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Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene
Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline via oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di-t-butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde in situ. Oxygen played a crucial role in the oxidation process to accelerate benzaldehyde formation. Subsequent Pictet-Spengler-type annulation completed the quinoxaline structure. The protocol tolerated various kinds of functional groups and provided 22 4-aryl pyrrolo[1,2-α]quinoxalines when various methyl arene derivatives were used. The developed method proceeded in air, and all catalysts, reagents, and solvents were easily accessible.
Ahn, Jiwon,Lee, Seok Beom,Song, Injae,Chun, Simin,Oh, Dong-Chan,Hong, Suckchang
p. 7390 - 7402
(2021/06/21)

Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement
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.
Li, Shichen,Feng, Lei,Ma, Chen
supporting information
p. 9320 - 9323
(2021/06/14)

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions
A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is
Ding, Chengcheng,Feng, Kaili,Li, Shichen,Ma, Chen
supporting information
p. 5542 - 5548
(2021/08/16)

Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(iii) catalysis
Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO3 or CO2. Furthermore, some control experiments are conducted to elucidate the reaction mechanism. This journal is
Hu, Fang-Peng,Zhang, Xue-Guo,Wang, Meng,Wang, He-Song,Huang, Guo-Sheng
supporting information
p. 11980 - 11983
(2021/12/01)

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
p. 16848 - 16857
(2021/12/06)

Pyrrolo[1,2-a]quinoxalines: Insulin Mimetics that Exhibit Potent and Selective Inhibition against Protein Tyrosine Phosphatase 1B
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.
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
supporting information
p. 1788 - 1801
(2020/09/15)

Synthesis of new piperazinyl-pyrrolo[1,2-: A] quinoxaline derivatives as inhibitors of Candida albicans multidrug transporters by a Buchwald-Hartwig cross-coupling reaction
Two series of piperazinyl-pyrrolo[1,2-a]quinoxaline derivatives were prepared via a Buchwald-Hartwig cross-coupling reaction and then evaluated for their ability to inhibit the drug efflux activity of CaCdr1p and CaMdr1p transporters of Candida albicans overexpressed in a Saccharomyces cerevisiae strain. In the initial screening of twenty-nine piperazinyl-pyrrolo[1,2-a]quinoxaline derivatives, twenty-three compounds behaved as dual inhibitors of CaCdr1p and CaMdr1p. Only four compounds showed exclusive inhibition of CaCdr1p or CaMdr1p. Further biological investigations were developed and for example, their antifungal potential was evaluated by measuring the growth of control yeast cells (AD1-8u-) and efflux pump-overexpressing cells (AD-CDR1 and AD-MDR1) after exposition to variable concentrations of the tested compounds. The MIC80 values of nineteen compounds ranging from 100 to 901 μM for AD-CDR1 demonstrated that relative resistance index (RI) values were between 8 and 274. In comparison, only seven compounds had RI values superior to 4 in cells overexpressing Mdr1p. These results indicated substrate behavior for nineteen compounds for CaCdr1p and seven compounds for CaMdr1p, as these compounds were transported via MDR transporter overexpressing cells and not by the AD1-8u- cells. Finally, in a combination assay with fluconazole, two compounds (1d and 1f) have shown a synergistic effect (fractional inhibitory concentration index (FICI) values ≤ 0.5) at micromolar concentrations in the AD-MDR1 yeast strain overexpressing CaMdr1p-protein, indicating an excellent potency toward chemosensitization.
Guillon, Jean,Nim, Shweta,Moreau, Stéphane,Ronga, Luisa,Savrimoutou, Solène,Thivet, Elisabeth,Marchivie, Mathieu,Di Pietro, Attilio,Prasad, Rajendra,Le Borgne, Marc
p. 2915 - 2931
(2020/02/03)

Visible-Light-Driven Difluoromethylation of Isocyanides with S-(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines
A highly efficient approach of visible-light-driven radical difluoromethylation of isocyanides to access a wide variety of difluoromethylated phenanthridines and isoquinolines is herein described. Electrophilic S-(difluoromethyl)diarylsulfonium salt proved to be a good difluoromethyl radical precursor under photoredox catalysis. A broad range of isocyanides were tolerated to furnish the corresponding difluoromethylated phenanthridines, isoquinolines, furo[3,2-c]pyridine, and pyrido[3,4-b]indole in moderate to excellent yields under mild conditions. A plausible mechanism was also proposed.
Chen, Jia-Yi,Li, Xin,Lin, Li-Ting,Liu, Guo-Kai,Qin, Wen-Bing,Wong, Henry N. C.,Xiong, Wei
p. 10479 - 10487
(2020/09/23)

Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst
A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.
Ryabchuk, Pavel,Leischner, Thomas,Kreyenschulte, Carsten,Spannenberg, Anke,Junge, Kathrin,Beller, Matthias
supporting information
p. 18679 - 18685
(2020/09/02)

Terminal methyl as a one-carbon synthon: Synthesis of quinoxaline derivatives: Via radical-type transformation
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.
Wang, Xinfeng,Liu, Huanhuan,Xie, Caixia,Zhou, Feiyu,Ma, Chen
supporting information
p. 2465 - 2470
(2020/02/20)

KI-Mediated One-Pot Transition-Metal-Rree Synthesis of 4-Phenylpyrrolo[1,2-a]quinoxalines
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.
Li, Shichen,Xie, Caixia,Chu, Xianglong,Dai, Zhen,Feng, Lei,Ma, Chen
supporting information
p. 4950 - 4956
(2020/08/10)

Optimization of Drug Candidates That Inhibit the D-Loop Activity of RAD51
RAD51 is the central protein in homologous recombination (HR) repair, where it first binds ssDNA and then catalyzes strand invasion via a D-loop intermediate. Additionally, RAD51 plays a role in faithful DNA replication by protecting stalled replication forks; this requires RAD51 to bind DNA but may not require the strand invasion activity of RAD51. We previously described a small-molecule inhibitor of RAD51 named RI(dl)-2 (RAD51 inhibitor of D-loop formation #2, hereafter called 2 h), which inhibits D-loop activity while sparing ssDNA binding. However, 2 h is limited in its ability to inhibit HR in vivo, preventing only about 50 % of total HR events in cells. We sought to improve upon this by performing a structure–activity relationship (SAR) campaign for more potent analogues of 2 h. Most compounds were prepared from 1-(2-aminophenyl)pyrroles by forming the quinoxaline moiety either by condensation with aldehydes, then dehydrogenation of the resulting 4,5-dihydro intermediates, or by condensation with N,N′-carbonyldiimidazole, chlorination, and installation of the 4-substituent through Suzuki–Miyaura coupling. Many analogues exhibited enhanced activity against human RAD51, but in several of these compounds the increased inhibition was due to the introduction of dsDNA intercalation activity. We developed a sensitive assay to measure dsDNA intercalation, and identified two analogues of 2 h that promote complete HR inhibition in cells while exerting minimal intercalation activity.
Budke, Brian,Tueckmantel, Werner,Miles, Kelsey,Kozikowski, Alan P.,Connell, Philip P.
supporting information
p. 1031 - 1040
(2019/04/30)

Catalyst-Controlled Chemodivergent Annulation to Indolo/Pyrrolo-Fused Diazepine and Quinoxaline
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.).
Dhole, Sandip,Chiu, Wei-Jung,Sun, Chung-Ming
supporting information
p. 2916 - 2925
(2019/04/26)

NBE-Controlled Palladium-Catalyzed Interannular Selective C-H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2-Acetamides
A novel palladium-catalyzed interannular selective C-H silylation of 1,1′-biaryl-2-acetamides is described. The combination of palladium catalyst with copper oxidant enables meta- or ortho-selective C-H silylation by employing hexamethyldisilane as a trimethylsilyl source, which relies on the control of NBE derivatives as a switch, thus providing straightforward access to divergent silicon-containing 1,1′-biaryl-2-acetamides.
Li, Wenguang,Chen, Wenqi,Zhou, Bang,Xu, Yankun,Deng, Guobo,Liang, Yun,Yang, Yuan
supporting information
p. 2718 - 2722
(2019/04/16)

Metal-Free Synthesis of Pyrrolo[1,2- a ]quinoxalines Mediated by TEMPO Oxoammonium Salts
We herein describe a novel TEMPO oxoammonium salt initiated Pictet-Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2- a ]quinoxalines or 5,6-dihydroindolo[1,2- a ]quina-oxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization-dehydrogenation process using one equivalent of the oxoammonium salt.
Huo, Heng-Rui,Tang, Xiang-Ying,Gong, Yue-Fa
p. 2727 - 2740
(2018/06/20)

