan, P.; Pitzen, J.; Qu, P.; Snyder, S. A. Total synthesis of the caged indole alkaloid arboridinine enabled by aza-Prins and metal-mediated cyclizations. J. Am. Chem. Soc. 2018, 140, 919-925.
https://doi.org/10.1021/jacs.7b07724

[10]. Li, W.; Chen, Z.; Yu, D.; Peng, X.; Wen, G.; Wang, S.; Xue, F.; Liu, X.-Y.; Qin, Y. Asymmetric total syntheses of the akuammiline alkaloids (−)‐strictamine and (−)‐rhazinoline. Angew. Chem. Weinheim Bergstr. Ger. 2019, 131, 6120-6124.
https://doi.org/10.1002/ange.201901074

[11]. Tan, S.-J.; Low, Y.-Y.; Choo, Y.-M.; Abdullah, Z.; Etoh, T.; Hayashi, M.; Komiyama, K.; Kam, T.-S. Strychnan and secoangustilobine A type alkaloids from Alstoniaspatulata. Revision of the C-20 configuration of scholaricine. J. Nat. Prod. 2010, 73, 1891-1897.
https://doi.org/10.1021/np100552b

[12]. Szabó, T.; Volk, B.; Milen, M. Recent advances in the synthesis of β-carboline alkaloids. Molecules 2021, 26, 663.
https://doi.org/10.3390/molecules26030663

[13]. Jin, G.-L.; He, S.-D.; Lin, S.-M.; Hong, L.-M.; Chen, W.-Q.; Xu, Y.; Yang, J.; Li, S.-P.; Yu, C.-X. Koumine attenuates neuroglia activation and inflammatory response to neuropathic pain. Neural Plast. 2018, 2018, 1-13.
https://doi.org/10.1155/2018/9347696

[14]. Khan, M. A.; Fazal-ur-Rehman, S.; Hameed, A.; Kousar, S.; Dalvandi, K.; Yousuf, S.; Choudhary, M. I.; Basha, F. Z. Regioselective synthesis of novel 2,3,4,4a-tetrahydro-1H-carbazoles and their cholinesterase inhibitory activities. RSC Adv. 2015, 5, 59240-59250.
https://doi.org/10.1039/C5RA10461K

[15]. Iqbal, S.; Saleem, M.; Azim, M. K.; Taha, M.; Salar, U.; Khan, K. M.; Perveen, S.; Choudhary, M. I. Carbohydrazones as new class of carbonic anhydrase inhibitors: Synthesis, kinetics, and ligand docking studies. Bioorg. Chem. 2017, 72, 89-101.
https://doi.org/10.1016/j.bioorg.2017.03.014

[16]. Shank, R. P.; Doose, D. R.; Streeter, A. J.; Bialer, M. Plasma and whole blood pharmacokinetics of topiramate: the role of carbonic anhydrase. Epilepsy Res. 2005, 63, 103-112.
https://doi.org/10.1016/j.eplepsyres.2005.01.001

[17]. Iqbal, S.; Khan, M. A.; Ansari, Z.; Jabeen, A.; Faheem, A.; Fazal-Ur-Rehman, S.; Basha, F. Z. Synthesis of new bicarbazole-linked triazoles as non-cytotoxic reactive oxygen species (ROS) inhibitors. Synth. Commun. 2019, 49, 2330-2341.
https://doi.org/10.1080/00397911.2019.1620281

[18]. Farooq, R.; Hussain, N.; Yousuf, S.; Atia-Tul-Wahab; Ahmad, M. S.; Atta-Ur-Rahman; Choudhary, M. I. Microbial transformation of mestanolone by Macrophomina phaseolina and Cunninghamella blakesleeana and anticancer activities of the transformed products. RSC Adv. 2018, 8, 21985-21992.
https://doi.org/10.1039/C8RA01309H

[19]. Batool, F.; Khan, M. A.; Shaikh, N. N.; Iqbal, S.; Akbar, S.; Fazal-ur-rehman, S.; Choudhary, M. I.; Basha, F. Z. New benzamide analogues of metronidazole‐tethered triazoles as non‐sugar-based inhibitors of β‐glucuronidase. ChemistrySelect 2019, 4, 8634-8637.
https://doi.org/10.1002/slct.201901870

Supporting Agencies

Third World Center for Science and Technology, Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan.
Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).