1338254-52-6

Basic information

• Product Name: N-(2-bromo-5-chloro-benzyl)-2,2-diethoxy-acetamidine
• CAS NO: 1338254-52-6
• Molecular Weight: 349.655
• Mol File: 1338254-52-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(2-bromo-5-chloro-benzyl)-2,2-diethoxy-acetamidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-bromo-5-chloro-benzyl)-2,2-diethoxy-acetamidine(1338254-52-6)
• EPA Substance Registry System: N-(2-bromo-5-chloro-benzyl)-2,2-diethoxy-acetamidine(1338254-52-6)

Safety Data

• Hazardous Substances Data: 1338254-52-6(Hazardous Substances Data)

Upstream product

• 942400-60-4 1-(2-bromo-5-chlorophenyl)methanamine 
• 76742-48-8 2,2-diethoxy-ethanimidic acid methyl ester 

Downstream Products

• 1338257-36-5 3-[5-chloro-3-(3-ethyl-ureido)-isoquinolin-8-ylamino]-benzoic acid tert-butyl ester 

Relevant articles and documents

Discovery and Optimization of Isoquinoline Ethyl Ureas as Antibacterial Agents

Our strategy to combat resistant bacteria consisted of targeting the GyrB/ParE ATP-binding sites located on bacterial DNA gyrase and topoisomerase IV and not utilized by marketed antibiotics. Screening around the minimal ethyl urea binding motif led to the identification of isoquinoline ethyl urea 13 as a promising starting point for fragment evolution. The optimization was guided by structure-based design and focused on antibacterial activity in vitro and in vivo, culminating in the discovery of unprecedented substituents able to interact with conserved residues within the ATP-binding site. A detailed characterization of the lead compound highlighted the potential for treatment of the problematic fluoroquinolone-resistant MRSA, VRE, and S. pneumoniae, and the possibility to offer patients an intravenous-to-oral switch therapy was supported by the identification of a suitable prodrug concept. Eventually, hERG K-channel block was identified as the main limitation of this chemical series, and efforts toward its minimization are reported.

3-UREIDOISOQUINOLIN-8-YL DERIVATIVES

The invention relates to 3-ureidoisoquinolin-8-yl derivatives of formula I I wherein R is alkyl, haloalkyl or cyclopropyl; R 2 is H, halogen, pyridazin-4-yl, pyrimidin-5-yl or an optionally substituted pyridin-3-yl, pyridin-4-yl or phenyl group; R 3 is alkyl, alkynyl, aminoalkyl, carbamoylalkyl, methylcarbamoylalkyl, alkoxy, haloalkoxy, alkynyloxy, (4-hydroxybut-2-yn-1-yl)oxy, (4-aminobut-2-yn-1-yl)oxy, dimethylaminoalkoxy, carbamoylalkoxy, alkylamino, cycloalkyl, cycloalkylalkyl, cycloalkylalkoxy, hydroxyalkyl, hydroxyalkoxy, alkoxyalkyl, alkoxyalkoxy, carboxyalkyl, carboxyalkoxy, alkoxycarbonylalkoxy, aryl, heteroaryl, benzyl, benzyloxy, 2-cyanoethoxy, 2,3-dihydroxypropoxy, 3,4-dihydroxybutoxy, -CH 2 R a, -CH 2 CH 2 R b, -(CH 2 ) n -C(O)O-R d, -(CH 2 ) n -N(R c )C(O)O-R d, -O-(CH 2 ) n -N(R c )C(O)O-R d, -(CH 2 ) n -R e or -O-(CH 2 ) n -R e; R a is cyano, acetylamino or N,N-dimethylamino; R b is cyano or carbamoyl; R c is H or methyl; R d is alkyl; R e is pyrrolidin-1-yl, piperidin-1-yl, piperidin-3-yl, morpholin-1-yl, 2-oxopyrrolidin-1-yl, 5-oxopyrrolidin-2-yl, 2,5-dioxopyrrolidin-1-yl, 2-oxoimidazolidin-1-yl, 4-(tert-butoxycarbonyl)piperazin-1-yl, 4-(aminomethyl)cyclohexyl or heteroaryl; R 4 is H or methyl; and to the salts of such compounds. These compounds are useful for the prevention or the treatment of bacterial infections.