Click chemistry inspired synthesis of andrographolide triazolyl conjugates for effective fluorescent sensing of ferric ions. Issue 21 (1st November 2022)

• Record Type: Journal Article
• Authors: Pandey, Nishant; Jyoti, ; Singh, Mangat; Dwivedi, Pratibha; Sahoo, Subash C.; Mishra, Bhuwan B.
• Is Part Of: Natural product research. Volume 36:Issue 21(2022)
• Page Start: 5438
• Page End: 5448
• Publication Date: 2022-11-01
• Subjects: Andrographolide -- triazolyl conjugates -- chemosensor -- ferric ion; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2021.2013837
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: The naturally occurring compound andrographolide 1 was used as a substrate for the synthesis of a novel terminal alkyne 3 which on copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction with azides 4a-l, 7 and 9 furnished a series of regioselective andrographolide triazolyl conjugates 5a-l, 8 and 10, respectively. A free glycoconjugate 6 was also prepared by selective deprotection of compound 5i in good yield. All the compounds were characterized by absorbance, FT-IR, NMR, and HR-MS analyses. The triazolyl conjugate 8 was further investigated as a probe for selective detection of Fe 3+ ion in matrix. The mode of attachment of Fe 3+ ion to the compound 8 was established by absorbance, fluorescence, infrared (IR), and nuclear magnetic resonance (NMR) spectroscopy, and high resolution mass-spectrometry (HR-MS). The logic gate circuits were constructed for the probe 8 and ethylenediaminetetraacetic acid (EDTA). The environmental perspective of probe 8 was investigated in real water samples. Graphical Abstract: UF0001