63274-52-2

Upstream product

• 40106-13-6 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid ethyl ester 
• 98-88-4 benzoyl chloride 
• 502-42-1 cycloheptanone 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 63274-57-7 2-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d][1,3]thiazine-4-thione 
• 107113-13-3 3-Amino-2-phenyl-3,5,6,7,8,9-hexahydro-10-thia-1,3-diaza-benzo[a]azulene-4-thione 
• 105544-24-9 3-(3-Hydroxy-propyl)-2-phenyl-3,5,6,7,8,9-hexahydro-10-thia-1,3-diaza-benzo[a]azulene-4-thione 
• 107113-11-1 2-phenyl-6,7,8,9-tetrahydro-4H,5H-cyclohepta[4,5]thieno[2,3-d][1,3]oxazin-4-one 
• 333774-32-6 2-(benzoylamino)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid 

Relevant academic research and scientific papers

From cycloheptathiophene-3-carboxamide to oxazinone-based derivatives as allosteric HIV-1 ribonuclease H inhibitors

The paper focussed on a step-by-step structural modification of a cycloheptathiophene-3-carboxamide derivative recently identified by us as reverse transcriptase (RT)-associated ribonuclease H (RNase H) inhibitor. In particular, its conversion to a 2-aryl-cycloheptathienoozaxinone derivative and the successive thorough exploration of both 2-aromatic and cycloheptathieno moieties led to identify oxazinone-based compounds as new anti-RNase H chemotypes. The presence of the catechol moiety at the C-2 position of the scaffold emerged as critical to achieve potent anti-RNase H activity, which also encompassed anti-RNA dependent DNA polymerase (RDDP) activity for the tricyclic derivatives. Benzothienooxazinone derivative 22 resulted the most potent dual inhibitor exhibiting IC50s of 0.53 and 2.90 μM against the RNase H and RDDP functions. Mutagenesis and docking studies suggested that compound 22 binds two allosteric pockets within the RT, one located between the RNase H active site and the primer grip region and the other close to the DNA polymerase catalytic centre.