Design, Synthesis, and Biological Evaluation of Novel Tetrahydroacridin Hybrids with Sulfur-Inserted Linkers as Potential Multitarget Agents for Alzheimer's Disease – PubMed Black Hawk Supplements

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Alzheimer’s disease (AD) is a complex neurodegenerative disease that can lead to the loss of cognitive function. The progression of AD is regulated by multiple signaling pathways and their associated targets. Therefore, multitarget strategies theoretically have greater potential for treating AD. In this work, a series of new hybrids were designed and synthesized by the hybridization of tacrine (4, AChE: IC(50) = 0.223 μM) with pyrimidone compound 5 (GSK-3β: IC(50) = 3 μM) using the cysteamine or…
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Design, Synthesis, and Biological Evaluation of Novel Tetrahydroacridin Hybrids with Sulfur-Inserted Linkers as Potential Multitarget Agents for Alzheimer's Disease - PubMed

Scheme 1

Synthesis of compounds 16a16f and 18a18c. (a) (i) CDI, THF, 66 °C, 1–2 h and (ii) MgCl2, ethyl potassium malonate, THF, 66 °C, 10 h, 45–50% yield; (b) EtOH, N-methylthiourea, DBU, 80 °C, 12 h 42–45% yield; (c) DCE, DMF, POCl3, 65 °C, 1.5 h, 48–53% yield; (d) (i) 2 N NaOH aqueous solution, 25 °C, 8 h and (ii) HCl, 25 °C, 20 min, 90–93% yield; (e) POCl3, cyclohexanone, 110 °C, 4 h, 75–80% yield; (f) n-pentanol, K2CO3, 2-bromoethylamine hydrobromide, 99 °C, 12 h, 50–55% yield; (g) CH3CN, K2CO3, 85 °C, 12 h, 45–50% yield; (h) n-pentanol, K2CO3, cystamine dihydrochloride, 99 °C, 12 h, 45–50% yield; and (i) CH3CN, K2CO3, 85 °C, 12 h, 43–47% yield.

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Design, Synthesis, and Biological Evaluation of Novel Tetrahydroacridin Hybrids with Sulfur-Inserted Linkers as Potential Multitarget Agents for Alzheimer's Disease – PubMed