140920-82-7Relevant academic research and scientific papers
Synthesis and antitumor activity of novel: N -substituted tetrahydro-β-carboline-imidazolium salt derivatives
Zhou, Bei,Liu, Zheng-Fen,Deng, Guo-Gang,Chen, Wen,Li, Min-Yan,Yang, Li-Juan,Li, Yan,Yang, Xiao-Dong,Zhang, Hong-Bin
, p. 9423 - 9430 (2016)
The synthesis of a series of novel N-substituted tetrahydro-β-carboline-imidazolium salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24-8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
Formal synthesis of (±) —quebrachamine through regio- and stereoselective hydrocyanation of arylallene
Matsumoto, Koki,Arai, Shigeru,Nishida, Atsushi
supporting information, p. 2865 - 2870 (2018/05/07)
This article describes the formal synthesis of quebrachamine based on regio- and stereoselective hydrocyanation of 1,3-disubstituted allenes. Allenyl C–C double bonds are effectively discriminated through Ni-catalyzed hydrocyanation and a CN group is utilized as a synthon of piperidine ring. Several steps from HCN adduct afforded known intermediates to quebrachamine.
Enantioselective Model Synthesis and Progress toward the Putative Structure of Yuremamine
Ghosh, Avipsa,Bainbridge, David T.,Stanley, Levi M.
, p. 7945 - 7951 (2016/09/12)
An enantioselective model synthesis of the 2,3-dihydro-1H-pyrrolo[1,2-a]indole core of the putative structure of yuremamine is reported in 39% overall yield and 96% ee over five steps. The model synthesis leverages enantioselective, rhodium-catalyzed hydroacylation of an N-vinylindole-2-carboxaldehyde as the key step in the installation of the stereochemical triad. An enantioselective synthesis of a densely functionalized dihydropyrroloindolone that maps onto the putative structure of yuremamine is demonstrated in 26% yield and 97% ee over eight steps.
Binap-silver salts as chiral catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes
Mancebo-Aracil, Juan,Martin-Rodriguez, Maria,Najera, Carmen,Sansano, Jose M.,Costa, Paulo R.R.,De Lima, Evanoel Crizanto,Dias, Ayres G.
, p. 1596 - 1606 (2013/02/23)
Binap-AgSbF6 catalyzed 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes are described and compared with analogous transformations mediated by other Binap-silver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfo
De novo design and synthesis of somatostatin non-peptide peptidomimetics utilizing β-D-glucose as a novel scaffolding
Hirschmann, Ralph,Nicolaou,Pietranico, Sherrie,Leahy, Ellen M.,Salvino, Joseph,Arison, Byron,Cichy, Maria A.,Grant Spoors,Shakespeare, William C.,Sprengeler, Paul A.,Hamley, Peter,Smith III, Amos B.,Reisine, Terry,Raynor, Karen,Maechler, Laurie,Donaldson, Cindy,Vale, Wylie,Freidinger, Roger M.,Cascieri, Margaret R.,Strader, Catherine D.
, p. 12550 - 12568 (2007/10/02)
Non-peptide peptidomimetics of the peptide hormone somatostatin (SRIF) were designed and synthesized, utilizing β-D-glucose as a novel scaffolding. Such compounds resemble conventional peptide analogs in that they retain critical amino acid side chains bu
