29067-85-4Relevant articles and documents
[3+2] Cyclization of Azidotrimethylsilane with Quinoxalin-2(1H)-Ones to Synthesize Tetrazolo[1,5-a]quinoxalin-4(5H)-Ones
Yang, Qiming,Zhang, Yuecheng,Sun, Qian,Shang, Kun,Zhang, Hong-Yu,Zhao, Jiquan
, p. 4509 - 4514 (2018)
A convenient and efficient protocol for the synthesis of thetetrazolo[1,5-a]quinoxalin-4(5H)-ones via copper-catalyzed [3+2] cyclization of azidotrimethylsilane with quinoxalin-2(1H)-ones under mild conditions has been disclosed. This practical protocol is compatible with a variety of functional groups and provides an access to functionalized tetrazolo[1,5-a]quinoxalin-4(5H)-ones from readily available and safe starting materials. (Figure presented.).
Halting colorectal cancer metastasis via novel dual nanomolar MMP-9/MAO-A quinoxaline-based inhibitors; design, synthesis, and evaluation
Ayoup, Mohammed Salah,Abu-Serie, Marwa M.,Awad, Laila F.,Teleb, Mohamed,Ragab, Hanan M.,Amer, Adel
, (2021/06/14)
Matrix metalloproteinase-9 (MMP-9) and monoamine oxidase-A (MAO-A) are central signaling nodes in CRC and promotors of distant metastasis associated with high mortality rates. Novel series of quinoxaline-based dual MMP-9/MAO-A inhibitors were synthesized
A Synthetic Route Toward Tetrazoles: The Thermolysis of Geminal Diazides
Holzschneider, Kristina,Kirsch, Stefan F.,Mohr, Fabian,Tong, My Linh
, (2019/08/21)
A new synthetic route toward the tetrazole core is described, which is based on a general fragmentation pattern that was found in a range of compounds featuring geminal diazido units. Through a simple two-step procedure, the synthesis of structurally diverse target compounds containing a tetrazole, such as tetrazoloquinoxalinones, benzoylaryltetrazoles, tetrazolotriazinones, and tetrazoloazepinones, was easily accomplished, starting from broadly accessible substrates (i.e., oxindoles, diarylethanones, pyrazolones, and phenanthrols). The initial oxidative diazidation reaction with iodine and sodium azide under mild conditions is followed by the thermal fragmentation under microwave irradiation, leading to the tetrazole products. Noteworthy, an experimental solution is presented in which the potentially hazardous diazide intermediates are not isolated and the concentration of crude reaction mixtures containing diazides is not required to achieve the tetrazoles in good yields.
Synthesis of some 4-substituted hydrazinotetrazolo[1,5-a]quinoxalines
Deshmukh,Mali,Jadhav,Suryawanshi
, p. 1211 - 1213 (2008/09/18)
Reaction of 2,3 diketoquinoxaline in presence of phosphorus pentachloride and sodium azide in methanol gives 4-hydroxy tetrazolo[1,5-a]quinoxaline 3 which on reaction with phosphorous oxychloride gives 4-chloro tetrazolo[1,5-a] quinoxaline 4. This on treatment with hydrazine hydrate in ethanol yields 4-hydrazino tetrazolo[1,5-a]quinoxaline 5, which on reaction with various aldehydes in DMF gives 4-substituted hydrazinotetrazolo [1,5-a]quinoxalines 6a-g. The structures of compounds 6a-g have been confirmed by IR and 1H NMR.
Synthesis and excitatory amino acid pharmacology of a series of heterocyclic-fused quinoxalinones and quinazolinones
McQuaid,Smith,South,Mitch,Schoepp,True,Calligaro,O'Malley,Lodge,Ornstein
, p. 3319 - 3324 (2007/10/02)
As part of our program aimed at the development of potent excitatory amino acid antagonists, we synthesized and evaluated a series of substituted 1,2,4- triazolo[4,3-a]quinoxalin-4(5H)-ones, 4, tetrazolo[1,5-a]quinoxalin-4(5H)- ones, 5, and pyrazolo[1,5-c]quinazolin-5(6H)-ones, 6, and an imidazo[1,2- a]quinoxalin-4(5H)-one, 7. In general, the same heterocycles which demonstrated the best affinity for the AMPA receptor also demonstrated the best affinity for the glycine site on the NMDA receptor complex. 1-Propyl- 7,8-dichloro-1,2,4-triazolo[4,3-a]quinoxalin-4(5H)-one, 4d, was found to bind with the greatest affinity to the AMPA receptor with an IC50 of 0.83 μM and antagonized 40 μM AMPA-induced depolarization in the cortical slice preparation with an IC50 of 44 μM. 7,8-Dichloro-1,2,4-triazolo[4,3- a]quinoxalin-4(5H)-one, 4a, and 7,8-dichloroimidazo[1,2-a]quinoxalin-4(5H)- one, 7, possessed the best affinity for the glycine site with IC50 values of 0.63 and 1.26 μM, respectively. It is noteworthy that the SAR for the heterocyclic compounds did not directly parallel that of known quinoxalinediones (e.g. DNQX, 2, and DCQX, 15) at the AMPA receptor nor that of the kynurenic acids at the glycine site on the NMDA receptor complex.
