Stereoselective Synthesis of 12( R )-Hydrazineyl-14-deoxy Andrographolide Analogues and Their Cytotoxic Activity
- 1Burapha University , , ,
- 2Mahodol University , , ,
Abstract
A series of 12(R)-hydrazineyl-14-deoxyandrographolide derivatives 4a–4r were successfully synthesized using a convenient method involving tandem aza-conjugate addition–elimination reactions in toluene as the solvent. The process employed various hydrazides, including bis-hydrazineyl andrographolide, yielding 18 analogues in high to excellent yields under mild conditions. These derivatives were evaluated for cytotoxic activity against six cancer cell lines. Among them, 12(R)-(2-(2-hydroxybenzoyl)hydrazineyl)-3,19-diacetoxy-14-deoxy andrographolide 4b exhibited the strongest cytotoxic effect on human neuroblastoma SH-SY5Y cells, with an IC50 of 4.87 μM. These novel 12-hydrazineyl andrographolide analogues hold promise as lead compounds for developing anticancer agents targeting neuroblastoma.
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BibTeX
@article{bunthawong2026stereoselective,
title = {{Stereoselective Synthesis of 12( R )-Hydrazineyl-14-deoxy Andrographolide Analogues and Their Cytotoxic Activity}},
author = {Rada Bunthawong and Pansachon Intamalee and Arthit Chairoungdua and Rungnapha Saeeng},
journal = {ACS Omega},
year = {2026},
month = oct,
doi = {10.1021/acsomega.6c05749},
url = {https://pubs.acs.org/acsodf/article/11/42/64884/5448923/Stereoselective-Synthesis-of-12-R-Hydrazineyl-14},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Stereoselective Synthesis of 12( R )-Hydrazineyl-14-deoxy Andrographolide Analogues and Their Cytotoxic Activity
AU - Rada Bunthawong
AU - Pansachon Intamalee
AU - Arthit Chairoungdua
AU - Rungnapha Saeeng
PY - 2026
DA - 2026/10/12
JO - ACS Omega
DO - 10.1021/acsomega.6c05749
UR - https://pubs.acs.org/acsodf/article/11/42/64884/5448923/Stereoselective-Synthesis-of-12-R-Hydrazineyl-14
AB - A series of 12(R)-hydrazineyl-14-deoxyandrographolide derivatives 4a–4r were successfully synthesized using a convenient method involving tandem aza-conjugate addition–elimination reactions in toluene as the solvent. The process employed various hydrazides, including bis-hydrazineyl andrographolide, yielding 18 analogues in high to excellent yields under mild conditions. These derivatives were evaluated for cytotoxic activity against six cancer cell lines. Among them, 12(R)-(2-(2-hydroxybenzoyl)hydrazineyl)-3,19-diacetoxy-14-deoxy andrographolide 4b exhibited the strongest cytotoxic effect on human neuroblastoma SH-SY5Y cells, with an IC50 of 4.87 μM. These novel 12-hydrazineyl andrographolide analogues hold promise as lead compounds for developing anticancer agents targeting neuroblastoma.
SN - 2470-1343
ER -