Genipin 1, derived from geniposide present in the fruit of Gardenia jasminoides Ellis has been reported to show diverse pharmacological activity. In this work, a new series of genipintriazole analogues was designed and synthesized yielding high yields from naturally genipin and their cytotoxicity evaluated against six cancer cell lines. Twenty-seven analogues were obtained using a convenient four-step reaction methods. Six analogues showed higher cytotoxic activity than the original genipin and benzylether-triazolegenipin 5 j exhibited the strongest activity against P-388 and A-549 cancer cell lines with IC 50 values of 2.54 and 4.53 μM. The structure-activity relationships (SARs) study indicated that the introduction of dibenzyl ether, substituted silyl and long chain aliphatic-triazoles at C-10 position of genipin were most effective in improving cytotoxicity. Molecular docking results provided the information for further modification of genipin scaffold for development as cytotoxic agent.
A novel series of
1,2,3-triazole-genipin analogues were designed,
synthesized, and evaluated for neuroprotective activity, acetylcholinesterase
(AChE), and butyrylcholinesterase (BuChE) inhibitory activity. The
genipin analogues bearing bromoethyl- and diphenylhydroxy-triazole
showed in vitro neuroprotective properties against
H2O2 toxicity along with potent inhibitory activity
on BuChE with IC50 values of 31.77 and 54.33 μM,
respectively, compared with galantamine (IC50 = 34.05 μM).
The molecular docking studies of these genipin analogues showed good
binding energy and interact well with the key amino acids of BuChE via hydrogen-bonding and hydrophobic interactions. Triazole
genipins might be promising lead compounds as anti-Alzheimer’s
agents.
A new hypervalent‐iodine(III)‐mediated tandem reaction involving oxidative dearomatization and in situ aziridination of phenolic amines is described, providing a mild and effective method for the assembly of structurally interesting and synthetically useful aziridines. Importantly, the densely functionalized aziridines resulting from this unprecedented tandem reaction offer a platform for expeditious access to architecturally diverse aza‐heterocycles through transformations initiated by selective ring‐opening of aziridines.
This paper reports the acid-controlled divergent synthesis of 3-pyrrolidin-2-yl-1H-indoles and symmetric and unsymmetrical bis(indolyl)methanes (BIMs) through photocatalyzed decarboxylative coupling and Friedel−Crafts alkylation reactions, respectively. The protocol involves C−H functionalization, switching formation of two products, room-temperature conditions, low photocatalyst loadings, without strong oxidant, and moderate to excellent yields. This method has been applied for the synthesis of natural product vibrindole A and 1,1-bis(1H-indol-3yl)-2-phenylethane.
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