2379-56-8Relevant academic research and scientific papers
Synthesis of a Zn-salen resorcinarene-based cavitand and its fluorescence response to nitro compounds
Lee, Yujin,Koo, Hyo Geun,Jang, Seung Pyo,Erdmann, Alan B.,Vernetti, Samantha S.,Kim, Cheal,Harrison, Roger G.
, p. 245 - 250 (2014)
The synthesis, spectroscopic characterisation, conformational switching and fluorescence quenching efficiency of a resorcinarene-based cavitand containing Zn-salen (Zn-Cav) are reported. Synthesis of Zn-Cav was accomplished by the condensation of a quinoxaline derivatised with Zn-salen and a resorcinarene-based cavitand containing three quinoxalines. 1H NMR spectroscopy confirmed that in DMSO, chloroform and acetone Zn-Cav resides in the vase conformation. The molecular geometry of Zn-Cav selectively changes from vase to kite under acidic conditions. Detection by fluorescence quenching of nitro-containing molecules, such as 4-nitrotoluene, 2,4-dinitrotoluene and 2,3-dimethyl-2,3-dinitrobutane was explored by spectrofluorimetry. It was found that the fluorescence of Zn-Cav is efficiently quenched by nitroaromatic compounds.
Photochemically knocking out glutamate receptors in vivo
Chambers, James J.,Gouda, Hiroaki,Young, David M.,Kuntz, Irwin D.,England, Pamela M.
, p. 13886 - 13887 (2004)
AMPA (α-amino-3-hydroxy-5-methyl-4-isooxazole) receptors, a major subtype of ionotropic glutamate receptors (iGluRs), mediate the majority of the fast communication between neurons, and the activity-dependent trafficking of AMPA receptors at synapses plays a role in mammalian learning and memory. Here we describe the design, synthesis, and evaluation of a photoreactive AMPA receptor antagonist that provides a means of "knocking out" AMPA receptors present on the surface of cells. The antagonist, 6-azido-7-nitro-1,4-dihydroquinoxaline-2,3-dione (ANQX), was designed by introducing a photoreactive azido group onto a quinoxalinedione inhibitor scaffold. Computational docking of ANQX to the AMPA receptor ligand-binding core predicted efficient binding to AMPA receptors. Glutamate-evoked currents were reversibly blocked at micromolar ANQX concentrations prior to photolysis and irreversibly blocked following photolysis. ANQX provides a means of directly evaluating the trafficking of native AMPA receptors with unparalleled spatiotemporal resolution. Copyright
Synthesis of a visibly emissive 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine scaffold with large stokes shift and live cell imaging
Kanungo, Ajay,Patra, Dipendu,Mukherjee, Sanghamitra,Mahata, Tridib,Maulik, Prakas R.,Dutta, Sanjay
, p. 70958 - 70967 (2015)
We have developed a novel fluorescent scaffold 4 which is a 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine derivative from the reaction between di-tert-butyl but-2-ynedioate and a quinoxaline molecule containing a dimethyl amine side tail in high yield. The synthesis of scaffold 4 involves an sp3 C-N bond cleavage mechanism which is not very common. The scaffolds 4 is emissive in the visible range λem ～ (517-540) nm with large stokes shifts (5005-6378) cm-1 in ethanol. Laser confocal microscopy of the live HepG2 cells treated with compound 4f shows that it can be used for live cell imaging in nanomolar concentrations.
Novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and preparation and application thereof
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Paragraph 0178; 0180; 0192; 0203; 0222, (2021/08/19)
The invention provides a novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound as shown in a formula I, or a salt thereof, or a stereoisomer thereof. The compound is low in toxicity or basically non-toxic to normal cells, has an obvious inhibition effect to tumor cell lines, particularly has good lipid toxicity selectivity to tumor cells such as liver cancer, lung cancer and the like in vivo, and has an obvious inhibition effect; meanwhile, the compound can effectively activate SREBP1 and PPAR gamma, inhibit lipid transport MTTP, cause lipid aggregation in tumor cells and cause lipid toxicity of the tumor cells. The compound can be used for treating liver cancer, lung cancer and the like in a molecular targeting manner, is low in toxicity or even non-toxic, and has a good application prospect.
