21354-01-8

Usage

InChI:InChI=1/C8H8N2O2/c1-6(11)9-7-4-2-3-5-8(7)10-12/h2-5H,1H3,(H,9,11)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 34801-09-7 N-(2-aminophenyl)acetamide 
• 108-24-7 acetic anhydride 
• 88-74-4 2-nitro-aniline 
• 552-32-9 o-nitroacetanilide 

Downstream Products

• 1237-71-4 bis-(2-acetylamino-phenyl)-diazene-N-oxide 
• 117883-88-2 4-benzotriazol-2-yl-benzenesulfonic acid ; sodium-salt 
• 69395-27-3 2-Acetylamino-2'-(2-acetylaminophenylazo)stilben 
• 62189-02-0 2-acetamido-2''-amino-ortho-bisazobenzene 
• 13666-95-0 2,2'-diacetamido-ortho-azobenzene 
• 1346157-77-4 2-amino-2'-acetamido-tris-ortho-azobenzene 
• 1202564-22-4 2-acetamido-2-amino-ortho-bisazobenzene 
• 1346157-84-3 2-amino-ortho-bisazobenzene 
• 1346157-86-5 2-amino-2-nitro-ortho-bisazobenzene 
• 1346157-88-7 2-acetamido-2-nitro-ortho-bisazobenzene 
• 1346157-89-8 2-acetamido-ortho-bisazobenzene 
• 1346157-91-2 2-amino-tris-ortho-azobenzene 
• 1346157-92-3 2-nitro-tris-ortho-azobenzene 
• 1346157-95-6 2-acetamido-2'-nitro-tris-ortho-azobenzene 

Relevant academic research and scientific papers

Helical conformational dynamics and photoisomerism of alternating pyridinedicarboxamide/m-(phenylazo)azobenzene oligomers

Alternating sequences of pyridine-2,6-dicarboxamides and meta-(phenylazo)azobenzenes have been assembled into oligomers composed of four (8) and eight (9) azobenzene linkages. X-ray crystallography confirmed that oligomer 8 adopts a two-turn helical conformation with a helical pitch of approximately 3.4 A in the solid state. The presence of a two- and four-turn helical conformation of 8 and 9, respectively, in polar and nonpolar solvents was elucidated by the anisotropic upfield shifting of protons located within the helices, NOE enhancements between protons oriented toward the helix interior, and the diastereotopicity of the terminal benzyloxycarbonyl (CBz) methylene protons. 1H NMR line shape analysis of the CBz methylene hydrogens at the chain ends revealed a dynamic equilibria interconverting M and P helical conformations with energetic barriers (ΔG?) of 11.1 (ΔS? = -19.4 ± 1.6 cal mol-1 K-1; ΔH? = 6.5 ± 0.4 kcal/mol) for 8 and 13.8 kcal/mol (ΔS? = -6.6 ± 6.2 cal mol -1 K-1; ΔH? = 11.8 ± 1.8 kcal/mol) for 9. Irradiation of the oligomers with 350 nm light induces an E → Z isomerization of the azo linkages that decreases in efficacy at longer helix lengths. The suppression of E -Z isomerization is a consequence of the contrasting behavior of the azo linkages located at the helix termini, which afford ZIE ratios similar to those of model compound 7d, and the internal azo groups, which undergo significantly lower ZIEconversion ratios compared with 7e.

Azobenzene-diamides as Photopharmacological Ligands for Insect Ryanodine Receptor

Photoresponsive ligands are powerful tool compounds for studying receptor function with spatiotemporal resolution. However, to the best of our knowledge, such a ligand is not available for the ryanodine receptor (RyR). Herein, we present a photochromic ligand (PCL) for insect RyR by decorating chlorantraniliprole (CHL) with photoswitchable azobenzene (AB). We demonstrated that one potent ligand, named ABCHL13, shows light-induced reversible trans-cis isomerization and 3.5-fold insecticidal activity decrease toward oriental armyworm (Mythimna separata) after UV-light irradiation, that is, trans-ABCH13 has higher activity than the cis-ABCH13. ABCHL13 enables optical control over intracellular Ca2+ release in dorsal unpaired median (DUM) neurons of M. separata and American cockroach (Periplaneta americana) and cardiac function of P. americana. Our results provide a first photopharmacological toolkit that is applicable to light-dependent regulation of RyR and heart beating.

Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling

The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.

Synthesis and photochemical properties of oligo-ortho-azobenzenes

Azobenzenes have attracted great interest in recent years because of their ability to change conformation upon irradiation. This property has been featured in several applications not only in organic chemistry but also in biology. Even though monoazobenzenes have been extensively studied and documented in the literature, only a few methods are available for the synthesis of oligo-ortho-azobenzenes. Also, their photochemical properties have not been reported so far. This study shows an efficient strategy for the preparation of oligo-ortho-azobenzenes and the investigation of their photochemical properties. It is demonstrated that the absorption spectra are highly influenced by the substituents. Interestingly, none of the ortho-bis-, tris-, or tetra-azobenzenes showed any E → Z isomerization. Only the ortho-nitrogen-substituted monoazobenzenes' photochromic behavior upon UV irradiation was observed.

Synthesis and property studies of cyclotrisazobenzenes

Azobenzenophanes are fascinating macrocycles, which are of special interest due to their unique photochromic behavior. Cyclotrisazobenzenes 2 (R = H, Br, tBu) were prepared to probe how much strain the photoisomerization of the azobenzene motive can tolerate. The macrocycles were synthesized in an overall yield of 10-20% from oriho-phenylenediamine (6). Solid-state structures of cyclotrisazobenzenes 2a and 2b were obtained. Irradiation under various conditions did not induce any isomerization.