42794-41-2

Usage

InChI:InChI=1/C9H8BrNO4/c1-15-9(12)8(10)6-4-2-3-5-7(6)11(13)14/h2-5,8H,1H3

Upstream product

• 30095-98-8 methyl (2-nitrophenyl)acetate 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 67-56-1 methanol 

Downstream Products

• 50381-55-0 methyl α-phthalimido-2-nitrophenylacetate 
• 191984-23-3 (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid methoxycarbonyl-(2-nitro-phenyl)-methyl ester 
• 288591-67-3 N-(ethyl 2-nitrophenylglycine)nicotinamide 
• 288591-68-4 (2-nitro-phenyl)-[(pyridine-3-carbonyl)-amino]-acetic acid 
• 791050-91-4 ethyl (2-nitrophenyl)glycine 
• 50357-25-0 (+/-)-2-nitrophenylglycine hydrochloride 
• 72744-09-3 methyl 2-hydroxy-2-(2-nitrophenyl)acetate 

Relevant academic research and scientific papers

Formation of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones involving ring transformation of 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles

The reaction of 3-bromooxindole with substituted (hetero)aromatic thioamides in acetonitrile was studied. At room temperature the reaction preferably gives products of ring transformation i.e. 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles (3b-f,h) whereas at elevated temperature products of an Eschenmoser coupling reaction, i.e. 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones (2b-f), are formed exclusively. There exist only two exceptions (4-methoxy and 2-pyridinthioamide) in which the Eschenmoser coupling reaction always takes place giving 2a and 2g. Also N-methylation of the starting 3-bromooxindole completely prevents formation of thiazoles. The prepared thiazoles 3b-f are unstable in solution and they undergo slow ring transformation to 2b-f. The rate limiting step of this rearrangement involves cleavage of an intermediary thiirane ring, which is slowed down by electron-withdrawing substituents on the thioamide (ρ = ?1.15).

Enzymatic synthesis of caged NADP cofactors: Aqueous NADP photorelease and optical properties

The synthesis of caged NADP analogues 18, 19, and 20 has been accomplished by utilizing the transglycosidase activity of solubilized NAD glycohydrolase (porcine brain) to incorporate caged nicotinamides 2, 3, and 4 into NADP. The synthesis of several nicotinamides modified at the carboxamide with o-nitrobenzyl photolabile groups is demonstrated as well as their potential for enzymatic transglycosidation. These results further demonstrate the feasibility of direct enzymatic transglycosidation of sterically hindered substrates into NAD(P), although high nicotinamide analogue water solubility was found to be a necessary trait for yield enhancement with certain analogues. Caged analogues were surveyed under aqueous conditions for net NADP photorelease, while the UV and fluorescent properties of both analogues and their photobyproducts were assessed for compatibility with systems that rely on optical monitoring of enzyme activity. A highly water-soluble α-methyl-o-nitrobenzyl group 8 was developed for the synthesis of 20 in order to enhance net NADP photorelease. Compound 20 demonstrated a high 75% net NADP photoreleased without substantial UV optical blackening or fluorescent byproducts. Analogues 18 and 19 were shown by ESI/MALDI-MS to photogenerate primarily adducts of NADP with deleterious UV and fluorescent properties. Our work stresses the superior release properties conferred by α-methyl substitution on aqueous carboxamide photorelease from o-nitrobenzyl compounds.

Photolabile 'caged fatty acids containing a 1-(2'-nitrophenyl)-1,2-ethanediol moiety

1-(2'-Nitrophenyl)ethanediol was used to esterify the carboxylic acid function of fatty acids to prepare photosensitive fatty acid precursors for biological studies. The synthesis, photochemistry, and biological properties of several model cis-unsaturated fatty acids including arachidonic acid are described.

ANGIOTENSIN II ANTAGONISTS INCORPORATING A SUBSTITUTED PYRIDOIMIDAZOLYL RING

Substituted heterocycles attached through a methylene bridge to novel substituted phenyl derivatives of the Formula I are useful as angiotensin II antagonists. STR1