- Benzimidazole scaffold based hybrid molecules for various inflammatory targets: Synthesis and evaluation
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Designing of hybrid drugs with specific multitarget profile is a promising line of attack against inflammation. In light of this, a series of benzimidazole scaffold based hybrid molecules were designed by integrating benzimidazoles (containing pharmacophoric elements for COXs and LOXs inhibitors) with phthalimide subunit of thalidomide (pharmacophore element for TNF-α inhibitor) under one construct via molecular hybridization strategy. The designed molecules were synthesized and evaluated for their inhibitory activity against COXs (COX-1, COX-2), LOXs (5-LOX, 15-LOX) enzymes as well as TNF-α inhibitory effect. The results revealed that, compounds (3a–l) obtained showed inhibition in submicromolar range against COXs and LOXs targets whereas milder inhibitory activity was obtained against lipopolysaccharides (LPS)-induced TNF-α secretion by murine macrophage-like cells (RAW264.7). Within this class of compounds, 3j emerged as having alluring multiple inhibitory effects on set of COX-1/2 and 5-/15-LOX enzymes (COX-1 IC50 = 9.85 μM; COX-2 IC50 = 1.00 μM; SI = 9.85; 5-LOX IC50 = 0.32 μM; 15-LOX IC50 = 1.02 μM) in conjunction with a good anti-inflammatory and analgesic activities. Additionally, compound 3j showed gastrointestinal safety with reduced lipid peroxidation. Docking results of compound 3j with COX-2 and 5-LOX were also consistent with the in vivo anti-inflammatory results.
- Kaur, Gaganpreet,Silakari, Om
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Read Online
- Design, synthesis and biological evaluation of 2-(2-amino-5(6)-nitro-1H-benzimidazol-1-yl)-narylacetamides as antiprotozoal agents
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Parasitic diseases are a public health problem affecting millions of people worldwide. One of the scaffolds used in several drugs for the treatment of parasitic diseases is the benzimidazole moiety, a heterocyclic aromatic compound. This compound is a crucial pharmacophore group and is considered a privileged structure in medicinal chemistry. In this study, the benzimidazole core served as a model for the synthesis of a series of 2-(2-amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides 1-8 as benznidazole analogues. The in silico pharmacological results calculated with PASS platform exhibited chemical structures highly similar to known antiprotozoal drugs. Compounds 1-8 when evaluated in silico for acute toxicity by oral dosing, were less toxic than benznidazole. The synthesis of compounds 1-8 were carried out through reaction of 5(6)-nitro- 1H-benzimidazol-2-amine (12) with 2-chlroactemides 10a-h, in the presence of K2CO3 and acetonitrile as solvent, showing an inseparable mixture of two regioisomers with the -NO2 group in position 5 or 6 with chemical yields of 60 to 94%. The prediction of the NMR spectra of molecule 1 coincided with the experimental chemical displacements of the regioisomers. Comparisons between the NMR prediction and the experimental data revealed that the regioisomer endo-1,6-NO2 predominated in the reaction. The in vitro antiparasitic activity of these compounds on intestinal unicellular parasites (Giardia intestinalis and Entamoeba histolytica) and a urogenital tract parasite (Trichomonas vaginalis) were tested. Compound 7 showed an IC50 of 3.95 μM and was 7 time more active against G. intestinalis than benznidazole. Compounds 7 and 8 showed 4 times more activity against T. vaginalis compared with benznidazole.
- Hernández-Nú?ez, Emanuel,Tlahuext, Hugo,Moo-Puc, Rosa,Moreno, Diego,González-Díaz, María Ortencia,Vázquez, Gabriel Navarrete
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Read Online
- 1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation
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Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.
- Venter, Jana,Perez, Concepción,van Otterlo, Willem A.L.,Martínez, Ana,Blackie, Margaret A.L.
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p. 1597 - 1600
(2019/05/02)
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- Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines
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An operationally simple oxidation-cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.
- Kuhl, Nadine,Raval, Saurin,Cohen, Ryan D.
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supporting information
p. 1268 - 1272
(2019/03/07)
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- INDOLE DERIVATIVE, PREPARATION METHOD THEREOF, AND USE THEREOF IN PHARMACEUTICAL DRUG
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An indole derivative as expressed by Formula (I), a preparation method thereof, a pharmaceutical salt, and use thereof as a therapeutic agent, especially as a FGFR inhibitor. Each substituent in Formula (I) has identical definition as specified in the specification.