Facile synthesis and anti-proliferative activity evaluation of quinoxaline derivatives
Li, Zhulai,Lin, Jin,Wang, Jian,Wang, Panpan,Xu, Xiuzhi,Xue, Guozhen,Zha, Daijun,Zhang, Zemin
supporting information, (2020/01/31)
A series of “drug-like” compounds based on quinoxaline scaffold with arylsulfonyl hydrazinyl, arylformyl hydrazinyl or arylsulfonyl groups at C-2 and aryloxy groups at C-3, were synthesized in 4 or 5 steps involving cyclization, chlorination and coupling reactions. Cellular anti-proliferative activities of these quinoxaline derivatives in vitro were determined, which revealed that the inhibitory potency and selectivity of 6f was comparable to that of the positive control.
A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst
Zhang, Pei-Ming,Li, Yao-Wei,Zhou, Jing,Gan, Lin-Ling,Chen, Yong-Jie,Gan, Zong-Jie,Yu, Yu
, p. 1809 - 1814 (2018/07/25)
An efficient one-pot reaction has been developed for the synthesis of 2,3-dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o-phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3-dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds 3a–3h were characterized by IR, 1H-NMR, and mass spectroscopies. Compounds 3i–3n without spectroscopic data were characterized by IR, 1H-NMR, 13C-NMR, and mass spectroscopies.
A new solvent for the reaction of chlorination of hydroxyquinoxaline derivatives with vilsmeier reagent
Bouanane, Zohra,Bounekhel, Mahmoud,Elkolli, Meriem,Takfaoui, Abdelilah
, p. 903 - 906 (2018/04/09)
A new efficient procedure for the chlorination of hydroxyquinoxaline derivatives into the corresponding chlorides is described. It has been found that the use of 1-chlorobutane produces the highest yield, reduces the time of reaction and facilitates direct formation of crystals without any purification.
Rationalization of benzazole-2-carboxylate versus benzazine-3-one/ benzazine-2,3-dione selectivity switch during cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in aqueous medium
Dhameliya, Tejas M.,Chourasiya, Sumit S.,Mishra, Eshan,Jadhavar, Pradeep S.,Bharatam, Prasad V.,Chakraborti, Asit K.
, p. 10077 - 10091 (2018/05/31)
The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as ethyl glyoxalate and diethyl oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin's rule. On the other hand, the reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin's rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/ benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.
A new small molecule inhibitor of soluble guanylate cyclase
Mota, Filipa,Gane, Paul,Hampden-Smith, Kathryn,Allerston, Charles K.,Garthwaite, John,Selwood, David L.
, p. 5303 - 5310 (2015/11/11)
Soluble guanylate cyclase (sGC) is a haem containing enzyme that regulates cardiovascular homeostasis and multiple mechanisms in the central and peripheral nervous system. Commonly used inhibitors of sGC activity act through oxidation of the haem moiety, however they also bind haemoglobin and this limits their bioavailability for in vivo studies. We have discovered a new class of small molecule inhibitors of sGC and have characterised a compound designated D12 (compound 10) which binds to the catalytic domain of the enzyme with a KD of 11 μM in a SPR assay.
Design, synthesis and biological evaluation of type-II VEGFR-2 inhibitors based on quinoxaline scaffold
Shahin, Mai I.,Abou El Ella, Dalal A.,Ismail, Nasser S.M.,Abouzid, Khaled A.M.
, p. 16 - 26 (2014/06/24)
In an effort to develop ATP-competitive VEGFR-2 selective inhibitors, a series of new quinoxaline-based derivatives was designed and synthesized. The target compounds were biologically evaluated for their inhibitory activity against VEGFR-2. The design of the target compounds was accomplished after a profound study of the structure activity relationship (SAR) of type-II VEGFR-2 inhibitors. Among the synthesized compounds, 1-(2-((4-methoxyphenyl)amino)-3- oxo-3,4 dihydroquinoxalin-6-yl)-3-phenylurea (VIIa) displayed the highest inhibitory activity against VEGFR-2. Molecular modeling study involving molecular docking and field alignment was implemented to interpret the variable inhibitory activity of the newly synthesized compounds.