Synthesis and antimalarial activity of new enantiopure aminoalcoholpyrrolo[1,2-a]quinoxalines
Background: We prepared a novel series of enantiopure mefloquine analogues with pyrrolo[ 1,2-a]quinoxaline core in order to fight Plasmodium falciparum resistant strain. Objectives: To observe the influence of pyrrolo[1,2-a]quinoxaline core versus quinoline core on the antimalarial activity. Method: Four enantiopure aminoalcoholpyrrolo[1,2-a]quinoxalines 2 were synthetized via Sharpless asymmetric dihydroxylation reaction in eight steps. Their antimalarial activity was evaluated on two Plasmodium falciparum strains 3D7 and W2 with a SYBR Green I fluorescence-based method and their cytotoxicity was measured on four cell lines HepG2, THP-1, CHO and HFF. Results: IC50 values of the four compounds 2 were close to the micromolar against the two P. falciparum strains. They were more active against P. falciparum strain W2 vs. P. falciparum strain 3D7. (R)-enantiomers were always more active than their (S)-counterpart whatever the strain. Selectivity indexes of compounds 2 were lower than 100. Conclusion: A novel series of enantiopure aminoalcohols with pyrrolo[1,2-a]quinoxaline core were synthesized in eight steps. They displayed IC50 values close to the micromolar against two P. falciparum strains 3D7 and W2. Although, In this series, 2,8-bistrifluoromethylquinoline was a best core than pyrrolo[1,2-a]quinoxaline for an optimal antimalarial activity, the pyrroloquinoxaline 2b showed an interesting antimalarial activity.
Jonet, Alexia,Guillon, Jean,Mullié, Catherine,Cohen, Anita,Bentzinger, Guillaume,Schneider, Jérémy,Taudon, Nicolas,Hutter, Sebastien,Azas, Nadine,Moreau, Stephane,Savrimoutou, Solene,Agnamey, Patrice,Dassonville-Klimpt, Alexandra,Sonnet, Pascal
p. 293 - 303
(2018/05/23)

Synthesis, Characterization, and Properties of Bis-BN Ullazines
A series of bis-BN ullazine derivatives, including the parent species, were synthesized in a small number of steps from commercially available materials. X-ray crystallographic analysis revealed that bis-BN ullazines have rigid and planar frameworks. Most of the bis-BN ullazines are stable toward air and moisture. In addition, the absorption and emission bands of these ullazines are blue-shifted, compared to those of their carbonaceous ullazine analogs.
Li, Chenglong,Liu, Yuming,Sun, Zhe,Zhang, Jinyun,Liu, Meiyan,Zhang, Chen,Zhang, Qian,Wang, Hongjuan,Liu, Xuguang
supporting information
p. 2806 - 2810
(2018/05/29)

Boron nitrogen doped fused-ring aromatic hydrocarbon containing five-membered heterocyclic ring, synthesis method and application thereof
The invention relates to a boron nitrogen doped fused-ring aromatic hydrocarbon containing a five-membered heterocyclic ring, a synthesis method thereof and application thereof, the photoelectric physical properties of the boron nitrogen doped fused-ring aromatic hydrocarbon are tested, and the potential application value of the organic material in organic electrochemistry can be further studied.The improved synthesis method is used to make a reaction raw material low in price and easy to obtain, the reaction process avoids the use of toxic reagents, the synthesis method is simple and easy, and the compound is has a wide range of application in the fields of organic light emitting diodes, organic solar batteries, organic field effect transistors, organic lasers, organic sensors, molecularswitches, bio-imaging and toxin detection and the like.
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(2018/09/28)

Palladium nanoparticles stabilized by aqueous vesicles self-assembled from a PEGylated surfactant ionic liquid for the chemoselective reduction of nitroarenes
Vesicles self-assembled from an aqueous PEGylated surfactant ionic liquid solution can be applied for stabilizing palladium nanoparticles, which prove to be an efficient catalytic system for chemoselective hydrogen transfer of nitroarenes using hydrazine hydrate as a hydrogen source. The particle sizes of vesicles are decreased with the increase of ionic liquid's concentrations and relatively small particle sizes are beneficial to the reduction. Moreover, the aqueous catalytic system still stays in reactor by simple extraction, and is reused without further treatment.
Xu, Zhu-bing,Lu, Guo-ping,Cai, Chun
p. 57 - 60
(2017/06/06)

Design, synthesis and antimalarial activity of novel bis{N-[(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]-3-aminopropyl}amine derivatives
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.
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)

Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives
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.
Xie, Caixia,Zhang, Zeyuan,Li, Danyang,Gong, Jian,Han, Xushuang,Liu, Xuan,Ma, Chen
p. 3491 - 3499
(2017/04/11)

Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-: A] quinoxalines
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.
Liu, Huanhuan,Zhou, Feiyu,Luo, Wen,Chen, Yuxin,Zhang, Chenyang,Ma, Chen
p. 7157 - 7164
(2017/09/07)

Halogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol for Perfluoroalkylation Reactions
A new protocol for photochemical perfluoroalkylation reactions using perfluoroalkyl iodide, amine additive, and THF solvent is reported. This protocol does not require a photoredox catalyst and proceeds at ambient temperature with irradiation from a compact fluorescent lamp, low-intensity UV lamp, or sunlight. This protocol can be applied to the synthesis of perfluoroalkyl-substituted phenanthridines as well as effect the iodo-perfluoroalkylation of alkenes/alkynes and the C-H perfluoroalkylation of electron-rich arenes and heteroarenes. This C-H perfluoroalkylation reaction offers a unique method for site-selective labeling of oligopeptides at the tryptophan residue.
Wang, Yaxin,Wang, Junhua,Li, Guo-Xing,He, Gang,Chen, Gong
supporting information
p. 1442 - 1445
(2017/03/23)

AgI-Promoted Difluoromethylation of Isocyanides To Give Difluoromethylated Phenanthridines
An AgI-mediated ethoxycarbonyldifluoromethylation of isocyanides has been developed. This radical cascade reaction involves the addition of difluoromethylene radical to the isocyanide functionality, and subsequent homolytic aromatic substitution to give difluoromethylated phenanthridines with a good functional-group tolerance.
Wan, Wen,Xu, Xiaochen,Chen, Yunrong,Jiang, Haizhen,Wang, Yong,Deng, Hongmei,Hao, Jian
supporting information
p. 3145 - 3151
(2017/06/21)

SMALL MOLECULES INHIBITORS OF RAD51
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.
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(2017/09/15)

MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones
Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.
Wang, Sheng,Shao, Peng,Du, Gaixia,Xi, Chanjuan
p. 6672 - 6676
(2016/08/16)

Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs
Highly dispread Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes (CTH) using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with corresponding single-component catalysts, optimal composition of the Ni-Co BMNPs was screened which was proved to be crucial in both the selectivity and yields. Excellent performance of Ni-Co BMNPs can be ascribed to the improved dispersion of active sites on the BMNPs surface (compared with Ni NPs) and the electron transfer from cobalt to nickel.
Zhang, Jia-Wei,Lu, Guo-Ping,Cai, Chun
p. 25 - 29
(2016/06/13)

Harnessing the pyrroloquinoxaline scaffold for FAAH and MAGL interaction: Definition of the structural determinants for enzyme inhibition
This paper describes the development of piperazine and 4-aminopiperidine carboxamides/carbamates supported on a pharmacogenic pyrroloquinoxaline scaffold as inhibitors of the endocannabinoid catabolizing enzymes fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). Structure-activity relationships and molecular modelling studies allowed the definition of the structural requirements for dual FAAH/MAGL inhibition and led to the identification of a small set of derivatives (compounds 5e, i, k, m) displaying a balanced inhibitory profile against both enzymes, with compound 5m being the frontrunner of the subset. Favorable calculated physico-chemical properties suggest further investigation for specific analogues.
Brindisi, Margherita,Brogi, Simone,Maramai, Samuele,Grillo, Alessandro,Borrelli, Giuseppe,Butini, Stefania,Novellino, Ettore,Allarà, Marco,Ligresti, Alessia,Campiani, Giuseppe,Di Marzo, Vincenzo,Gemma, Sandra
p. 64651 - 64664
(2016/07/23)

Design, Synthesis and Antimalarial Activity of Some New minoalcoholpyrrolo[ 1,2-A]quinoxaline Derivatives
Following our search for antimalarial compounds, novel series of piperazinylalcohol pyrrolo 1,2-A]quinoxaline derivatives 1-2 were synthesized from 2-nitroaniline or 2-Amino-3 nitrophenol and tested for in vitro activity upon the intraerythrocytic stage of W2 and 3D7 Plasmodiu falciparum strains. Biological results showed good antimalarial activity with IC50 ranging fro 0.3 to 21.1 M. In attempting to investigate the large broad-spectrum antiprotozoal activities of thes pyrrolo[1,2-A]quinoxaline derivatives, their properties toward the promastigote form of Leishmani donovani were also investigated and revealed their selective antiplasmodial profile. In parallel, the i vitro cytotoxicity of these molecules was assessed on the human HepG2 cell line. Structure-Activit relationships of these new synthetic compounds are here discussed.
Guillon, Jean,Moreau, Stéphane,Ronga, Luisa,Basmacyian, Louise,Cohen, Anita,Rubio, Sandra,Bentzinger, Guillaume,Savrimoutou, Solène,Azas, Nadine,Mullié, Catherine,Sonnet, Pascal
p. 932 - 942
(2016/11/02)

Efficient synthesis of pyrrolo[1,2-: A] quinoxalines catalyzed by a Br?nsted acid through cleavage of C-C bonds
An efficient and convenient one-pot domino reaction for the direct synthesis of pyrrolo[1,2-a]quinoxalines has been developed. This approach utilizes an imine formation reaction, SEAr reaction and cleavage of C-C bonds catalyzed by a Br?nsted acid. β-Diketones and β-keto esters are both well tolerated to give the corresponding products in moderate to excellent yields.
Xie, Caixia,Feng, Lei,Li, Wanli,Ma, Xiaojun,Ma, Xinkun,Liu, Yihan,Ma, Chen
supporting information
p. 8529 - 8535
(2016/09/28)

