29882-73-3

Upstream product

• 100-34-5 benzene diazonium chloride 
• 586-96-9 Nitrosobenzene 
• 95-54-5 1,2-diamino-benzene 
• 98-95-3 nitrobenzene 
• 146651-75-4 tert–butyl (2–aminophenyl)carbamate 
• 62-53-3 aniline 

Downstream Products

• 1346157-87-6 2-nitro-ortho-bisazobenzene 
• 313485-89-1 N-phenyl-1H-benzo[d]imidazol-1-amine 
• 1916-72-9 2-phenyl-2H-1,2,3-benzotriazole 

Relevant academic research and scientific papers

Tuning of Bistability, Thermal Stability of the Metastable States, and Application Prospects in the C3-Symmetric Designs of Multiple Azo(hetero)arenes Systems

Light-responsive molecular systems with multiple photoswitches in C3-symmetric designs have enormous application potential. The design part of such molecular systems is critical due to its influence in several properties associated with the photoswitches. In order to tune, and in the evaluation of the design–property relationship, we synthesized 18 tripodal systems with variations in the core, linkers, connectivity, and azo(hetero)arene photoswitches. Through extensive spectroscopic and computational studies, we envisaged the factors controlling near-quantitative photoisomerization in both the directions (bistability) and the thermal stability of the metastable states. Furthermore, we also evaluated the impact of designs in obtaining reversible photo-responsive sol-gel phase transitions, solvatochromism, photo- and thermochromism.

Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions

Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.

Rational Remodeling of Atypical Scaffolds for the Design of Photoswitchable Cannabinoid Receptor Tools

Azobenzene-embedded photoswitchable ligands are the widely used chemical tools in photopharmacological studies. Current approaches to azobenzene introduction rely mainly on the isosteric replacement of typical azologable groups. However, atypical scaffolds may offer more opportunities for photoswitch remodeling, which are chemically in an overwhelming majority. Herein, we investigate the rational remodeling of atypical scaffolds for azobenzene introduction, as exemplified in the development of photoswitchable ligands for the cannabinoid receptor 2 (CB2). Based on the analysis of residue-type clusters surrounding the binding pocket, we conclude that among the three representative atypical arms of the CB2 antagonist, AM10257, the adamantyl arm is the most appropriate for azobenzene remodeling. The optimizing spacer length and attachment position revealed AzoLig 9 with excellent thermal bistability, decent photopharmacological switchability between its two configurations, and high subtype selectivity. This structure-guided approach gave new impetus in the extension of new chemical spaces for tool customization for increasingly diversified photo-pharmacological studies and beyond.

"TRPSWITCH" ? A STEP FUNCTION CHEMO-OPTOGENETIC LIGAND

Described herein are photoswitchable compounds that can activate TRPA1 channels in neuronal and non-neuronal cells. The TRPswitch molecules allow for optical control of both the activation and deactivation of TRPA1 channels. Such compounds can be used as research tools or therapeutics.

Azo aryl urea derivative, and preparation method and application thereof

The invention relates to an azo aryl urea derivative, and a preparation and an application thereof, and concretely discloses a compound represented by formula (I), or an optical isomer, a cis-trans-isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. Definitions of substituent groups in the general formula are described in the specification and claims. The invention further discloses a composition containing the above compound, and an application thereof. The compound has excellent anticancer activity on HepG2 liver cancer cells, MGC803 gastric cancer cells,HCT116 colon cancer and the like.

TRPswitch - A Step-Function Chemo-optogenetic Ligand for the Vertebrate TRPA1 Channel

Chemo-optogenetics has produced powerful tools for optical control of cell activity, but current tools suffer from a variety of limitations including low unitary conductance, the need to modify the target channel, or the inability to control both on and off switching. Using a zebrafish behavior-based screening strategy, we discovered "TRPswitch", a photoswitchable nonelectrophilic ligand scaffold for the transient receptor potential ankyrin 1 (TRPA1) channel. TRPA1 exhibits high unitary channel conductance, making it an ideal target for chemo-optogenetic tool development. Key molecular determinants for the activity of TRPswitch were elucidated and allowed for replacement of the TRPswitch azobenzene with a next-generation azoheteroarene. The TRPswitch compounds enable reversible, repeatable, and nearly quantitative light-induced activation and deactivation of the vertebrate TRPA1 channel with violet and green light, respectively. The utility of TRPswitch compounds was demonstrated in larval zebrafish hearts exogenously expressing zebrafish Trpa1b, where the heartbeat could be controlled using TRPswitch and light. Therefore, TRPA1/TRPswitch represents a novel step-function chemo-optogenetic system with a unique combination of high conductance, high efficiency, activity against an unmodified vertebrate channel, and capacity for bidirectional optical switching. This chemo-optogenetic system will be particularly applicable in systems where a large depolarization current is needed or sustained channel activation is desirable.

Azobenzene-benzoylphenylureas as photoswitchable chitin synthesis inhibitors

Benzoylphenylureas (BPUs) are used as synthetic insect growth regulators for inhibiting chitin synthesis. Merging insecticidal BPUs with photoswitchable azobenzene generated photoresponsive chitin synthesis inhibitors. A prepared azobenzene-benzoylphenylurea can be activated upon irradiation with UV light, and shows 6-fold and 2-fold activity difference to armyworm (Mythimna separata) and German cockroach (Blattella germanica) sulfonylurea receptors, respectively. This is the first example of a photoswitchable BPU insecticide. The generation of such a photoresponsive BPU insecticide allows for modulation of the insecticidal activity by light, and may facilitate the spatiotemporal control over the sulfonylurea receptor and the mechanistic study of this kind of insecticide.

Site-Selective C–H Amidation of Azobenzenes with Dioxazolones under Rhodium Catalysis

The rhodium(III)-catalyzed amidation reaction of azobenzenes with dioxazolones is described. This strategy allows the facile and efficient construction of highly substituted ortho-amidated azobenzenes by direct C–H cleavage approach. A wide range of substrates, excellent levels of chemoselectivity as well as high functional-group tolerance were observed. In addition, this protocol was used to generate an array of ortho-amidated ketazines. Further synthetic transformation of amidated azobenzenes furnished a facile construction of benzimidazole and benzotriazole derivatives.

Palladium-catalyzed direct ortho-nitration of azoarenes using NO2 as nitro source

A palladium-catalyzed direct ortho-nitration reaction of azoarenes was developed in which NO2 was used as both nitro source and oxidant for the first time. The nitration products were converted into o-aminoazoarenes or benzotriazole derivatives by a simple reduction.

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.