- MRGX Receptor Antagonists
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The invention relates to a method for preventing or treating a disease or disorder that is associated with the MrgX2 receptor. The invention also relates to MrgX2 antagonists and physiologically acceptable salts thereof. The invention also relates to pharmaceutical compositions and dosage forms comprising an MrgX2 antagonist.
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Paragraph 0277; 0289; 0288
(2021/05/07)
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- Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
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Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.
- Giancotti, Gilda,Cancellieri, Michela,Balboni, Andrea,Giustiniano, Mariateresa,Novellino, Ettore,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella
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supporting information
p. 56 - 68
(2018/03/06)
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- Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles
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A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones. (Figure presented.).
- Kong, Weiguang,Zhou, Yao,Song, Qiuling
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supporting information
p. 1943 - 1948
(2018/04/02)
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- Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources
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A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C-C bond and C-N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot protocol is reported for the first time. This reaction features broad substrate scope, good functional group tolerance, as well as diversified and valuable products.
- Rao, Changqing,Mai, Shaoyu,Song, Qiuling
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supporting information
p. 4726 - 4729
(2017/09/22)
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- Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles
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Two groups of benzimidazole derivatives were synthesized using as precursors 5(6)-substituted 2-mercapto-benzimidazol-thiols and their antioxidant activity was investigated using TBA-MDA test. In the group of 1,3-disubstituted-benzimidazol-2-imines the highest lipid peroxidation inhibition effect 74.04% (IC50 = 141.89 μg/mL) revealed ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimdazol-1-yl]acetate 12 while in the group of 2-substituted-1,3-thiazolo[3,2-a]benzimidazolones the highest inhibition effect showed 2-(4-fluorobenzylidene)-7-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 17 90.76% (IC50 = 53.70 μg/mL). In order to estimate the capability of the studied benzimidazoles to act as radical scavengers the structure of the most active derivative within the both subseries was optimized at B3LYP/6-311++G?? level and the respective bond dissociation enthalpies were calculated. The appropriate models for the HAT and SET-mechanism of the antioxidant activity were proposed. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and three Gram-negative bacteria (Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027 and Salmonella abony NCTC 6017). 1,3-Diphenylpropyl-5-methyl-1,3-dihydro-2H-benzimidazol-2-imine 14 exhibited significant activity against B. subtilis, S. aureus, S. abony and E. coli (with MIC values of 0.125, 0.016, 0.50 and 0.50 mg/mL, respectively). The group of thiazolobenzimidazolones did not reveal antibacterial activity against the tested strains.
- Mavrova, Anelia Ts.,Yancheva, Denitsa,Anastassova, Neda,Anichina, Kamelya,Zvezdanovic, Jelena,Djordjevic, Aleksandra,Markovic, Dejan,Smelcerovic, Andrija
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p. 6317 - 6326
(2015/10/05)
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- A facile synthesis of 2-aminobenzoxazoles and 2-aminobenzimidazoles using N -cyano- N -phenyl- P -toluenesulfonamide (NCTS) as an efficient electrophilic cyanating agent
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A facile synthesis of 2-aminobenzoxazole and 2-aminobenzimidazole derivatives employing a nonhazardous electrophilic cyanating agent: N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) with various substituted 2-aminophenols and benzene-1,2-diamine derivatives in the presence of lithium hexamethyldisilazide (LiHMDS) is described. This novel protocol boasts operational simplicity, shorter reaction time, and simple workup.
- Kasthuri, Mahesh,Babu, H. Sharath,Kumar, K. Shiva,Sudhakar, Ch.,Kumar, P. V. Nagendra
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p. 897 - 900
(2015/04/27)
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- Inhibition and Dispersion of Bacterial Biofilms with 2-Aminobenzimidazole Derivatives
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Compounds described herein inhibit biofilm formation or disperse pre-formed biofilms of Gram-negative bacteria. Biofilm-inhibitory compounds can be encapsulated or contained in a polymer matrix for controlled release. Coatings, films, multilayer films, hydrogels, microspheres and nanospheres as well as pharmaceutical compositions and disinfecting compositions containing biofilm-inhibitory compounds are also provided. Methods for inhibiting formation of biofilms or dispersing already formed biofilms are provided. Methods for treating infections of gram-negative bacteria which form biofilms, particularly those of Pseudomonas and more particularly P. aeruginosa.
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Paragraph 0216; 0217; 0234; 0235
(2013/06/05)
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- A novel route to one-pot three-component synthesis of benzimidazo [2,1-b]-quinazolin-1-one derivatives
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One-pot three-component synthesis of benzimidazo[2,1-b]-quinazolin-1-ones was efficiently performed under microwave irradiation and solvent-free condition. The method provides some advantages such as low cost, experimental simplicity, high yields, and short reaction times. The structure of newly synthesized compounds is characterized by IR, 1H-NMR, MS and elemental analysis.
