364070-25-7Relevant academic research and scientific papers
Synthesis and in vitro cytotoxic evaluation of 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives
Cao, Rihui,Peng, Wenlie,Chen, Hongsheng,Hou, Xuerui,Guan, Huaji,Chen, Qi,Ma, Yan,Xu, Anlong
, p. 249 - 257 (2005)
A series of novel 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives was synthesized from the starting material l-tryptophan. Cytotoxic activities of these compounds were investigated in vitro. The results showed that 1,3,9-trisubstituted β-carboline derivatives had higher cytotoxic activities in vitro than the corresponding 1,3-bisubstituted compounds. Among all the synthesized 1,3,9-trisubstituted β-carboline derivatives, the compounds with a methyl substituent at position-1 displayed more potent cytotoxic activities, furthermore compound 5e having an ethoxycarbonyl substituent at position-3 and a pentafluorobenzyl at position-9, respectively, was found to be the most potent compounds of this series with IC50 value of 4:uM against BGC-823 cell lines. These data suggested that (1) the cytotoxic potencies of β-carboline derivatives were enhanced by the introduction of appropriate substituents into position-1 and position-9 in β-carboline; (2) the β-carboline structure might be an important basis for the design and synthesis of new antitumor drugs; (3) the methyl substituent at position-1, the pentafluorobenzyl group at position-9 and the ethoxycarbonyl substituent at position-3 were the optimal combination for the improvement of cytotoxic activity of the β-carboline derivatives.
Synthesis and antiviral activity of β-carboline derivatives bearing a substituted carbohydrazide at C-3 against poliovirus and herpes simplex virus (HSV-1)
Nazari Formagio, Anelise S.,Santos, Patricia R.,Zanoli, Karine,Ueda-Nakamura, Tania,Duesman Tonin, Lilian T.,Nakamura, Celso V.,Sarragiotto, Maria Helena
body text, p. 4695 - 4701 (2009/12/28)
Several novel 1,3-disubstituted β-carboline derivatives bearing a substituted carbohydrazide group at C-3 were synthesized and evaluated for their antiviral activity against vaccinal poliovirus (VP) and herpes simplex virus type 1 (HSV-1). The cytotoxicity and selectivity index of the active compounds were also evaluated. Among the synthesized derivatives, compounds 10 and 11 displayed potent activity against both vaccinal poliovirus and HSV-1 virus. Compound 10 presented the highest selectivity index (SI = 2446.8) against HSV-1 virus and low cytotoxicity (CC50 = 1150.0 ± 67.3 μM). The virus yield inhibition assay showed that compound 10 was able to inhibit HSV-1 plaque formation before and during the virus adsorption. The characteristic small plaque pattern observed in compound-treated cells suggested that compound 10 inhibited viral dissemination to neighboring cells. A computational study for prediction of ADME properties of the novel synthesized β-carbolines derivatives was performed by determination of lipophilicity, topological polar surface area (TPSA), absorption (% ABS) and simple molecular descriptors, using Lipinski′s rule.
Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl) β-carboline derivatives
Formagio, Anelise S. Nazari,Tonin, Lilian T. Duesman,Foglio, Mary Ann,Madjarof, Christiana,de Carvalho, Joao Ernesto,da Costa, Willian Ferreira,Cardoso, Flavia P.,Sarragiotto, Maria Helena
body text, p. 9660 - 9667 (2009/04/06)
Several novel 1-substituted-phenyl β-carbolines bearing the 2-substituted-1,3,4-oxadiazol-5-yl and 5-substituted-1,2,4-triazol-3-yl groups at C-3 were synthesized and evaluated for their in vitro anticancer activity. The assay results pointed thirteen compounds with growth inhibition effect (GI50 50 values lying in the nanomolar concentration range (GI50 = 10 nM for both compounds). The 1-(N,N-dimethylaminophenyl)-3-(5-thioxo-1,2,4-triazol-3-yl) β-carboline (8g) was the most active compound, showing particular effectiveness on lung (GI50 = 0.06 μM), ovarian and renal cell lines. The potent anticancer activity presented for synthesized compounds 7a, 7h, and 8g, together with their easiness of synthesis, makes these compounds promising anticancer agents.
