Synthesis, anti-plasmodial and cytotoxic evaluation of 1H-1,2,3-triazole/acyl hydrazide integrated tetrahydro-β-carboline-4-aminoquinoline conjugates

Bharvi Sharma; Simranjeet Kaur; Jenny Legac; Philip J Rosenthal; Vipan Kumar

doi:10.1016/j.bmcl.2019.126810

Synthesis, anti-plasmodial and cytotoxic evaluation of 1H-1,2,3-triazole/acyl hydrazide integrated tetrahydro-β-carboline-4-aminoquinoline conjugates

Bioorg Med Chem Lett. 2020 Jan 15;30(2):126810. doi: 10.1016/j.bmcl.2019.126810. Epub 2019 Nov 11.

Authors

Bharvi Sharma¹, Simranjeet Kaur¹, Jenny Legac², Philip J Rosenthal², Vipan Kumar³

Affiliations

¹ Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India.
² Department of Medicine, University of California, San Francisco, CA, USA.
³ Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India. Electronic address: [email protected].

PMID: 31740250
DOI: 10.1016/j.bmcl.2019.126810

Abstract

A series of 1H-1,2,3-triazole/acylhydrazide-tethered tetrahydro-β-carboline-4-aminoquinoline conjugates was synthesized with an aim to study their anti-plasmodial structure-activity relationship. The presence of 1H-1,2,3-triazole-core along with a flexible alkyl chain length on aminoquinoline core has favourable influence on the anti-plasmodial activity against Chloroquine-resistant W2 strain of P. falciparum while the introduction of hydrazine core not only diminished the activities but also resulted in increased cytotoxicity against mammalian Vero cells.

Keywords: Acyl hydrazide; Antiplasmodial; Quinoline; Tetrahydro-β-carboline; Triazole.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aminoquinolines / chemical synthesis*
Humans
Hydrazines / chemical synthesis*
Molecular Structure
Plasmodium falciparum / drug effects
Structure-Activity Relationship

Substances

Aminoquinolines
Hydrazines
hydrazine
4-aminoquinoline