28096-58-4

Upstream product

• 700-37-8 4-chloro-2-fluoro-nitrobenzene 
• 108-91-8 cyclohexylamine 
• 610-40-2 3,4-dinitro-chlorobenzene 

Downstream Products

• 79759-04-9 N¹-cyclohexyl-5-chloro-o.phenylenediamine 
• 914401-69-7 C₂₀H₂₀ClN₃O₂ 
• 79759-19-6 (4-Chloro-2-cyclohexylamino-phenyl)-carbamic acid ethyl ester 
• 79759-65-2 5-Chloro-3-cyclohexyl-1-methyl-1,3-dihydro-benzoimidazol-2-one 
• 79759-64-1 5-chloro-3-cyclohexyl-1,3-dihydro-2H-benzimidazol-2-one 
• 1027376-22-2 N²-Cyclohexyl-4-imidazol-1-yl-benzene-1,2-diamine 
• 181869-94-3 N-cyclohexyl-5-(1H-imidazol-1-yl)-2-nitroaniline 

Relevant academic research and scientific papers

Novel AMPA receptor antagonists: Synthesis and structure-activity relationships of 1-hydroxy-7-(1H-imidazol-1-yl)-6-nitro-2,3(1H,4H)- quinoxalinedione and related compounds

As part of our study of novel antagonists at the α-amino-3-hydroxy-5- methylisoxazole-4-propionate (AMPA) subtype of excitatory amino acid (EAA) receptors and the pharmacophoric requirements of the receptor, we designed and synthesized a series of 1-substituted 6-imidazolyl-7-nitro-, and 7- imidazolyl-6-nitroquinoxalinediones, as well as related compounds, 6a-j, 7, 11a-e, 15, and 17, which are 1- and 4-substituted analogues of 1 (YM90K), and evaluated their activity to inhibit [3H]AMPA binding from rat whole brain. On the basis of their structure-activity relationships (SAR), we deduced that the amide proton of the imidazolyl-near side of the quinoxalinedione nucleus is not essential for AMPA receptor binding, whereas that of the imidazolyl- far amide is. Further, the receptors possess size-limited bulk tolerance for their N-substituents on the imidazolyl-near amide portion. Moreover, we found that introduction of a hydroxyl group at the imidazolyl-near amide portion causes a severalfold improvement in AMPA receptor affinity over unsubstituted derivatives. Among the compounds, 1-hydroxy-7-(1H-imidazol-1-yl)-6-nitro- 2,3(1H,4H)-quinoxalinedione (11a) showed high affinity for AMPA receptor with a K(i) value of 0.021 μM, which is severalfold greater than that of 1 and NBQX (2) (1, K(i) = 0.084 μM; 2, K(i) = 0.060 μM). Compound 11a also showed over 100-fold selectivity for the AMPA receptor than for the N-methy]-D- aspartate (NMDA) receptor and the glycine site on NMDA receptor.

Cycloalkyl or benzyl-6-substituted-quinoxalinediones

Heterocyclic dihydroxyquinoxaline compounds having the formula STR1 wherein R 1 is C 1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C 3-8 -cycloalkyl, aryl, aralkyl; and wherein R 6 is, hydrogen, halogen, CN, CF 3, NO 2, or OR'', wherein R'' is C 1-4 -alkyl and R 5, R 7 and R 8 is hydrogen, provided R 6 is not CF 3, OCH 3, NO 2, C 1 or Br when R 1 is CH 3 ; orR 6 and R 7 independently are NO 2, halogen, CN, CF 3, or OR'', wherein R'' is C 1-4 -alkyl, and R 5 and R 8 are each hydrogen; orR 5 and R 6 together form a further fused aromatic ring, which may be substituted with halogen, NO 2, CN, CF 3 or OR'', wherein R'' is C 1-4 -alkyl, and R 7 and R 8 independently are hydrogen, halogen, CN, CF 3, NO 2 or OR'', wherein R'' is C 1-4 -alkyl; orR 7 and R 8 together form a further fused aromatic ring, which may be substituted with halogen, NO 2, CN, CF 3 or OR'', wherein R'' is C 1-4 -alkyl, and R 5 and R 6 independently are hydrogen, halogen, CN, CF 3, NO 2 or OR'', wherein R'' is C 1-4 -alkyl.The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use.The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters, particularly the quisqualate receptors, and especially as neuroleptics.