74446-23-4Relevant articles and documents
Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
, p. 181 - 199 (2018)
Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
Design and Construction of a Chiral Cd(II)-MOF from Achiral Precursors: Synthesis, Crystal Structure and Catalytic Activity toward C-C and C-N Bond Forming Reactions
Gupta, Vijay,Mandal, Sanjay K.
, p. 3219 - 3226 (2019/03/28)
Using achiral components, a V-shaped dicarboxylic acid (H2L) and a conformationally flexible bidentate linker (bpp), a thermally stable chiral metal organic framework {[Cd(bpp)(L)(H2O)]·DMF}n (1), where H2L = 4,
Synthesis and histamine H2 agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups
Buschauer, A,Friese-Kimmel A,Baumann, G,Schunack, W
, p. 321 - 330 (2007/10/02)
Analogues of the potent histamine H2 agonist arpromidine, characterized by non-hetrocyclic groups (phenyl, cyclohexyl, alkyl) instead of the pheniramine-like portion, were prepared and tested for their H2 agonistic and H1 antagonistic activity in the isolated guiea pig right atrium and ileum, respectively.In the diphenylpropylguanidine series an increase in H2 agonistic potency resulted from mono- or difluorination at one or both phenyl rings in the meta and/or para position (pD2 7.75 vs pD2 = 7.15 for the unsubstituted parent compound).Compounds chlorinated atboth phenyl rings were considerably less potent.Highest combined H2 agonistic/H1 antagonistic potency was found in the 4-fluorophenyl series.The arpromidine analogue with cyclohexyl and methyl group instead of phenyl and pyridine ring proved to be 30 times more potent than histamine in the atrium.The H1 antagonistic potency in cyclohexyl compounds was lower than in the diaryl series.Thus, aromatic rings appear not to be required for high H2 agonistic potency but are useful for combined H2 agonistic/H1 antagonistic activity. histamine / H2 receptor / H2 agonist / arpromidine / impromidine / H1 antagonist / antihistamine