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Paragraph 0085; 0086
(2018/07/06)
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- COMPOUNDS AND METHODS FOR TREATMENT OF CANCER BY INHIBITING ATG4B AND BLOCKING AUTOPHAGY
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ATG4B inhibitor compounds, compositions that include the compounds, and methods for using the compounds and compositions in the treatment of cancer by inhibiting ATG4B and/or blocking autophagy.
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Page/Page column 56; 57
(2017/03/14)
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- 5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES
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The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
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Page/Page column 240
(2017/09/27)
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- Copper-Catalyzed C NH2Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles
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A copper(II)-catalyzed selective C NH2arylation of 2-aminobenzimidazoles and related C-amino-NH-azoles was achieved in presence of 2,2′-bipyridine and cesium carbonate at 60 °C under open air conditions and this is first method for the copper-catalyzed selective C NH2arylation in the presence of other reactive nucleophilic sites. Previously unexplored heteroaromatics possessing multiple nucleophilic sites that are selectively arylated at the C NH2position are obtained, providing an exceptional tool for rapid delivery of a diverse array of medicinally important C NH(aryl) derivatives of aminoazoles without any protection/deprotection of ring N H bonds. It is first example for the selective C NH2arylation of 5-aminoindazole, 4-aminopyrazole, 5-aminopyrazole, 9H-purine-6-amine, and 1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives. (Figure presented.) .
- Rao, Desaboini Nageswar,Rasheed, Sk.,Kumar, Karampoori Anil,Reddy, Annem Siva,Das, Parthasarathi
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supporting information
p. 2126 - 2133
(2016/07/16)
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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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- 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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- Copper-catalyzed sequential N-arylation of C-amino-NH-azoles
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Copper(ii)-catalyzed boronic acid promoted C-N bond cross-coupling reactions have been successfully developed for sequential N-arylation of C-amino-NH-azoles. These general protocols are compatible with a variety of aryl/hetero-aryl boronic acids and provided rapid access to a diverse array of diarylaminoazole derivatives in a two-step sequence or in one-pot. This journal is
- Nageswar Rao,Rasheed, Sk.,Vishwakarma, Ram A.,Das, Parthasarathi
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supporting information
p. 12911 - 12914
(2014/12/11)
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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; 0230; 0231
(2013/06/05)
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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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- Design, synthesis and antiproliferative properties of some new 5-substituted-2-iminobenzimidazole derivatives
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Some new 1,3,5-substituted-2,3-dihydro-2-imino-benzimidazoles were synthesized under solid-liquid phase transfer catalysis conditions using 5-substituted-2-aminobenzimidazoles as precursors in order to assess their cytotoxicity respectively proliferative activity. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. Compounds 9-10, 12 and 16-17 were evaluated for their cytotoxical effect on four cancer cell lines: HT-29, breast cancer cells MDA-MB-231, HeLa, HepG2 and as well as human diploid cell line Lep-3. Significant cytotoxicity of hydrazone 16 against MDA-MB-231 was established by biologically study, the IC50 was 6.2 nM while the EC50 value to Lep 3 is 0.21 nM. Relative high antiproliferative effects of the acetate 12 and compound 16 against HT-29 were ascertained and the calculated IC50 values were IC50 - 0.85 nM and IC50 - 2.83 nM respectively. Cytotoxic activity against HeLa and HepG2 cells was demonstrated by hydrazone 17, IC50 was 7.2 nM and 117 nM respectively. All tested compounds revealed proliferative activities to human diploid cell line Lep-3. The EC50 values were in the range from 0.05 to 16.91 nM. The obtained results prove the selective cytotoxicity of the tested compounds and are promising for further evaluation of the investigated compounds in vivo experiments using experimentally induced tumors in laboratory animals.
- Mavrova, Anelia Ts.,Wesselinova, Diana,Vassilev, Nikolay,Tsenov, Jordan A.
