60117-49-9Relevant academic research and scientific papers
Catalytic Asymmetric Synthesis of 3,3′-Bisindoles Bearing Single Axial Chirality
Chen, Ke-Wei,Wang, Zhao-Shan,Wu, Ping,Yan, Xin-Yu,Zhang, Shu,Zhang, Yu-Chen,Shi, Feng
, p. 10152 - 10166 (2020/09/03)
A catalytic asymmetric synthesis of 3,3′-bisindoles bearing single axial chirality has been established via chiral phosphoric acid (CPA)-catalyzed enantioselective addition reaction of 3,3′-bisindoles with ninhydrin-derived 3-indolylmethanols. The selection of ninhydrin-derived 3-indolylmethanols as suitable electrophiles is based on the consideration that the symmetric and bulky moiety of ninhydrin would increase the steric congestion around the axis to generate stable axial chirality and avoid the generation of central chirality. By this approach, a series of 3,3′-bisindoles bearing single axial chirality were synthesized via the dynamic kinetic resolution (DKR) process in generally acceptable yields and considerable enantioselectivities. In addition, an in-depth investigation on the property (stability and rotation barrier) of the synthesized axially chiral 3,3′-bisindoles was carried out, thus providing useful information on this class of axially chiral frameworks. This approach makes use of the strategy of dynamic kinetic resolution of 3,3′-bisindoles, therefore expanding the generality and applicability of this strategy for catalytic asymmetric synthesis of 3,3′-bisindoles bearing single axial chirality.
Indanediones-1,3 VIII. Hydroxy-2 indolyl-2 indanediones-1,3, (indolyl-3 methylene)-2 indanediones-1,3 et derives: recherche d'une activite anti-inflammatoire
Courant, Jacqueline,Leblois, Danielle,Tandon, Manju,Robert-Piessard, Sylvie,le Baut, Guillaume,et al.
, p. 145 - 154 (2007/10/02)
1,3-Indandiones VIII. 2-Hydroxy-2-indolyl-1,3-indandiones, 2-(indol-3-ylmethylene indandione and derivatives: search for anti-inflammatory activity.A series of 2-hydroxy-2-indolyl-1,3-indandiones, diversely substituted on the heterocycle were synthetized in order to study their anti-inflammatory activity.Catalytic hydrogenation gave 2,3-dihydroxy-1 indanones 6 and NaBH4 reduction of 3i led to the corresponding indanetriol 7i.Base-catalyzed isomerization of hydroxy-β-diketones 3 furnished 3-indololylcarbonyl phthalides 9.Only compound 3d exhibited a significant inhibition of mouse paw edema.Experimentation in the rat paw edema test confirmed the anti-inflammatory effect of 3d, but it was associated with an anti-coagulant activity. ω-Amino-alkylation of the indole nitrogen of 3d led to loss of anti-inflammatory activity.Introduction of a double bond between the indandione and indole nuclei, leading to 2-(indol-3-ylmethylene)-1,3 indandiones 12, proved ineffective in raising this activity. 2-hydroxy-2-indolyl-1,3-indandiones/ 2,3-dihydroxyindanones/ 1,2,3-indantriols/ 3-indolylcarbonyl-phthalides/ 2-(indol-3-ylmethylene)-1,3-indandiones/ anti-inflammatory activity/ anti-coagulant activity
