34897-85-3Relevant articles and documents
Stereochemical issues related to the synthesis of 7,10-dimethyl- 7,10,16,16a-tetrahydro-11H-quinazolino[2',3':3,4]pyrazino-[1,2-b]β- carboline-5,8-diones
Madrigal, Antonio,Grande, Mercedes,Avendano, Carmen
, p. 3115 - 3123 (1998)
Condensation reactions between anthranilic acid and iminoethers derived from 2,3,6,7,12,12a-hexahydropyrazino[1,2-b]β-carboline-1,4-diones 3-8 to give the title hexacyclic compounds were studied from a stereochemical point of view. The configuration was r
'Second-generation' 1,2,3-triazole-based inhibitors of: Porphyromonas gingivalis adherence to oral streptococci and biofilm formation
Patil, Pravin C.,Tan, Jinlian,Demuth, Donald R.,Luzzio, Frederick A.
, p. 268 - 279 (2019/03/02)
Several 'second-generation' click inhibitors of the multi-species biofilm propagated by the adherence of the oral pathogen Porphyromonas gingivalis to Streptococcus gordonii were synthesized and evaluated. The design of the structures was based on the results obtained with the first-generation diphenyloxazole 'click' inhibitors which bear suitable hydrophobic and polar groups within a dual scaffold molecule bearing a 1,2,3-triazole spacer. The structures of the synthetic targets reported herein now consist of a triazolyl(phenylsulfonylmethyl) and a triazolyl(phenylsulfinylmethyl) spacer which joins a 4,5-diphenyloxazole with both phenyl rings bearing lipophilic substituents. The triazolyl "linker" group is formed by a click reaction between the 4-azido(phenylsulfonyl/sulfinylmethyl) oxazoles and acetylenic components having aryl groups bearing hydrophobic substituents. The 1,3,5-trisubstituted-2,4,6-triazine scaffold of the most active click compounds were modeled after the structural motif termed the VXXLL nuclear receptor (NR) box. When substituted at the 3- and 5-positions with 2- and 4-fluorophenylamino and N,N-diethylamino units, the candidates bearing the 1,3,5-trisubstituted-2,4,6-triazine scaffold formed a substantial subset of the second-generation click candidates. Four of the click products, compounds 95, 111, 115 and 122 showed inhibition of the adherence of P. gingivalis to S. gordonii with an IC50 range of 2.3-4.3 μM and only 111 exhibited cytotoxic activity against telomerase immortalized gingival keratinocytes at 60 μM. These results suggest that compounds 95, 115, 122, and possibly 111 represent the most suitable compounds to evaluate for activity in vivo.
Insights into the Desaturation of Cyclopeptin and its C3 Epimer Catalyzed by a non-Heme Iron Enzyme: Structural Characterization and Mechanism Elucidation
Liao, Hsuan-Jen,Li, Jikun,Huang, Jhih-Liang,Davidson, Madison,Kurnikov, Igor,Lin, Te-Sheng,Lee, Justin L.,Kurnikova, Maria,Guo, Yisong,Chan, Nei-Li,Chang, Wei-Chen
supporting information, p. 1831 - 1835 (2018/01/27)
AsqJ, an iron(II)- and 2-oxoglutarate-dependent enzyme found in viridicatin-type alkaloid biosynthetic pathways, catalyzes sequential desaturation and epoxidation to produce cyclopenins. Crystal structures of AsqJ bound to cyclopeptin and its C3 epimer ar
