European Journal of Chemistry 2022, 13(3), 293-298 | doi: https://doi.org/10.5155/eurjchem.13.3.293-298.2266 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Munisaa Younus (1) orcid , Marium Ahsan (2) orcid , Noor-ul Huda (3) orcid , Maria Aqeel Khan (4,*) orcid , Saima Rasheed (5) orcid , Rabia Sadiq (6) orcid , Fatima Zehra Basha (7) orcid

(1) 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
(2) 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
(3) Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(4) 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
(5) Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(6) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(7) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(*) Corresponding Author

Received: 10 Mar 2022 | Revised: 17 Jun 2022 | Accepted: 23 Jun 2022 | Published: 30 Sep 2022 | Issue Date: September 2022

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.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).


Editor-in-Chief
European Journal of Chemistry

Keywords


Diastereomers; Thermal conditions; Biological activities; Indolenine skeleton; Fischer indolization; 2,3,4,4a-Tetrahydro-1H-carbazoles

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.13.3.293-298.2266

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 377 times | icon graph PDF Article downloaded 162 times

Funding information


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.

Citations

/


[1]. Munisaa Younus, Maria Aqeel Khan, Syed Tarique Moin, Fatima Zehra Basha
Engaging Diastereomeric syn‐ and anti‐6‐Bromo‐4a‐isopropyl‐2‐methyl‐2,3,4,4a‐tetrahydro‐1H‐carbazoles in Suzuki Coupling Reaction: Synthesis, Spectral Characterization and DFT Studies
ChemistrySelect  8(23), , 2023
DOI: 10.1002/slct.202300649
/


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


How to cite


Younus, M.; Ahsan, M.; Huda, N.; Khan, M.; Rasheed, S.; Sadiq, R.; Basha, F. Eur. J. Chem. 2022, 13(3), 293-298. doi:10.5155/eurjchem.13.3.293-298.2266
Younus, M.; Ahsan, M.; Huda, N.; Khan, M.; Rasheed, S.; Sadiq, R.; Basha, F. 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(3), 293-298. doi:10.5155/eurjchem.13.3.293-298.2266
Younus, M., Ahsan, M., Huda, N., Khan, M., Rasheed, S., Sadiq, R., & Basha, F. (2022). 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. European Journal of Chemistry, 13(3), 293-298. doi:10.5155/eurjchem.13.3.293-298.2266
Younus, Munisaa, Marium Ahsan, Noor-ul Huda, Maria Aqeel Khan, Saima Rasheed, Rabia Sadiq, & Fatima Zehra Basha. "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." European Journal of Chemistry [Online], 13.3 (2022): 293-298. Web. 27 Sep. 2023
Younus, Munisaa, Ahsan, Marium, Huda, Noor-ul, Khan, Maria, Rasheed, Saima, Sadiq, Rabia, AND Basha, Fatima. "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" European Journal of Chemistry [Online], Volume 13 Number 3 (30 September 2022)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.13.3.293-298.2266


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2022, 13(3), 293-298 | doi: https://doi.org/10.5155/eurjchem.13.3.293-298.2266 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c) 2022 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).



© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.