59194-26-2Relevant academic research and scientific papers
Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement
Li, Shichen,Feng, Lei,Ma, Chen
, p. 9320 - 9323 (2021/06/14)
A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.
Terminal methyl as a one-carbon synthon: Synthesis of quinoxaline derivatives: Via radical-type transformation
Wang, Xinfeng,Liu, Huanhuan,Xie, Caixia,Zhou, Feiyu,Ma, Chen
supporting information, p. 2465 - 2470 (2020/02/20)
An iron-promoted method for the construction of pyrrolo[1,2-a]quinoxaline derivatives has been developed. Ferric chloride served as a promoter and as a Lewis acid in the reaction. Solvents provided the corresponding carbon sources simultaneously. The majority of solvents with terminal methyl groups, including ethers, amines and dimethyl sulfoxide, were reactive in the synthesis of quinoxaline derivatives at a certain yield via C-H(sp3) amination/C-O or C-N (C-S) cleavage. This method was applicable to a wide range of pyrrolo[1,2-a]quinoxaline and indolo[1,2-a]quinazoline substrates.
KI-Mediated One-Pot Transition-Metal-Rree Synthesis of 4-Phenylpyrrolo[1,2-a]quinoxalines
Li, Shichen,Xie, Caixia,Chu, Xianglong,Dai, Zhen,Feng, Lei,Ma, Chen
supporting information, p. 4950 - 4956 (2020/08/10)
An efficient and eco-friendly method for the synthesis of pyrrolo[1,2-a]quinoxalines is presented. Compared to previous methods, this protocol is transition-metal-free and only potassium iodide is required. A series of substituted 4-phenylpyrrolo[1,2-a]quinoxalines are obtained in moderate to good yields.
Pyrrolo[1,2-a]quinoxalines: Insulin Mimetics that Exhibit Potent and Selective Inhibition against Protein Tyrosine Phosphatase 1B
García-Marín, Javier,Griera, Mercedes,Sánchez-Alonso, Patricia,Di Geronimo, Bruno,Mendicuti, Francisco,Rodríguez-Puyol, Manuel,Alajarín, Ramón,de Pascual-Teresa, Beatriz,Vaquero, Juan J.,Rodríguez-Puyol, Diego
, p. 1788 - 1801 (2020/09/15)
PTP1B dephosphorylates insulin receptor and substrates to modulate glucose metabolism. This enzyme is a validated therapeutic target for type 2 diabetes, but no current drug candidates have completed clinical trials. Pyrrolo[1,2-a]quinoxalines substituted at positions C1–C4 and/or C7–C8 were found to be nontoxic to cells and good inhibitors in the low- to sub-micromolar range, with the 4-benzyl derivative being the most potent inhibitor (0.24 μm). Some analogues bearing chlorine atoms at C7 and/or C8 kept potency and showed good selectivity compared to TCPTP (selectivity index '40). The most potent inhibitors behaved as insulin mimetics by increasing glucose uptake. The 4-benzyl derivative inhibited insulin receptor substrate 1 and AKT phosphorylation. Molecular docking and molecular dynamics simulations supported a putative binding mode for these compounds to the allosteric α3/α6/α7 pocket, but inconsistent results in enzyme inhibition kinetics were obtained due to the high tendency of these inhibitors to form stable aggregates. Computational calculations supported the druggability of inhibitors.
Catalyst-Controlled Chemodivergent Annulation to Indolo/Pyrrolo-Fused Diazepine and Quinoxaline
Dhole, Sandip,Chiu, Wei-Jung,Sun, Chung-Ming
, p. 2916 - 2925 (2019/04/26)
Catalyst-controlled chemodivergent annulation between o-indolo anilines and diazo compounds has explored for the synthesis of indolo-fused diazepine and quinoxaline. Under the Rh(III) catalyst, reaction proceeded through the free amine assisted C2?H activation followed by amidation leading to the diazepino[1,7-a]indole in a highly selective manner. While with Ru(II) catalyst, reaction involves formation Ru?carbene complex followed by ?NH2 group insertion and cascade cyclization via metallo-ene type reaction, β-hydride elimination to furnish the indolo[1,2-a]quinoxaline as the predominating product. This strategy directs modular approach towards the construction of unique indolo-fused diazepine/quinoxaline as well as pyrrolo-fused diazepine/quinoxaline scaffolds in excellent yields. (Figure presented.).
Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives
Xie, Caixia,Zhang, Zeyuan,Li, Danyang,Gong, Jian,Han, Xushuang,Liu, Xuan,Ma, Chen
, p. 3491 - 3499 (2017/04/11)
An efficient, green, and novel method for the synthesis of N-heterocycle-fused quinoxalines is reported herein. Dimethyl sulfoxide was used as both a reactant and a solvent in this reaction. A wide range of products in moderate to excellent yields were obtained, including pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, 1H-pyrrolo[3,2-c]quinolines, and benzo[4,5]imidazo[1,2-c]quinazolines.
Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-: A] quinoxalines
Liu, Huanhuan,Zhou, Feiyu,Luo, Wen,Chen, Yuxin,Zhang, Chenyang,Ma, Chen
, p. 7157 - 7164 (2017/09/07)
A practical and concise protocol for the efficient synthesis of pyrrolo[1,2-a]quinoxalines from readily available α-amino acids and 2-(1H-pyrrol-1-yl)anilines under transition metal-free conditions has been established. This protocol, which includes the formation of new C-C and C-N bonds, features a wide substrate scope with a broad range of functional group tolerance.
SMALL MOLECULES INHIBITORS OF RAD51
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, (2017/09/15)
Embodiments concern methods and small molecule compositions for selectively inhibiting RAD51-mediated D-loop formation while preserving RAD51's ability to form nucleoprotein filaments. The selective RAD51 D-loop formation activity inhibitors DNA repair while minimizing replication-associated toxicity in normal tissue.
Design, synthesis and antimalarial activity of novel bis{N-[(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]-3-aminopropyl}amine derivatives
Guillon, Jean,Cohen, Anita,Gueddouda, Nassima Meriem,Das, Rabindra Nath,Moreau, Stéphane,Ronga, Luisa,Savrimoutou, Solène,Basmaciyan, Louise,Monnier, Alix,Monget, Myriam,Rubio, Sandra,Garnerin, Timothée,Azas, Nadine,Mergny, Jean-Louis,Mullié, Catherine,Sonnet, Pascal
, p. 547 - 563 (2017/11/10)
Novel series of bis- and tris-pyrrolo[1,2-a]quinoxaline derivatives 1 were synthesized and tested for in vitro activity upon the intraerythrocytic stage of W2 and 3D7 Plasmodium falciparum strains. Biological results showed good antimalarial activity with IC50 in the μM range. In attempting to investigate the large broad-spectrum antiprotozoal activities of these new derivatives, their properties toward Leishmania donovani were also investigated and revealed their selective antiplasmodial profile. In parallel, the in vitro cytotoxicity of these molecules was assessed on the human HepG2 cell line. Structure–activity relationships of these new synthetic compounds are discussed here. The bis-pyrrolo[1,2-a]quinoxalines 1n and 1p were identified as the most potent antimalarial candidates with selectivity index (SI) of 40.6 on W2 strain, and 39.25 on 3D7 strain, respectively. As the telomeres of the parasite could constitute an attractive target, we investigated the possibility of targeting Plasmodium telomeres by stabilizing the Plasmodium telomeric G-quadruplexes through a FRET melting assay by our new compounds.
Development of Small Molecules that Specifically Inhibit the D-loop Activity of RAD51
Lv, Wei,Budke, Brian,Pawlowski, Michal,Connell, Philip P.,Kozikowski, Alan P.
, p. 4511 - 4525 (2016/06/13)
RAD51 is the central protein in homologous recombination (HR) DNA repair and represents a therapeutic target in oncology. Herein we report a novel class of RAD51 inhibitors that were identified by high throughput screening. In contrast to many previously
