Conformationally Locked Carbocyclic Nucleosides Built on a 4′-Hydroxymethyl-3′-hydroxybicyclo[4.1.0]heptane Template. Stereoselective Synthesis and Antiviral Activity

Abstract

Two new families of enantiomerically pure carbocyclic nucleoside analogues based on a cyclohexane moiety with five chiral centers and a fused cyclopropyl ring have been synthesized. A highly regio-and stereoselective synthetic approach for the modular construction of the functionalized bicyclo[4.1.0]heptyl azide intermediate 6 has been established. Key steps to achieve this asymmetric synthesis involved highly diastereoselective allylic oxidation and hydroboration reactions. The first family of compounds, 1a,b and 2, presents different natural nucleobases, whereas the second one 3a−e bears functionalized 1,2,3-triazoles. These derivatives have been tested as antiviral agents, and compound 3d has shown to display moderate activity against coxsackie B4 virus.

Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

“…[66] Although it is achiral, it has been employed in several substrate-controlled diastereoselective hydroxylations. Examples include key steps in the synthesis of ryanodine and ryanodol (Reisman et al), [67] nucleosides (Busqué and Alibés and co-workers), [68] the hepatitis B drug entecavir (Huang et al), [69] the poison frog alkaloid chiriquitoxin (Nishikawa et al), [70] steroids (Ghosh et al) [71] and vitamin D 3 analogues (De Luca et al). [72] 6.…”

“…Examples include key steps in the synthesis of ryanodine and ryanodol (Reisman et al. ), [67] nucleosides (Busqué and Alibés and co‐workers), [68] the hepatitis B drug entecavir (Huang et al. ), [69] the poison frog alkaloid chiriquitoxin (Nishikawa et al.…”

Synthesis and evaluation of photophysical, electrochemical, and ROS generation properties of new chalcogen-naphthoquinones-1,2,3-triazole hybrids

“…Another prominent scaffold is the 1,2,3-triazole nucleus who have a wide range of applications, including explosives, agrochemicals, and mostly medicines. 19 Due to the biological activities associated with the 1,2,3-triazole ring, it is used as an important linker in new pharmacologically active molecules and showed properties such as anti-inflammatory, 20 anticonvulsant, 21 antioxidant, 22 antibacterial, 23 antiviral, 24 antifungal, 25 anti- T. cruzi ( Trypanosoma cruzi ), 26 antitubercular, 27 anticancer, 28 anti-HIV (Human Immunodeficiency Virus), 29 and anti-Alzheimer. 30 Moreover, the distinct electronic structure of this ring, along with its polydentate nature, allows it to effectively bind to metal ions and analytes, making it an ideal choice for chemosensors used in qualitative and quantitative studies.…”