Visiblelight-induced ternary electron donor-acceptor complex enabled synthesis of 2-(2-hydrazinyl) thiazole derivatives and the assessment of their antioxidant and antidiabetic therapeutic potential
A mild and eco-friendly visible-light-induced synthesis of 2-(2-hydrazinyl) thiazole from readily accessible thiosemicarbazide, carbonyl, and phenacyl bromide in the absence of a metal catalyst and/or any extrinsic photosensitizer is reported. This approach only requires a source of visible light an...
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Published in | Organic & biomolecular chemistry Vol. 21; no. 8; pp. 1771 - 1779 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
22.02.2023
Royal Society of Chemistry |
Subjects | |
Online Access | Get full text |
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Summary: | A mild and eco-friendly visible-light-induced synthesis of 2-(2-hydrazinyl) thiazole from readily accessible thiosemicarbazide, carbonyl, and phenacyl bromide in the absence of a metal catalyst and/or any extrinsic photosensitizer is reported. This approach only requires a source of visible light and a green solvent at room temperature to produce the medicinally privileged scaffolds of hydrazinyl-thiazole derivatives in good to outstanding yields. Experimental studies support the
in situ
formation of a visible-light-absorbing, photosensitized colored ternary EDA complex. The next step is to prepare a pair of radicals in an excited state, which makes it easier to prepare thiazole derivatives through a SET and PCET process. DFT calculations additionally supported the mechanistic analysis of the course of the reaction. The antioxidant and antidiabetic properties of some of the compounds in the synthesized library were tested
in vitro
. All the investigated compounds demonstrated appreciable antioxidant activity, as evidenced by the reducing power experiment and the IC
50
values of the DPPH radical scavenging experiment. Furthermore, the IC
50
values for
4c
,
4d
, and
4g
also demonstrated a strong α-amylase inhibitory effect.
A visible-light-induced synthesis of 2-(2-hydrazinyl)thiazole and its antioxidant and antidiabetic therapeutic potential were evaluated. |
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Bibliography: | Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI 2130891-2130893 https://doi.org/10.1039/d2ob02308c ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d2ob02308c |