- Kahveci, Bahittin,Yilmaz, Fatih,Mentese, Emre,Karaali, Nesrin
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p. 490 - 495
(2013/08/23)
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- Synthesis and QSAR modeling of novel benzimidazolo thiazolidinones, thiazinones and 5-arylidene-2-imino thiazolidinones as antibacterial agents
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A novel series of benzimidazolo thiazolidinones, thiazinones and 5-arylidene-2-imino thiazolidinones were synthesized and evaluated for antibacterial activity. The compounds were synthesized in excellent yield and the structures were characterized on the basis of IR, 1H-NMR and MASS spectral data. Most of the synthesized compounds showed good antibacterial activity against Gram-positive and Gram-negative bacteria. QSAR study was carried out with synthesized compounds using molecular descriptors such as electronic, thermodynamic and steric. Molecular descriptors were used to derive QSAR models between antibacterial activity and structural properties. QSAR study suggested the need of a bulky group to enhance the antibacterial activity in these series of compounds.
- Ghate, Manjunath,Devi, Praveena,Parikh, Jignesh,Vyas, Vivek K.
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p. 474 - 485
(2013/07/28)
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- 2-aminobenzimidazole derivatives strongly inhibit and disperse Pseudomonas aeruginosa biofilms
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Bacterial biofilms are exceptionally difficult to clear using traditional antibiotics and constitute a significant health threat. 2-Aminobenzimidazole derivatives (see scheme) are capable of strongly inhibiting the growth of and dispersing Pseudomonas aeruginosa biofilms. These molecules were found to modulate quorum sensing in reporter strains, and represent some of strongest P. aeruginosa biofilm inhibitors known. Copyright
- Frei, Reto,Breitbach, Anthony S.,Blackwell, Helen E.
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supporting information; experimental part
p. 5226 - 5229
(2012/07/03)
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- Synthesis, spectroscopic characterization and antiproliferative evaluation in vitro of novel Schiff bases related to benzimidazoles
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A series of novel benzimidazole substituted Schiff bases were synthesized by reaction of aromatic aldehydes with corresponding 2-aminobenzimidazoles. Their structure has been studied by 1H and 13C NMR, IR and UV/Vis spectroscopy. Maj
- Hranjec, Marijana,Star?evi?, Kristina,Paveli?, Sandra Kraljevi?,Lu?in, Pero,Paveli?, Kre?imir,Karminski Zamola, Grace
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scheme or table
p. 2274 - 2279
(2011/06/23)
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- Efficient synthesis of 2-arylamino-2-imidazolines and 2-aminobenzimidazoles with aminoiminomethanesulfonic acid derivatives
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A highly efficient synthesis of 2-arylamino-2-imidazolines and 2-aminobenzimidazoles from aminoiminomethanesulfonic acid derivatives is described. The method is simple and practical, generating imidazoline and benzimidazoline derivatives in excellent isolated yields.
- Mohanazadeh, Farajollah,Nami, Navabe,Hosseini, Samine Sadat
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experimental part
p. 1055 - 1058
(2012/01/04)
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- Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4
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High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.
- Powers, Jay P.,Li, Shyun,Jaen, Juan C.,Liu, Jinqian,Walker, Nigel P.C.,Wang, Zhulun,Wesche, Holger
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p. 2842 - 2845
(2007/10/03)
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- Ozonation of thioamide containing heterocycles. A new general and selective procedure for the synthesis of C-2 substituted heteroazole derivatives
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2-Mercaptoheteroazoles readily react with ozone in the presence of nucleophiles and under mild experimental conditions to form several C-2 substituted heterazoles.
- Saladino, Raffaele,Crestini, Claudia,Occhionero, Francesca,Nicoletti, Rosario
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p. 3241 - 3251
(2007/10/03)
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- Method of inhibiting the advanced glycosylation of proteins using 1,2-disubstituted-benzimidazoles
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The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, composition is disclosed which comprises 1,2-disubstituted benzimidazoles capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
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- OXIDATION OF 2-MERCAPTOBENZOHETERAZOLES BY DIMETHYLDIOXIRANE. A NEW METHOD FOR A SYNTHESIS OF C-2 SUBSTITUTED BENZIMIDAZOLE, BENZOXAZOLE, AND BENZOTHIAZOLE DERIVATIVES
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New and efficient reactions in which 2-mercaptobenzoheterazoles are selectively converted by dimethyldioxirane, under mild experimental conditions, to several C-2 substituted benzoimidazole, benzoxazole, and benzothiazole derivatives are reported.
- Frachey, Giuseppe,Crestini, Claudia,Bernini, Roberta,Saladino, Raffaele,Mincione, Enrico
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p. 2621 - 2630
(2007/10/02)
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