127230-11-9Relevant academic research and scientific papers
11a-N-tosyl-5-carbapterocarpans: Synthesis, antineoplastic evaluation and in silico prediction of ADMETox properties
Mendes, Joseane A.,Salustiano, Eduardo J.,Pires, Carulini de S.,Oliveira, Thaís,Barcellos, Julio C.F.,Cifuentes, Jhonny M.C.,Costa, Paulo R.R.,Rennó, Magdalena N.,Buarque, Camilla D.
, p. 585 - 590 (2018)
11a-N-tosyl-5-carbapterocarpans (5a–c and 6a–c), 9-N-tosyl-4,4a,9,9a-tetrahydro-3H-carbazole (7), 11a-N-tosyl-5-carbapterocarpen (8) analogues of LQB-223 (4a), were synthesized through palladium catalyzed azaarylation of substituted dihydronaphtalenes (14a–c) and cyclohexadiene (15), respectively, with N-tosyl-o-iodoaniline (11). In order to understand the role of the N-tosyl moiety for the pharmacological activity, the azacarbapterocarpen (9) was also synthesized by Fischer indol reaction. The structural requirements at the A and D-rings for the antineoplastic activity toward human leukemias and breast cancer cells were evaluated as well. Substitutions on the A-ring of 4a and analogues alter the effect on different breast cancer subtypes. On the other hand, A-ring is not essential for antileukemic activity since compound 7, which does not contain the A-ring, showed efficacy with high selectivity indices for drug-resistant leukemias. On the other hand, substitutions on the D-ring of 4a for fluorine or iodine did not improve the antileukemic activity. In silico studies concerning Lipinskís rule of five, ADMET properties and drug scores of those compounds were performed, indicating good physicochemical properties for all compounds, in special for compound 7.
Synthesis of 11a- N -Arylsulfonyl-5-carbapterocarpans (Tetrahydro-5 H -benzo[ a ]carbazoles) by Azaarylation of Dihydronaphthalenes with o -Iodo- N -(Arylsulfonyl)anilines in Poly(ethylene glycol)
Barcellos, Julio C. F.,Borges, Beatriz H. F.,Mendes, Joseane A.,Ceron, Mauricio C.,Buarque, Camilla D.,Dias, Ayres G.,Costa, Paulo R. R.
, p. 3013 - 3019 (2015/09/28)
11a-N-Arylsulfonyl-5-carbapterocarpans (tetrahydro-5H-benzo[a]carbazoles) were synthesized by palladium-catalyzed azaarylation of dihydronaphthalenes with o-iodo-N-(arylsulfonyl)anilines in poly(ethylene glycol) (PEG-400). Better chemical yields (moderate
Palladium-Catalyzed Heteroannulation of 1,3-Dienes by Functionally Substituted Aryl Halides
Larock, Richard C.,Berrios-Pena, Norman,Narayanan, Kris
, p. 3447 - 3450 (2007/10/02)
Heteroatom-containing aryl iodides react with 1,3-dienes in the presence of a palladium catalyst and an appropriate base to afford a variety of oxygen and nitrogen heterocycles.
