51343-11-4

Upstream product

• 615-43-0 2-iodophenylamine 
• 586-96-9 Nitrosobenzene 
• 17082-12-1 trans-azobenzene 
• 62-53-3 aniline 
• 1227476-15-4 Azobenzene 

Downstream Products

• 137720-91-3 1-(2-iodophenyl)-2-phenylhydrazine 
• 713527-94-7 (E)-allyldiethoxy[2-(phenylazo)phenyl]silane 
• 203128-22-7 [2-(phenylazo)phenyl-C,N']tellurenyl iodide 
• 1019-13-2 3-amino-2-phenyl-2H-indazole 
• 38302-59-9 2-(phenylazo-1-yl)benzonitrile 

Relevant academic research and scientific papers

Reversible Photoswitchable Inhibitors Generate Ultrasensitivity in Out-of-Equilibrium Enzymatic Reactions

Ultrasensitivity is a ubiquitous emergent property of biochemical reaction networks. The design and construction of synthetic reaction networks exhibiting ultrasensitivity has been challenging, but would greatly expand the potential properties of life-like materials. Herein, we exploit a general and modular strategy to reversibly regulate the activity of enzymes using light and show how ultrasensitivity arises in simple out-of-equilibrium enzymatic systems upon incorporation of reversible photoswitchable inhibitors (PIs). Utilizing a chromophore/warhead strategy, PIs of the protease α-chymotrypsin were synthesized, which led to the discovery of inhibitors with large differences in inhibition constants (Ki) for the different photoisomers. A microfluidic flow setup was used to study enzymatic reactions under out-of-equilibrium conditions by continuous addition and removal of reagents. Upon irradiation of the continuously stirred tank reactor with different light pulse sequences, i.e., varying the pulse duration or frequency of UV and blue light irradiation, reversible switching between photoisomers resulted in ultrasensitive responses in enzymatic activity as well as frequency filtering of input signals. This general and modular strategy enables reversible and tunable control over the kinetic rates of individual enzyme-catalyzed reactions and makes a programmable linkage of enzymes to a wide range of network topologies feasible.

Active ester functionalized azobenzenes as versatile building blocks

Azobenzenes are important molecular switches that can still be difficult to functionalize selectively. A high yielding Pd-catalyzed cross-coupling method under mild conditions for the introduction of NHS esters to azobenzenes and diazocines has been established. Yields were consistently high with very few exceptions. The NHS functionalized azobenzenes react with primary amines quantitatively. These amines are ubiquitous in biological systems and in material science.

Rh(iii)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide

A new approach for highly regioselective iodination of azobenzenes with alkyl iodide as the iodinating reagent enabled by Rh-catalyzed oxidative C-H activation has been developed. By changing the oxidant, various mono- and di-iodinated azobenzenes were smoothly obtained in moderate to excellent yields, respectively. The preliminary mechanistic study reveals that the reaction process might undergo electrophilic substitution of the directed ortho metalated five-membered rhodacycle compound by an iodine cationic species generated in situ from alkyl iodide and oxidant.

Pd/Cu cooperative catalysis: an efficient synthesis of (3-isoindazolyl)allenes via cross-coupling of 2-alkynyl azobenzenes and terminal alkynes

An efficient synthesis of (3-isoindazolyl)allenes from 2-alkynyl azobenzenes and terminal alkynes via cooperative Pd(PPh3)2Cl2/CuI-catalyzed cross-coupling has been developed. By making use of this approach, (3-isoindazoly

Cu/Pd cooperatively catalyzed tandem C-N and C-P bond formation: Access to phosphorated 2: H -indazoles

A novel Cu/Pd cooperatively catalyzed tandem C-N and C-P bond formation reaction between 2-alkynyl azobenzenes and P(O)H compounds has been developed. This reaction provides a convenient approach for the synthesis of various phosphorated 2H-indazoles in m

Modular Synthetic Route to Monofunctionalized Porphyrin Architectures

The synthesis of a borylated Ni2+ porphyrin and its application as a versatile precursor for building up functional ortho-substituted tetraaryl porphyrin architectures is reported. This precursor porphyrin provides the basis for efficient modul

High-Yield Lithiation of Azobenzenes by Tin-Lithium Exchange

The lithiation of halogenated azobenzenes by halogen-lithium exchange commonly leads to substantial degradation of the azo group to give hydrazine derivatives besides the desired aryl lithium species. Yields of quenching reactions with electrophiles are therefore low. This work shows that a transmetalation reaction of easily accessible stannylated azobenzenes with methyllithium leads to a near-quantitative lithiation of azobenzenes in para, meta, and ortho positions. To investigate the scope of the reaction, various lithiated azobenzenes were quenched with a variety of electrophiles. Furthermore, mechanistic 119Sn NMR spectroscopic studies on the formation of lithiated azobenzenes are presented. A tin ate complex of the azobenzene was detected and characterized at low temperature.

Copper-catalyzed cascade cyclization reaction of 2-haloaryltriazenes and sodium azide: Selective synthesis of 2 H-benzotriazoles in water

A new approach to the synthesis of 2 H-benzotriazoles is described. This strategy is based on the copper-catalyzed Ci￡N coupling of 2-haloaryltriazenes or 2-haloazo compounds with sodium azide and the intramolecular addition of nitrene to N=N bonds. This approach allows the synthesis of various N-amino- and N-aryl-2 H-benzotriazoles in water, in good to excellent yields. The procedure is simple and the starting materials and catalyst are easily available, offering a practical and convenient synthetic route to 2-substituted benzotriazoles.

THIAZOLYL AND OXAZOLYL UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS

Compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis or pelvic pain syndrome.

N-(MONOCYCLIC ARYL),N'-PYRAZOLYL-UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS

Compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis or pelvic pain syndrome.