26452-80-2Relevant articles and documents
Deaminative chlorination of aminoheterocycles
Cornella, Josep,Faber, Teresa,Gómez-Palomino, Alejandro,Ghiazza, Clément
, (2021/12/23)
Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]
Small molecule inhibitors of anthrax edema factor
Jiao, Guan-Sheng,Kim, Seongjin,Moayeri, Mahtab,Thai, April,Cregar-Hernandez, Lynne,McKasson, Linda,O'Malley, Sean,Leppla, Stephen H.,Johnson, Alan T.
supporting information, p. 134 - 139 (2017/12/06)
Anthrax is a highly lethal disease caused by the Gram-(+) bacteria Bacillus anthracis. Edema toxin (ET) is a major contributor to the pathogenesis of disease in humans exposed to B. anthracis. ET is a bipartite toxin composed of two proteins secreted by the vegetative bacteria, edema factor (EF) and protective antigen (PA). Our work towards identifying a small molecule inhibitor of anthrax edema factor is the subject of this letter. First we demonstrate that the small molecule probe 5′-Fluorosulfonylbenzoyl 5′-adenosine (FSBA) reacts irreversibly with EF and blocks enzymatic activity. We then show that the adenosine portion of FSBA can be replaced to provide more drug-like molecules which are up to 1000-fold more potent against EF relative to FSBA, display low cross reactivity when tested against a panel of kinases, and are nanomolar inhibitors of EF in a cell-based assay of cAMP production.
Dehalogenation degradation method for halogenated pyridine compound
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Paragraph 0023; 0024, (2016/12/16)
The invention provides a dehalogenation degradation method for a halogenated pyridine compound. The halogenated pyridine compound is adopted as a raw material, alcohol is adopted as a hydrogen source, water is adopted as a solvent, reacting is carried out for 3-10 h under normal pressure at the temperature of 20 DEG C to 120 DEG C under the action of a supported catalyst, and the halogenated pyridine compound is subjected to dehalogenation degradation in situ through water phase hydrogen production. A pyridine ring of the halogenated pyridine compound at least contains an F or Cl or Br or I substituent group. The supported catalyst is composed of an active component and a carrier, the active component is composed of a mixture of transition metal and other metal, the transition metal is one of Rh, Pd, Pt and Ni, and other metal is one of Se, Ca, Ba, La and Ce. The carrier is one of activated carbon, kieselguhr, zeolite, gamma-Al2O3, AlF3 and MgO. H2 is not directly used as a reduction agent, activated hydrogen is prepared through in-situ catalysis to directly participate in reacting, the advantages of being high in reaction activity, high in selectivity, high in safety, environmentally friendly and the like are achieved, and good application prospects are achieved.
