Synthesis, anti-leishmanial and molecular docking study of bis-indole derivatives

Muhammad Taha,Fazal Rahim,Mohammed A Alqahtani,Mohammed Gollapalli,Rai Khalid Farooq,Noor Barak Almandil,Yasser A Bamarouf,Muhammad Nawaz,Imad Uddin,Mohamed Ibrahim,Manikandan Selvaraj

doi:10.1186/s13065-019-0617-4

Muhammad Taha, Fazal Rahim + Show 9 more

Open Access

https://doi.org/10.1186/s13065-019-0617-4

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Abstract

We have synthesized new series of bisindole analogs (1–27), characterized by 1HNMR and HR-EI-MS and evaluated for their anti-leishmanial potential. All compounds showed outstanding inhibitory potential with IC50 values ranging from 0.7 ± 0.01 to 13.30 ± 0.50 µM respectively when compared with standard pentamidine with IC50 value of 7.20 ± 0.20 µM. All analogs showed greater potential than standard except 10, 19 and 23 when compared with standard. Structure activity relationship has been also established for all compounds. Molecular docking studies were carried out to understand the binding interaction of active molecules.

Highlights

Leishmaniasis has affected almost 98 countries of the world
Structures of all synthesized analogs were confirmed with proton nuclear magnetic resonance (1HNMR), 13carbon nuclear magnetic resonance (13CNMR) and high-resolution electron ionization mass spectrometry (HR-electron impact mass spectra (EIMS)) (Scheme 1)
It was concluded from this study that a series of bisindole analogs (1–27) were synthesized, characterized by 1HNMR and HR-EI-MS and evaluated for their anti-leishmanial potential

Summary

Introduction

Leishmaniasis has affected almost 98 countries of the world. Every year approximately in 2 million people leishmaniasis has been reported while 350 million people are at risk [1]. The first-line drugs used for the treatment of leishmaniasis are pentavalent antimonial compounds which is not too much effective in almost 60% cases due to drug resistance. Some other treatment has been introduced for visceral leishmaniasis which has serious limitation [3]. Some vaccine has been introduced for leishmaniasis infections which are effective with low Bisindole compounds are known to have wide range of pharmacological activities like anticancer and antimicrobial [9,10,11,12,13,14], etc. Amongst several antileishmanial scaffolds reported, indole alkaloids [20,21,22,23,24,25] showed promising activity against Leishmania parasite

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