Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation

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Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation Publisher

Ebrahimi SES¹ ; Ghadirian P¹ ; Emtiazi H² ; Yahyameymandi A¹ ; Saeedi M^{3, 4} ; Mahdavi M⁵ ; Nadri H⁶ ; Moradi A⁶ ; Sameem B¹ ; Vosooghi M⁷ ; Emami S⁸ ; Foroumadi A⁹ ; Shafiee A⁹

Show Affiliations

1. School of Pharmacy, Tehran University of Medical Sciences, International Campus (TUMS- IC), Tehran, Iran
2. Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
3. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
4. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
5. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
6. Department of Medicinal Chemistry, Faculty of Pharmacy and Neurobiomedical Research Center, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
7. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
8. Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran
9. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Medicinal Chemistry Research Published:2016

Abstract

A series of chromene-fused coumarins known as 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones 4a–o were synthesized through one-pot reaction of appropriate benzaldehydes, dimedone, and 4-hydroxycoumarin in the presence of nano-silica sulfuric acid under solvent-free condition in good yields. The in vitro anticholinesterase assay revealed that the 3-hydroxyphenyl analog 4e showed the highest inhibitory activity against both acetylcholinesterase and butyrylcholinesterase, possessing IC50 values of 3.28 and 2.19 µM, respectively. The structure-activity relationships study demonstrated that the selectivity for acetylcholinesterase over butyrylcholinesterase could be modulated by introducing second hydroxyl or methoxy substituent on the para-position of the 3-hydroxyphenyl pendent group. The docking study of compound 4e with acetylcholinesterase confirmed π–π stacking interaction between the coumarin moiety and Trp279 as well as the formation of hydrogen bonding between hydroxyl group and Asn85. © 2016, Springer Science+Business Media New York.

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Style	Citing Format
MLA	Ebrahimi SES, et al.. "Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation." Medicinal Chemistry Research, vol. 25, no. 9, 2016, pp. 1831-1841.
APA	Ebrahimi SES, Ghadirian P, Emtiazi H, Yahyameymandi A, Saeedi M, Mahdavi M, Nadri H, Moradi A, Sameem B, Vosooghi M, Emami S, Foroumadi A, Shafiee A (2016). Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation. Medicinal Chemistry Research, 25(9), 1831-1841.
Chicago	Ebrahimi SES, Ghadirian P, Emtiazi H, Yahyameymandi A, Saeedi M, Mahdavi M, Nadri H, et al.. "Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation." Medicinal Chemistry Research 25, no. 9 (2016): 1831-1841.
Harvard	Ebrahimi SES et al. (2016) 'Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation', Medicinal Chemistry Research, 25(9), pp. 1831-1841.
Vancouver	Ebrahimi SES, Ghadirian P, Emtiazi H, Yahyameymandi A, Saeedi M, Mahdavi M, et al.. Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation. Medicinal Chemistry Research. 2016;25(9):1831-1841.
BibTex	@article{ author = {Ebrahimi SES and Ghadirian P and Emtiazi H and Yahyameymandi A and Saeedi M and Mahdavi M and Nadri H and Moradi A and Sameem B and Vosooghi M and Emami S and Foroumadi A and Shafiee A}, title = {Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation}, journal = {Medicinal Chemistry Research}, volume = {25}, number = {9}, pages = {1831-1841}, year = {2016} }
RIS	TY - JOUR AU - Ebrahimi SES AU - Ghadirian P AU - Emtiazi H AU - Yahyameymandi A AU - Saeedi M AU - Mahdavi M AU - Nadri H AU - Moradi A AU - Sameem B AU - Vosooghi M AU - Emami S AU - Foroumadi A AU - Shafiee A TI - Hetero-Annulated Coumarins As New Ache/Buche Inhibitors: Synthesis and Biological Evaluation JO - Medicinal Chemistry Research VL - 25 IS - 9 SP - 1831 EP - 1841 PY - 2016 ER -

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