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A new efficient synthesis of pyrano[2,3-b]quinoline derivatives is developed via the H2SO4-mediated tandem cyclization/ring-opening/recyclization reaction of readily available 1-acetyl N-aryl cyclopentanecarboxamides, during which a novel ring-cleavage fashion of the cyclopentane unit is involved and possible mechanisms are discussed.

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A SnCl4.5H2O-mediated facile and efficient one-step synthesis of the tricyclic core of martinellic acid from readily available 2-(cyanomethyl)-3-oxo-N-arylbutanamides was developed and a mechanism involving consecutive hydrolysis of a cyano group and a double annulation process is proposed.

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A series of conformationally restricted dihydro-alkylthio-benzyl-oxopyrimidine (S-DABO) hybrids, which combined the structural features of C6-a-methylbenzyl-thio-DABOs (a-methyl-S-DABOs) and C6-acyanobenzyl-thio-DABOs (CN-S-DABOs), has been synthesized and biologically evaluated for their anti-HIV activity against wild-type HIV-1 strain IIIB, double RT mutant (K103N + Y181C) strain RES056and HIV-2 strain ROD in MT-4 cell cultures. Most of these compounds exhibited inhibitory activity (wild-type) within the range of EC 50 values from micromolar to nanomolar. Among them, compound 1s displayed the highest anti-HIV-1 activity with an EC 50 value of 91 nM and a selectivity index (SI) of 548, which was more potent than zalcitabine and comparable to nevirapine and delavirdine in the same assay. The HIV-1 reverse transcriptase inhibitory (RT) assay confirmed that these conformationally restricted S-DABO hybrids targeted HIV-1 RT. The preliminary structure-activity relationship (SAR) and molecular docking analysis of this new series of conformationally constrained CN-S-DABO hybrids were also investigated.

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