An efficient green synthesis of 1-amidoalkyl-2-naphthol derivatives 4 a-s has been developed, employing phenylboronic acid, by a three component one-pot condensation reaction of 2naphthol, a wide range of functionalized aromatic aldehydes and acetamide, or acrylamide under solvent-free conditions. This new protocol has the rewards of ecologically benign, easy workup along with good to excellent yields. Moreover, selected compounds were screened towards inhibition of cholinesterase. In vitro studies showed that some synthesized compounds have significant both AChE and BChE inhibitory activities compared to Galanthamine (reference drug). Compounds 4 p and 4 s were the most effective showing high potential AChE and BChE inhibitory activities with respective IC 50 values of 13.81 � 0.54 μM and 31.70 � 1.29 μM. Subsequent evaluation of the α-glucosidase inhibitory activity of the target molecules revealed that compound 4 s with an IC 50 value of 2.05 � 0.05 μM exhibited highest activity. These preliminary results provide promising sources of multifunctional agents and sheds light on their potential usage in medicine and in the pharmaceutical industries. Using molecular docking approach, we tried to get insights into binding interactions of our synthesized compounds to act as AChE and BChE inhibitors and understand the facts that underlie the relationships between structural modifications on these ligands and their efficacy.
This compound crystallizes with two independent molecules (A and B) in the asymmetric unit. In the crystal, the A and B molecules stack head-to-tail in columns along the b-axis direction.
A new series of 2,3-dihydrothiophenes bearing ethyl carbamate moiety (4 a-4 l) was designed and synthesized through a facile synthetic route involving domino ring-opening/recyclization reaction of 1,3-thiazolidinedione. The synthesis was achieved via a novel one-pot four-component reaction of aromatic aldehydes, malononitrile and 1,3-thiazolidinedione, using 4dimethylaminopyridine as base catalyst under ethanol reflux.The molecular structures of the synthesized compounds were elucidated by usual spectroscopic techniques such as FT-IR, 1 H NMR, 13 C NMR and HRMS methods. X-ray diffraction was used to confirm the structures of compounds 4 d and 4 j. Readily available starting materials, atom-efficient routes employing more mild reaction conditions and environmentally benign are the attracting features of this current protocol.
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