6287-38-3Relevant articles and documents
Synthesis and structure activity relationships of cyanopyridone based anti-tuberculosis agents
Boshoff, Helena I. M.,Caljon, Guy,Forbes, He Eun,Hulpia, Fabian,Jian, Yanlin,Munier-Lehmann, Héle?ne,Risseeuw, Martijn D. P.,Van Calenbergh, Serge
, (2020/07/06)
Mycobacterium tuberculosis, the causative agent of tuberculosis, relies on thymidylate kinase (MtbTMPK) for the synthesis of thymidine triphosphates and thus also DNA synthesis. Therefore, this enzyme constitutes a potential Achilles heel of the pathogen. Based on a previously reported MtbTMPK 6-aryl-substituted pyridone inhibitor and guided by two co-crystal structures of MtbTMPK with pyridone- and thymine-based inhibitors, we report the synthesis of a series of aryl-shifted cyanopyridone analogues. These compounds generally lacked significant MtbTMPK inhibitory potency, but some analogues did exhibit promising antitubercular activity. Analogue 11i demonstrated a 10-fold increased antitubercular activity (MIC H37Rv, 1.2 μM) compared to literature compound 5. Many analogues with whole-cell antimycobacterial activity were devoid of significant cytotoxicity.
The Hydrazine–O2 Redox Couple as a Platform for Organocatalytic Oxidation: Benzo[c]cinnoline-Catalyzed Oxidation of Alkyl Halides to Aldehydes
Stone, Ilana B.,Jermaks, Janis,MacMillan, Samantha N.,Lambert, Tristan H.
supporting information, p. 12494 - 12498 (2018/09/18)
An organocatalytic oxidation platform that capitalizes on the capacity of hydrazines to undergo rapid autoxidation to diazenes is described. Commercially available benzo[c]cinnoline is shown to catalyze the oxidation of alkyl halides to aldehydes in a novel mechanistic paradigm involving nucleophilic attack, prototropic shift, and hydrolysis. The hydrolysis and reoxidation events occur readily with only adventitious oxygen and water. A survey of the scope of viable substrates is shown along with mechanistic and computational studies that give insight into this mode of catalysis.
Tungstate ions (WO4 =) supported on imidazolium framework as novel and recyclable catalyst for rapid and selective oxidation of benzyl alcohols in the presence of hydrogen peroxide
Hosseini Eshbala, Fereshteh,Mohanazadeh, Farajollah,Sedrpoushan, Alireza
, (2017/04/21)
Tungstate salt with imidazolium framework is found to be a recoverable and heterogeneous system favouring the highly selective oxidation of primary benzylic alcohols to corresponding aldehydes with 30% H2O2 as a green oxidant under neutral aqueous reaction conditions. Furthermore, in order to demonstrate the recyclability of the catalyst, it was recovered and efficiently reused in seven succeeding reaction cycles without any significant loss. The use of green solvent, very short reaction time with excellent yields and recyclability of the catalyst make this protocol highly advantageous.
