5930-92-7Relevant articles and documents
Synthesis and X-ray structure of stable 2H-isoindoles
Murashima, Takashi,Tamai, Ryuji,Nishi, Keiji,Nomura, Kentaroh,Fujita, Ken-Ichi,Uno, Hidemitsu,Ono, Noboru
, p. 995 - 998 (2000)
Stable 2H-isoindoles with electron-withdrawing groups were prepared using the reaction of dinitrobenzene derivatives with isocyanoacetate in the presence of DBU. The use of acetonitrile as the solvent or a phosphazene base (BTPP) as a non-ionic base improved the yields. The structure was confirmed by X-ray crystallographic analysis of the compound 2e′. According to the X-ray analysis, this substance existed in the solid phase only as the 2H-isomer. The Royal Society of Chemistry 2000.
New synthetic equivalent of nitromalonaldehyde treatable in organic media
Nishiwaki, Nagatoshi,Ogihara, Takuma,Takami, Toshiko,Tamura, Mina,Ariga, Masahiro
, p. 8382 - 8386 (2007/10/03)
β-Nitroenamines having a formyl group at the β-position behave as the synthetic equivalent of unstable nitromalonaldehyde, which is a useful synthon for syntheses of versatile nitro compounds. High solubility of the nitroenamines into general organic solv
Recognition of the DNA minor groove by pyrrole-imidazole polyamides: Comparison of desmethyl- and N-methylpyrrole
Bremer, Ryan E.,Szewczyk, Jason W.,Baird, Eldon E.,Dervan, Peter B.
, p. 1947 - 1955 (2007/10/03)
Polyamides consisting of N-methylpyrrole (Py), N-methylimidazole (Im), and N-methyl-3-hydroxypyrrole (Hp) are synthetic ligands that recognize predetermined DNA sequences with affinities and specificities comparable to many DNA-binding proteins. As derivatives of the natural products distamycin and netropsin, Py/Im/Hp polyamides have retained the N-methyl substituent, although structural studies of polyamide:DNA complexes have not revealed an obvious function for the N-methyl. In order to assess the role of the N-methyl moiety in polyamide:DNA recognition, a new monomer, desmethylpyrrole (Ds), where the N-methyl moiety has been replaced with hydrogen, was incorporated into an eight-ring hairpin polyamide by solid-phase synthesis. MPE footprinting, affinity cleavage, and quantitative DNase I footprinting revealed that replacement of each Py residue with Ds resulted in identical binding site size and orientation and similar binding affinity for the six-base-pair (bp) target DNA sequence. Remarkably, the Ds-containing polyamide exhibited an 8-fold loss in specificity for the match site versus a mismatched DNA site, relative to the all-Py parent. Polyamides with Ds exhibit increased water solubility, which may alter the cell membrane permeability properties of the polyamide. The addition of Ds to the repertoire of available monomers may prove useful as polyamides are applied to gene regulation in vivo. However, the benefits of Ds incorporation must be balanced with a potential loss in specificity. Copyright (C) 2000 Elsevier Science Ltd.