Iridium-catalyzed transfer hydrogenation of nitroarenes to anilines
A simple and general homogeneous catalyst system composed of commercially available [Ir(cod)Cl]2 and 1,10-phenanthroline has been developed for the selective transfer hydrogenation of nitroarenes to anilines. It utilized the readily accessible 2-propanol as a hydrogen donor and had wide substrate scope. A careful mechanistic investigation through real-time detection and a series of controlled experiments with possible intermediates was also carried out, which showed that the transformation proceeds via both phenylhydroxylamine and azobenzene intermediates and the reduction of hydrazobenzene leading to aniline might be the rate-determining step.
Chen, Shujie,Lu, Guoping,Cai, Chun
p. 5360 - 5365
(2015/07/07)

A Radical-Mediated Approach to the Total Synthesis of Fluorinated Marinoquinoline A and Related Tricyclic and Tetracyclic Congeners
A radical-mediated approach to the core structure of fluorinated marinoquinoline A, N-methylated marinoquinoline A and related congeners via the use of Togni's reagent is described.
Patel, Bhaven,Hilton, Stephen T.
p. 79 - 83
(2015/02/05)

Gold(I)/chiral br??nsted acid catalyzed enantioselective hydroamination-hydroarylation of alkynes: The effect of a remote hydroxyl group on the reactivity and enantioselectivity
The catalytic enantioselective hydroamination-hydroarylation of alkynes under the catalysis of (R3P)AuMe/(S)-3,3a?2-bis(2,4,6-triisopropylphenyl)-1,1a?2-bi-naphthyl-2,2a?2-diyl hydrogenphosphate ((S)-TRIP) is reported. The alkyne was reacted with a range of pyrrole-based aromatic amines to give pyrrole-embedded aza-heterocyclic scaffolds bearing a quaternary carbon center. The presence of a hydroxyl group in the alkyne tether turned out to be very crucial for obtaining products in high yields and enantioselectivities. The mechanism of enantioinduction was established by carefully performing experimental and computational studies.
Shinde, Valmik S.,Mane, Manoj V.,Vanka, Kumar,Mallick, Arijit,Patil, Nitin T.
supporting information
p. 975 - 979
(2015/02/05)

Synthesis, antifungal activity and QSAR of some novel carboxylic acid amides
A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC50 = 16.75 μg/mL) and Rhizoctonia solani (EC50 = 19.19 μg/mL), compared to the reference compound boscalid with EC50 values of 10.68 and 14.47 μg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.
Du, Shijie,Lu, Huizhe,Yang, Dongyan,Li, Hong,Gu, Xilin,Wan, Chuan,Jia, Changqing,Wang, Mian,Li, Xiuyun,Qin, Zhaohai
p. 4071 - 4087
(2015/05/13)

Synthesis, antifungal activity and structure-activity relationships of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides
A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.
Du, Shijie,Tian, Zaimin,Yang, Dongyan,Li, Xiuyun,Li, Hong,Jia, Changqing,Che, Chuanliang,Wang, Mian,Qin, Zhaohai
p. 8395 - 8408
(2015/05/20)

Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible-light photoredox catalysis
A mild and facile method for preparing highly functionalized pyrrolo[1,2-a]quinoxalines and other nitrogenrich heterocycles, each containing a quinoxaline core or an analogue thereof, has been developed. The novel method features a visible-light-induced decarboxylative radical coupling of ortho-substituted arylisocyanides and radicals generated from phenyliodine(III) dicarboxylate reagents and exhibits excellent functional group compatibility. A wide range of quinoxaline heterocycles have been prepared. Finally, a telescoped preparation of these polycyclic compounds by integration of the in-line isocyanide formation and photochemical cyclization has been established in a three-step continuousflow system.
He, Zhi,Bae, Minwoo,Wu, Jie,Jamison, Timothy F.
supporting information
p. 14451 - 14455
(2015/02/19)

