Papers by Author: Qi Sun

Abstract: Two adenosine-containing asymmetrical dinucleoside triphosphates were synthesized via the P(V)–N activation method. The key adenosine 5ʹ-phosphoropiperidate intermediate was obtained by a redox condensation method. The reaction of adenosine phosphoropiperidate with uridine 5ʹ- and cytidine 5ʹ-diphosphates in the presence of 4,5-dicyanoimidazole (DCI) afforded the desired dinucleoside triphosphates in good isolated yields.

Abstract: A series of α-aminophosphonate-functionalized 3-aminopropanols have been efficiently prepared and characterized by ¹H, ¹³C, and ³¹P NMR and mass spectroscopy. The reaction conditions such as solvent and temperature were thoroughly investigated based on the three-component Kabachnik-Fields reaction. The experimental results revealed that moderate elevation of reaction temperature under solvent-free conditions was optimal for the synthesis of these types of compounds without forming the cyclized byproduct.

Abstract: A three-component solvent-free method for the synthesis of a series of bis-α-aminophosphonate-modified butanes has been developed. The experimental results showed that the solvent-free reaction conditions without catalyst were optimal for the preparation of this type compounds. The synthesized title compounds were characterized by ¹H, ¹³C, and ³¹P NMR and mass spectroscopy.

Abstract: A facile and efficient method for the synthesis of P¹,P³-dizidovudine-5′,5′-triphosphate has been developed. The coupling of zidovudine diphosphate with zidovudine phosphoropiperidate based on the DCI activation of P-N bond afforded the desired product in good yield.

Abstract: A new ZrCl₄-catalyzed method for the preparation of an asymmetrical benzimidazole derivative has been developed. Further alkylation of the benzimidazole precursor with methyl iodide afforded a new monomethine cyanine derivative. The photophysical evaluation showed that the newly synthesized monomethine cyanine compound was non-fluorescent.

Abstract: An improved method for the synthesis of α-aminophosphonate based on the Kabachnik-Fields reaction has been developed. The Kabachnik-Fields reactions for the synthesis of the title compounds were investigated in different solvents. The results showed that the solvent-free conditions was optimal for synthesis of this type of compounds.

Abstract: A novel and efficient method for the preparation of P¹-AZT-5′-P³-d4T-5′-triphosphate has been developed. The title compound was characterized with ¹H, ¹³C, and ³¹P NMR and mass spectrometry. The experimental results indicated that the employment of 4,5-dicyanoimidazole (DCI) as the activator could notably promote the coupling reaction of AZT 5′-phosphoropiperidate and d4T 5′-diphosphate.

Abstract: A facile method for the one-pot preparation of homodinucleotides of AZT and d4T from corresponding nucleoside 5′-phosphoropiperidates with 4,5-dicyanoimidazole (DCI) as the activator has been developed.

Abstract: An efficient method for the synthesis of 5-formyl-2′-deoxycytidine and its monophosphate has been developed.

Abstract: The N-methylphenylamino group conjugated to the 2 position of the benzimidazolium core via a vinyl group in the structure of AKT inhibitor IV was efficiently substituted by treating AKT inhibitor IV with excess of N-methylcyclohexanamine and N-methylbenzylamine. The two new compounds were characterized by ¹H and ¹³C NMR, IR, and mass spectroscopy. The control experiment with benzimidazole precursor of AKT inhibitor IV resulted in no amine-exchange reaction, indicating that the positive charge in the benzimidazolium salt is the major factor for the activation of the terminal conjugated N-methylphenylamino group.