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

doi:10.5155/eurjchem.13.3.293-298.2266

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Published: Sep 30, 2022

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

Keywords:

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

Section

Research Article

Issue

Vol. 13 No. 3 (2022): September 2022

Dates

Received 2022-03-10
Accepted 2022-06-23
Published 2022-09-30

Munisaa Younus

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

https://orcid.org/0000-0001-7297-5526

Marium Ahsan

https://orcid.org/0000-0002-1106-8882

Noor-ul Huda

Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

https://orcid.org/0000-0003-0790-0143

Maria Aqeel Khan

https://orcid.org/0000-0002-8072-4775

Saima Rasheed

Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

https://orcid.org/0000-0002-6742-3003

Rabia Sadiq

Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

https://orcid.org/0000-0003-2493-4898

Fatima Zehra Basha

Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

https://orcid.org/0000-0001-8092-7639

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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(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.

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