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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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.


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Keywords


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

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DOI: 10.5155/eurjchem.13.3.293-298.2266

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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.

References


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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. 3 Dec. 2022
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)

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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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