6500-51-2Relevant academic research and scientific papers
Site-Selective Functionalization of (sp3)C?H Bonds Catalyzed by Artificial Metalloenzymes Containing an Iridium-Porphyrin Cofactor
Gu, Yang,Natoli, Sean N.,Liu, Zhennan,Clark, Douglas S.,Hartwig, John F.
, p. 13954 - 13960 (2019/08/30)
The selective functionalization of one C?H bond over others in nearly identical steric and electronic environments can facilitate the construction of complex molecules. We report site-selective functionalizations of C?H bonds, differentiated solely by rem
Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: Toward the emergence of new building blocks
Moitessier, Clémence,Rifai, Ahmad,Danjou, Pierre-Edouard,Mallard, Isabelle,Cazier-Dennin, Francine
, p. 721 - 726 (2019/04/17)
4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of complex molecular architectures. Nevertheless, literature generally describes their synthesis in very low yield (below 5%), mainly due to the inefficiency of the last oxidation step. In this paper, we report a reliable synthesis of 4-substituted-ortho-phthalaldehyde analogues in 51% overall yield owing to the addition of a protecting step of the unstable key intermediate 4,5-dihydroisobenzofuran-5-ol. Oxidation and deprotection steps were also studied in order to provide an effective availability of these two dialdehyde compounds that may increase their future applications.
Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
, p. 224 - 239 (2017/12/08)
One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.
Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action
Parrino, Barbara,Carbone, Anna,Ciancimino, Cristina,Spanò, Virginia,Montalbano, Alessandra,Barraja, Paola,Cirrincione, Girolamo,Diana, Patrizia,Sissi, Claudia,Palumbo, Manlio,Pinato, Odra,Pennati, Marzia,Beretta, Giovanni,Folini, Marco,Matyus, Peter,Balogh, Balázs,Zaffaroni, Nadia
, p. 149 - 162 (2015/03/18)
Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progression and inducing apoptosis in cancer cells. These effects were associated to IIQ-mediated impairment of tubulin polymerization at pharmacologically significant concentrations of tested compounds. In addition, impaired DNA topoisomerase I functions and perturbation in telomere architecture were observed in cells exposed to micromolar concentrations of IIQ derivatives. The above results suggest that IIQ derivatives exhibit multi-target cytotoxic activities.
Efficient synthesis of selected phthalazine derivatives
Bunce, Richard A.,Harrison, Todd,Nammalwar, Baskar
, p. 123 - 126 (2013/01/16)
Four phthalazine derivatives have been prepared from substituted 2-bromobenzaldehyde acetals by a sequence involving: (1) lithiation and formylation; (2) deprotection; and (3) condensative cyclization with hydrazine. Two additional phthalazines were prepa
7-Methoxy-3-nitro-2-naphthalenemethanol - A new phototrigger for caging applications
Singh, Anil K.,Khade, Prashant K.
, p. 4899 - 4902 (2011/10/05)
Synthesis, photochemistry and photorelease properties of 7-methoxy-3-nitro-2-naphthalenemethanol (MNNM) are described. Photoirradiation (≥370 nm) of MNNM covalently linked to hippuric acid causes efficient release (～90%) of hippuric acid.
NHC-catalyzed spiro bis-indane formation via domino stetter - Aldol - Michael and stetter - Aldol - Aldol reactions
Sanchez-Larios, Eduardo,Holmes, Janice M.,Daschner, Crystal L.,Gravel, Michel
supporting information; experimental part, p. 5772 - 5775 (2011/03/22)
Two novel domino NHC-catalyzed spirocyclizations are described herein, enabling the rapid construction of three new carbon - carbon bonds and a quaternary center with high diastereoselectivity. A variety of spiro bis-indane structures are assembled in a single step from simple o-phthaldialdehyde derivatives.
A convenient access to benzo-substituted phthalazines as potential precursors to DNA intercalators
Tsoungas, Petros G,Searcey, Mark
, p. 6589 - 6592 (2007/10/03)
2-Nitro-5-methoxybenzaldehyde is converted to amines 2 and 7 via two alternative routes. Upon diazotisation and Sandmeyer reaction, halides 4 and 9 are formed, which, through lithiation and formylation lead to the o-phthalaldehyde. Further cyclisation with hydrazine gives the 5-methoxy-substituted phthalazine.
The Oxidation of a Series of Phthalyl Alcohols
Bhattacharjee, Debkumar,Popp, Frank D.
, p. 315 - 320 (2007/10/02)
A series of phthalyl alcohols containing methoxy and methyl substituents were prepared by lithium aluminum hydride reduction of phthalides.Oxidation of the phthalyl alcohols with activated manganese dioxide or with barium manganate gave phthalaldehydes or
