1128-90-1

Usage

Uses

Used in Organic Synthesis:
3-nitro-8-selena-7,9-diazabicyclo[4.3.0]nona-2,4,6,9-tetraene is used as a synthetic intermediate for the creation of various organic compounds. Its unique structure and reactivity make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 3-nitro-8-selena-7,9-diazabicyclo[4.3.0]nona-2,4,6,9-tetraene is utilized as a key component in the development of new drugs. Its structural features and potential reactivity can be harnessed to design and synthesize novel therapeutic agents with improved efficacy and selectivity.
Used in Materials Science:
3-nitro-8-selena-7,9-diazabicyclo[4.3.0]nona-2,4,6,9-tetraene is employed as a precursor in the development of advanced materials with specific properties. Its incorporation into materials can lead to new functionalities, such as improved conductivity, catalytic activity, or sensing capabilities.
Further research and exploration of the properties and potential applications of 3-nitro-8-selena-7,9-diazabicyclo[4.3.0]nona-2,4,6,9-tetraene are necessary to fully understand its capabilities and limitations, paving the way for its broader utilization in various industries.

InChI:InChI=1/C6H3N3O2Se/c10-9(11)4-1-2-5-6(3-4)8-12-7-5/h1-3H

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 

Downstream Products

• 1360067-55-5 7-benzyl-8-methyl-6-phenyl-7H-[1,2,5]selenadiazolo[3,4-e]isoindole 
• 1360067-58-8 7-benzyl-6-methyl-8-phenyl-7H-[1,2,5]selenadiazolo[3,4-e]isoindole 

Relevant academic research and scientific papers

A new facet of the reaction of nitro heteroaromatic compounds with ethyl isocyanoacetate

Nitro heteroarenes react with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5.4.0]undecene (DBU) to give pyrroles or pyrimidine N-oxide depending on the structure of the starting nitro compounds. For example, 4-nitro-2,1,3-benzothiadiazole 3a reacted with ethyl isocyanoacetate to give ethyl 2,1,3-benzothiadiazolo[3,4-c]pyrrole-2-carboxylate 4a (33%), while a similar reaction with 5-nitro-2,1,3-benzothiadiazole 3b gave the corresponding compound 4b (21%) as a sole product. A plausible mechanism for these reactions is presented.

Chromatographic determination of total selenium in biofortified allium sp. Following piazselenol formation and micro-solid-phase extraction

Herein, a method based on selective piazselenol formation is applied for total selenium determination in biofortified Allium species. Piazselenol is formed by reacting Se(IV) with an aromatic diamine, namely 4-nitro-1,2-phenylenediamine, in acidic medium. Samples were digested in a nitric acid/hydrogen peroxide open system, followed by selenate reduction in hydrochloric acid. Reaction conditions were optimized in terms of pH, temperature, reaction time, and other auxiliary reagents for interference removal, namely, EDTA and hydroxylamine. For the extraction of the selectively formed 4-nitro-piazselenol, micro-solid-phase extraction (μSPE) was applied, and the analysis and detection of the corresponding complex was performed by HPLC coupled with DAD. An external standard calibration curve was developed (R2 = 0.9994) with good sensitivity, and was used to calculate the total selenium content from several Allium plants material, with good intermediate precision (RSD% 16%). The accuracy of the method was evaluated using both, a comparison with an accepted reference method from our previously published data, as well as three certified reference material with recoveries between 84–126%. The limit of detection was determined to be 0.35 μg/g (in solids) and 1.1 μg/L (in solution), while the limit of quantification was 1.07 μg/g and 3.4 μg/L (in solution). Using the proposed method, selenium content can be quickly and accurately determined in several types of samples. In addition, this study present experimental conditions for overcoming the interferences that might be encountered in selenium determination using piazselenol.

Selenadiazole derivatives as theranostic agents for simultaneous cancer chemo-/radiotherapy by targeting thioredoxin reductase

The lack of early and timely diagnosis of tumors and the monitoring of their response to therapeutics have limited the successful cancer treatments. Theranostic agents are expected to realize the dual-purpose of simultaneous diagnosis and therapy for treatments of cancers. In the present study, we have examined the effects of the chemical structure of selenadiazole derivatives (SeDs) on their anticancer efficacy and radio-sensitization against clinically used X-rays. The results showed that the introduction of a nitro group (-NO2) into SeD-3 significantly enhanced the anticancer activity of SeDs. The higher lipophilicity endowed SeD-3 with higher cellular internalization ability, resulting in higher cellular uptake and anticancer efficacy. Specifically, the capacity of autofluorescence allowed the use of SeD-3 as a promising theranostic agent to directly monitor the cellular uptake, localization and biodistribution in vitro and in vivo. Interestingly, SeD-3 also significantly enhanced the sensitivity of HeLa cervical cells to X-ray-induced apoptosis by targeting the inhibition of TrxR and promoting intracellular ROS overproduction, which activated the downstream ROS-mediated signaling pathways to regulate cell apoptosis. Furthermore, SeD-3 exhibited satisfactory in vivo antitumor efficacy through the inhibition of tumor proliferation and induction of tumor cell apoptosis, and showed no toxicity to the main organs. Moreover, from the results of hematological analysis, we found that not only inhibiting the tumor growth, treatment of SeD-3 also alleviated the damage of liver, kidney and heart function of nude mice induced by HeLa xenografts. Taken together, this study demonstrates that SeDs could be further developed as an effective and safe theranostic agent for simultaneous cancer chemo-/radiotherapy.