33488-29-8

Upstream product

• 10050-86-9 (4-dimethylamino-phenylimino)-phenyl-acetonitrile 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 95-54-5 1,2-diamino-benzene 
• 1124239-41-3 C₂₂H₂₇N₃ 
• 100-52-7 benzaldehyde 
• 21864-90-4 N-(tert-butyl)benzimidoyl cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 773837-37-9 sodium cyanide 
• 74144-28-8 Tetrazolo<1,5-a>chinoxalin 

Downstream Products

• 1124239-54-8 C₂₈H₂₇FN₄O 
• 1124239-59-3 C₃₃H₃₀N₄O₄ 
• 1124239-55-9 C₂₇H₂₆N₄O 
• 1124239-57-1 C₃₁H₃₄N₄O 

Relevant academic research and scientific papers

Anticancer properties of N-alkyl-2, 4-diphenylimidazo [1, 2-a] quinoxalin-1-amine derivatives; kinase inhibitors

Structure activity correlation revealed that the quinoxaline ring is a satisfactory backbone for anticancer activity and a specific functional group at position 1 and 2 can improve the activity. In this basis, besides quinoxaline, imidazoles as potential anticancer agents were used as a supplementary agents for cancer treatment. In this paper, a new series of N-alkyl-2, 4-diphenylimidazo [1, 2-a] quinoxalin-1-amine derivatives were synthesized in a simple and efficient step. The products are fully characterized by 1H NMR, 13C NMR, FT-IR, HRMS, and CHN elemental analysis. Several starting materials with different functionalities have been used for the synthesis of the final products with high isolated yields. The biological activities of the synthesized compounds were evaluated in kinase inhibition and cytotoxic activity in several cancerous cell lines. All compounds (6) were evaluated for inhibition of the cell proliferation using 4 cancerous cell lines. Five of the more active compounds were studied for determination of IC50%. Compounds 6(32–34) showed good activity on some of cancerous cell lines. The results showed that compound 6–32 has the highest biological activity (IC50% 9.77 for K562 cell line). An IC50% value of 15.84 μM was observed for 6–34. Furthermore 6–34 exhibited inhibition of ABL1 and c-Src kinases with an IC50% value of 5.25 μM and 3.94 μM respectively. Docking simulation was performed to position active synthesized compounds 6–32, 6–33, and 6–34 over the ABL1 active site in two different wild-type (DFG-in and DFG-out motif conformer) and T315I mutant to determine the probable binding orientation, conformation and mode of interaction. According to docking study, the docked location in wild type forms is similar and can be found near the P-loop region while in the case of T315I mutant form, the compounds have a distinct docked location which is close to the αC helix and activation loop. Also, it concluded the role of R1 substituent on phenyl ring produced higher interaction energy. Additionally, the detailed inter-molecular energy and types of non-bonding interaction of these compounds over the wild-type and mutant form of ABL1.

Palladium-Catalyzed Synthesis of α-Iminonitriles from Aryl Halides via Isocyanide Double Insertion Reaction

An efficient one-pot synthesis of α-iminonitriles from readily available aryl halides via palladium-catalyzed double isocyanide insertion and elimination has been developed, without using various hypertoxic cyanides and excess oxidants. Furthermore, the utility of this reaction was demonstrated by the rapid total synthesis of quinoxaline and the reaction of functional groups exchanged with aryl halides. (Chemical Equation Presented).

Synthesis of imidazo[1,2-a]quinoxalines by double Groebke reactions and inhibitory effects on radicals and DNA oxidation

The o-phenylenediamine, aldehyde, and 2,4,4-trimethylpentan-2-yl isocyanide performed a Groebke 3CR to afford 2-aminoquinoxaline, which can react with an aldehyde and t-butyl isocyanide via another Groebke 3CR to give imidazo[1,2-a]quinoxaline. Exchanging two aldehydes in the sequential Groebke 3CR led to a couple of imidazo[1,2-a]quinoxaline isomer, in which the aldehyde moiety located at 2- or 4-position. The ferrocenyl group at 4-position in imidazo[1,2-a]quinoxaline was found to be active in trapping galvinoxyl radical, while the phenolic hydroxyl group at 2-position played a synergistic role with 4-ferrocenyl or 4-flavonyl group in scavenging 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH). In addition, 4-ferrocenyl with N,N-dimethylaminophenyl group at 2-position was able to quench 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+[rad]). Moreover, the combination of 4-ferrocenyl with 2-phenyl group (bearing para-N,N-dimethylamino or hydroxyl group) exhibited high inhibitory effect on DNA oxidation induced by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH).

A reaction of 1,2-diamines and aldehydes with silyl cyanide as cyanide pronucleophile to access 2-aminopyrazines and 2-aminoquinoxalines

A new condensation reaction of ethylene-1,2-diamines or o-phenylenediamines and aromatic aldehydes with TMSCN as a cyanide-pronucleophile is documented. The reaction proceeds through a tandem sequence of desilylation, Strecker reaction, amidine-forming cy

Significant facilitation of metal-free aerobic oxidative cyclization of imines with water in synthesis of benzimidazoles

A simple, convenient, and environmentally benign protocol for the synthesis of benzimidazoles from ortho-phenylenediamines and aldehydes via aerobic oxidation was developed in wet organic solvents. Notably, water significantly accelerated this transformation, which allowed us to achieve this important transformation without the assistance of any metal catalysts and other co-oxidants. Mechanistic studies suggested that water acts as the nucleophilic catalyst for this transformation by the conversion of disfavored 5-endo-trig cyclization of imines to favored 5-exo-tet cyclization via tetrahedral intermediates and the subsequent aerobic oxidation of the resulting benzimidazolines affords benzimidazoles.

Synthesis of 2-aminoquinoxalines via one-pot cyanide-based sequential reaction under aerobic oxidation conditions

A highly efficient synthesis of 2-aminoquinoxalines has been developed via the one-pot two-step cyanide-mediated sequential reactions of ortho-phenylenediamines with aldehydes under aerobic oxidation conditions. A variety of substrates, including aliphati

Imidazo[l,2-a]quinoxalines accessed via two sequential isocyanide-based multicomponent reactions

A novel synthetic protocol toward imidazo[l,2-a]quinoxa-lines has been developed. It includes two isocyanide-based multicomponent reactions sequentially introducing four diversity elements to the final products

Substituted quinoxaline derivatives as interleukin-8 receptor antagonists

Quinoxaline compounds are described as well as methods for the preparation and pharmaceutical compositions of same, which are useful as interleukin-8 (IL-8) receptor antagonists and can be used in the treatment of a chemokine-mediated disease wherein the chemokine binds to an IL-8a (CXCR1) or b (CXCR2) receptor such as a chemokine-mediated disease selected from psoriasis, or atopic distress syndrome, arthritis, inflammatory bowel disease, Crohn's disease, ulcerative colitis, gastric ulcer, septic shock, endotoxic shock, gram-negative sepsis, toxic shock syndrome, stroke, cardiac and renal reperfusion injury, glomerulo-nephritis, or thrombosis, Alzheimer's disease, graft versus host reaction, allograft rejections, or allergic diseases.