Design, synthesis and biological evaluation of novel 4- alkapolyenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents - Part III
A series of new 4-alkapolyenylpyrrolo[1,2-a]quinoxaline derivatives, original and structural analogues of alkaloid chimanine B and of previously described 4-alkenylpyrrolo[1,2-a]quinoxalines, was synthesized in good yields using efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. These new compounds were tested for in vitro antiparasitic activity upon three Leishmania spp. strains. Biological results showed activity against the promastigote forms of L. major, L. mexicana and L. donovani with IC50 ranging from 1.2 to 14.7 μM. In attempting to investigate if our pyrrolo[1,2-a]quinoxaline derivatives are broad-spectrum antiprotozoal compounds activities toward one Trypanosoma brucei brucei strain and the W2 and 3D7 Plasmodium falciparum strains were also investigated. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Structure-activity relationships of these new synthetic compounds are here discussed.
Ronga, Luisa,Del Favero, Marco,Cohen, Anita,Soum, Claire,Le Pape, Patrice,Savrimoutou, Solène,Pinaud, No?l,Mullié, Catherine,Daulouede, Sylvie,Vincendeau, Philippe,Farvacques, Natacha,Agnamey, Patrice,Pagniez, Fabrice,Hutter, Sébastien,Azas, Nadine,Sonnet, Pascal,Guillon, Jean
p. 378 - 393
(2014/06/09)

Discovery of pyrrolo-benzo-1,4-diazines as potent Nav1.7 sodium channel blockers
A series of pyrrolo-benzo-1,4-diazine analogs have been synthesized and displayed potent Nav1.7 inhibitory activity and moderate selectivity over Nav1.5. The syntheses, structure-activity relationships, and selected pharmacokinetic data of these analogs are described. Compound 41 displayed anti-nociceptive efficacy in the rat CFA pain model at 100 mpk oral dosing.
Ho, Ginny D.,Tulshian, Deen,Bercovici, Ana,Tan, Zheng,Hanisak, Jennifer,Brumfield, Stephanie,Matasi, Julius,Heap, Charles R.,Earley, William G.,Courneya, Brandy,Jason Herr,Zhou, Xiaoping,Bridal, Terry,Rindgen, Diane,Sorota, Steve,Yang, Shu-Wei
p. 4110 - 4113
(2014/11/07)

Synthesis of heteroaromatic derivatives with nitrogen atoms: Tripyrrolyl pyrimidine and tripyrrolyl[1,3,5]triazine
As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1- yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.
Lee,Lee,Jung,Hahn
p. 501 - 504
(2013/02/22)

Reactions of 2-(pyrrol-1-yl)benzyl radicals and related species under flash vacuum pyrolysis conditions
2-(Pyrrol-1-yl)phenoxyl, aminyl, thiophenoxyl and benzyl radicals 2a-2d, respectively, were generated in the gas-phase under flash vacuum pyrolysis conditions. In all cases except the phenoxyl, cyclisation took place providing acceptable synthetic routes to the fused heterocycles 11, 14 and 15, respectively. Only sigmatropic rearrangement products were isolated, in low yields, from the phenoxyl 2a. The pyrrolo[1,2-a]benzimidazole 11 adopts the 1H-tautomer exclusively in chloroform solution. Electrophilic substitution reactions of pyrrolo[2,1-b]benzothiophene 14 were studied, including protonation, deuterium exchange, Vilsmeier formylation and reaction with dimethyl acetylenedicarboxylate. 2-(2,5-Diarylpyrrol-1-yl)thiophenoxyl, phenoxyl and aminyl radicals 23a-f, were also generated in the gas-phase under similar conditions. The thiophenoxyls 23a/b gave extremely complex pyrolysate mixtures in which primary cyclisation products were formed by attack of the radical at the pyrrrole ring and attack at the ipso-, ortho- and meta- positions of the aryl ring. Secondary pyrolysis products were obtained by specific sigmatropic shifts of the N-aryl group. The 2,5-di(thien-2-yl)thiophenoxyl radical 23c gave the pyrrolobenzothiazole 31c as the only cyclisation product in low yield. FVP of the phenoxyl and aminyl radical generators 26d and 26f, respectively, gave 3-arylpyrrolo[1,2-f]phenanthridines 46d and 46f, respectively, by a hydrogen transfer-cyclisation mechanism.
Cadogan,Clark, Bernard A. J.,Ford, Daniel,MacDonald, Ranald J.,MacPherson, Andrew D.,McNab, Hamish,Nicolson, Iain S.,Reed, David,Sommerville, Craig C.
experimental part
p. 5173 - 5183
(2010/04/03)

