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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)
, Marium Ahsan (2) , Noor-ul Huda (3) , Maria Aqeel Khan (4,*) , Saima Rasheed (5) , Rabia Sadiq (6) , Fatima Zehra Basha (7) (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.
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DOI: 10.5155/eurjchem.13.3.293-298.2266
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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
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DOI Link: https://doi.org/10.5155/eurjchem.13.3.293-298.2266
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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
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