New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: Synthesis, and in vitro antimalarial activity
Following our search for antimalarial compounds, novel series of ferrocenic pyrrolo[1,2-a]quinoxaline derivatives 1-2 were synthesized from various substituted nitroanilines and tested for in vitro activity upon the erythrocytic development of Plasmodium falciparum strains with different chloroquine-resistance status. The pyrrolo[1,2-a]quinoxalines 1 were prepared in 6-8 steps through a regioselective palladium-catalyzed monoamination by coupling 4-chloropyrrolo[1,2-a]quinoxalines with 1,3-bis(aminopropyl)piperazine or -methylamine using Xantphos as the ligand. The ferrocenic bispyrrolo[1,2-a]quinoxalines 2 were prepared by reductive amination of previously described bispyrrolo[1,2-a]quinoxalines 9 with ferrocene-carboxaldehyde, by treatment with NaHB(OAc)3. The best results were observed with ferrocenic pyrrolo[1,2-a]quinoxalines linked by a bis(3-aminopropyl)piperazine. Moreover, it was observed that a methoxy group on the pyrrolo[1,2-a]quinoxaline nucleus and no substitution on the terminal N-ferrocenylmethylamine function enhanced the pharmacological activity. Selected compounds 1b, 1f-h, 1l and 2a were tested for their ability to inhibit β-haematin formation, the synthetic equivalent of hemozoin, by using the HPIA (heme polymerization inhibitory activity) assay. Of the tested compounds, only 2a showed a β-haematin formation inhibition, but no inhibition of haem polymerization was observed with the other selected ferrocenic monopyrrolo[1,2-a]quinoxaline derivatives 1b, 1f-h and 1l, as the IC50 values were superior to 10 equivalents.
Guillon, Jean,Moreau, Stephane,Mouray, Elisabeth,Sinou, Veronique,Forfar, Isabelle,Fabre, Solene Belisle,Desplat, Vanessa,Millet, Pascal,Parzy, Daniel,Jarry, Christian,Grellier, Philippe
scheme or table
p. 9133 - 9144
(2009/04/11)

Synthesis of omeprazole analogues and evaluation of these as potential inhibitors of the multidrug efflux pump NorA of Staphylococcus aureus
A series of 11 pyrrolo[1,2-α]quinoxaline derivatives, 1a to 1k, sharing structural analogies with omeprazole, a eukaryotic efflux pump inhibitor (EPI) used as an antiulcer agent, was synthesized. Their inhibitory effect was evaluated using Staphylacoccus aureus strain SA-1199B overexpressing NorA. By determinations of the MIC of norfloxacin in the presence of these EPIs devoid of intrinsic antibacterial activity and used at 128 μg/ml, and by the checkerboard method, compound 1e (MIC decrease, 16-fold; fractional inhibitory concentration index [ΣFIC], 0.18) appeared to be more active than compounds 1b to 1d, reserpine, and omeprazole (MIC decrease, eightfold; ΣFIC, 0.31), followed by compounds 1a and 1f (MIC decrease, fourfold; ΣFIC, 0.37) and 1g to 1k (MIC decrease, twofold; ΣFIC, 0.50 to 0.56). By time-kill curves combining norfloxacin (1/4 MIC) and the most efficient EPIs (128 μg/ml), compound 1e persistently restored the bactericidal activity of norfloxacin (inoculum reduction, 3 log10 CFU/ml at 8 and 24 h), compound If led to a delayed but progressive decrease in the number of viable cells, and compounds 1b to 1d and omeprazole acted synergistically (inoculum reduction, 3 log10 CFU/ml at 8 h but further regrowth), while compound 1a and reserpine slightly enhanced norfloxacin activity. The bacterial uptake of norfloxacin monitored by high-performance liquid chromatography confirmed that compounds 1a to 1f increased antibiotic accumulation, as did reserpine and omeprazole. Since these EPIs did not disturb the Δψ and ΔpH, they might directly interact with the pump. A structure-activity relationships study identified the benzimidazole nucleus of omeprazole as the main structural element involved in efflux pump inhibition and highlighted the critical role of the chlorine substituents in the stability and efficiency of compounds 1e to 1f. However, further pharmacomodulation is required to obtain therapeutically applicable derivatives. Copyright
Vidaillac, Celine,Guillon, Jean,Arpin, Corinne,Forfar-Bares, Isabelle,Ba, Boubakar B.,Grellet, Jean,Moreau, Stephane,Caignard, Daniel-Henri,Jarry, Christian,Quentin, Claudine
p. 831 - 838
(2007/10/03)

Synthesis, analytical behaviour and biological evaluation of new 4-substituted pyrrolo[1,2-a]quinoxalines as antileishmanial agents
An original series of 4-substituted pyrrolo[1,2-a]quinoxaline derivatives, new structural analogues of Galipea species quinoline alkaloids, was synthesized from various substituted 2-nitroanilines via multistep heterocyclizations and tested for in vitro antiparasitic activity upon Leishmania amazonensis and Leishmania infantum strains. Structure-activity relationships enlighten the importance of the 4-substituted alkenyl side chain on the pyrrolo[1,2-a]quinoxaline moiety to modulate the antileishmanial activity.
Guillon, Jean,Forfar, Isabelle,Mamani-Matsuda, Maria,Desplat, Vanessa,Saliege, Marion,Thiolat, Denis,Massip, Stephane,Tabourier, Anais,Leger, Jean-Michel,Dufaure, Benoit,Haumont, Gilbert,Jarry, Christian,Mossalayi, Djavad
p. 194 - 210
(2008/02/01)

Synthesis, Antimalarial Activity, and Molecular Modeling of New Pyrrolo[1,2-a]quinoxalines, Bispyrrolo[1,2-a]quinoxalines, Bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and Bispyrrolo[1,2-a]thieno[3,2-e]pyrazines
Three pyrrolo[1,2-a]quinoxalines, 15 bispyrrolo[1,2-a]quinoxalines, bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno[3,2-e]pyrazines were synthesized from various substituted nitroanilines or nitropyridines and tested for their in vitro activity upon the erythrocytic development of Plasmodium falciparum strains with different chloroquine-resistance status. Bispyrrolo[1,2-a]quinoxalines showed superior antimalarial activity with respect to monopyrrolo[1,2-a]quinoxalines. The best activity was observed with bispyrrolo[1,2-a]quinoxalines linked by a bis(3-aminopropyl)piperazine. Moreover, it was observed that the presence of a methoxy group on the pyrrolo[1,2-a]quinoxaline nucleus increased the pharmacological activity. Drug effects upon β-hematin formation were assayed and showed similar or higher inhibitory activities than CQ. A possible mechanism of interaction implicating binding of pyrroloquinoxalines to β-hematin was supported by molecular modeling.
Guillon, Jean,Grellier, Philippe,Labaied, Mehdi,Sonnet, Pascal,Léger, Jean-Michel,Déprez-Poulain, Rébecca,Forfar-Bares, Isabelle,Dallemagne, Patrick,Lema?tre, Nicolas,Péhourcq, Fabienne,Rochette, Jacques,Sergheraert, Christian,Jarry, Christian
p. 1997 - 2009
(2007/10/03)

Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.
Antilla, Jon C.,Baskin, Jeremy M.,Barder, Timothy E.,Buchwald, Stephen L.
p. 5578 - 5587
(2007/10/03)

Pharmaceutically active pyrrolidine derivatives
The present invention is related to pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of premature labor, premature birth and dysmenorrhea. In particular, the present invention is related to pyrrolidine derivatives displaying a substantial modulatory, notably an antagonist activity of the oxytocin receptor. More preferably, said compounds are useful in the treatment and/or prevention of disease states mediated by oxytocin, including premature labor, premature birth and dysmenorrhea. The present invention is furthermore related to novel pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of CR6R7, NOR6, NNR6R7; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO22—, —SO2NH—, —CH2—,B is either a group —(C═O)—NR8R9 or represents a heterocyclic residue having the formula (a) wherein Q is NR10, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.
-
(2008/06/13)

Pharmaceutically active pyrrolidine derivatives as bax inhibitors
The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating-up to an inhibitory-activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CRR, NOR, NNRR; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO2-, —SO2NH—; —CH2-; B is either a group —(C═O)—NRR or represents a heterocyclic residue having the formula (II) wherein Q is NR, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.
-
(2008/06/13)

Benzamide derivatives having a vasopressin antagonistic activity
This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc. and represented by general formula (I): wherein R1is aryl optionally substituted with lower alkoxy, etc., R2is lower alkyl, etc., R3is hydrogen, etc., A is NH, etc., E is etc., X is —CH═CH—, —CH═N—, or S, and Y is a condensed heterocyclic group, etc., and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.
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(2008/06/13)

Synthesis of new pyrrolo[l,2-a]quinoxalines: Potential non-peptide glucagon receptor antagonists
Synthesis of new pyrrolo[1,2-a]quinoxaline derivatives was achieved starting from various nitroanilines or orthophenyle-nediamines. Their affinity towards glucagon receptors was evaluated. Elsevier, Paris.
Guillon, Jean,Dallemagne, Patrick,Pfeiffer, Bruno,Renard, Pierre,Manechez, Dominique,Kervran, Alain,Rault, Sylvain
p. 293 - 308
(2007/10/03)

Synthesis and antituberculosis activity of new phenylpyrrolo[1,2-a] quinoxalinylpyrrole carboxylic acid derivatives
During the course of our work on the synthesis and screening of new drugs for tuberculosis, we have identified three new phenylpyrrolo[1,2-a]quinoxalinylpyrrole carboxylic acid derivatives which inhibited in-vitro Mycobacterium tuberculosis H37Rv; 97-98% inhibition at 12.5 μg mL-1.
Guillon,Dumoulin,Dallemagne,Reynolds,Rault
p. 33 - 38
(2007/10/03)