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p. 696 - 701
(2013/07/27)
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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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- 2-amino-X-nitrobenzimidazoles as precursors of food-borne carcinogens: A new approach to IQ synthesis
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Cyclization of (non)-methylated nitro-o-phenylenediamines with cyanogen bromide provided nitro-substituted 2-aminobenzimidazoles in good up to excellent yields. Catalytic hydrogenation of 2-amino-1-methyl-5-nitrobenzimidazole yielded 2,5-diamino-1-methylbenzimidazole, which on treatment with 1,1,3,3-tetramethoxypropane in methanol and subsequently after removal of methanol in polyphosphoric acid afforded food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in 20% yield. Copyright
- Bella, Maros,Milata, Viktor,Larina, Lyudmila I.
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experimental part
p. 293 - 296
(2012/06/04)
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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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- The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii
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Multidrug-resistant bacterial infections continue to be a rising global health concern. Herein is described the development of a class of novel 2-aminobenzimidazoles with antibiotic activity. These active 2-aminobenzimidazoles retain their antibiotic activity against several strains of multidrug-resistant Staphylococcus aureus and Acinetobacter baumannii when compared to susceptible strains.
- Huigens III, Robert W.,Reyes, Samuel,Reed, Catherine S.,Bunders, Cynthia,Rogers, Steven A.,Steinhauer, Andrew T.,Melander, Christian
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supporting information; experimental part
p. 663 - 674
(2010/05/02)
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- The design, synthesis and biological evaluation of 7-alkoxy-4-heteroarylamino-3-cyanoquinolines as dual inhibitors of c-Src and iNOS
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Because both c-Src and iNOS are key regulatory enzymes in tumorigenesis, a new series of 4-heterocycle amine-3-quinolinecarbonitriles as potent dual inhibitors of both enzymes were designed, synthesized and evaluated as multiple targets agents in cancer therapy. All compounds were evaluated by two related enzyme inhibition assays and an anti-proliferation assay in vitro. The results showed that most compounds inhibited c-Src and iNOS well. The best compound 8 inhibited both enzymes with the IC50 values of 34.8 nM and 26.7 μM. Several compounds also showed moderate anti-proliferation at 10 μM against colon and liver cancer cell lines.
- Cao, Xin,You, Qi-Dong,Li, Zhi-Yu,Liu, Xiao-Rong,Xu, Dan,Guo, Qing-Long,Shang, Jing,Chern, Ji-Wang,Chen, Meng-Ling
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scheme or table
p. 6206 - 6209
(2009/07/18)
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- Synthesis and cytostatic evaluation of pyridopyrimidobenzimidazole derivatives
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A set of novel 2,5-substituted benzimidazoles (1-7) and their cyclic derivatives (8-11) were synthesized and evaluated for their potential cytostatic effect on various tumor cell lines. The structures of the synthesized compounds were proved by means of IR, 1H NMR and MS spectral data. Based on presented in vitro screening results we may conclude that cyclic compounds bearing nitro and amino substituents (10 and 11) showed the most pronounced growth inhibitory.
- Starcevic, Kristina,Kralj, Marijeta,Ester, Katja,Karminski-Zamola, Grace
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p. 647 - 656
(2008/03/13)
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- Identification of 1-isopropylsulfonyl-2-amine benzimidazoles as a new class of inhibitors of hepatitis B virus
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A series of 1-isopropylsulfonyl-2-amine benzimidazole derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. In general, these derivatives are potent HBV inhibitors (IC
- Li, Yun-Fei,Wang, Gui-Feng,Luo, Yu,Huang, Wei-Gang,Tang, Wei,Feng, Chun-Lan,Shi, Li-Ping,Ren, Yu-Dan,Zuo, Jian-Ping,Lu, Wei
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p. 1358 - 1364
(2008/09/17)
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- 2,5- and 2,6-disubstituted benzazole analogues useful as protein kinase inhibitors
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The present invention relates to compounds of the general formulas (I), (Ia) and (II) and salts and physiologically functional derivatives thereof, wherein the substituents -Y are attached to the 5- or 6- position of the benzazole. These compounds are useful as protein kinase inhibitors in the treatment of i.a. cancer.
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Page/Page column 25
(2008/06/13)
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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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- Synthesis, crystal structure determination and antiproliferative evaluation of novel benzazoyl benzamides
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A series of benzazoyl-benzamides containing different substituents (7-17) were synthesized by condensation of 2-aminobenzazole derivatives (3a-6) with p-substituted benzoyl chlorides. All compounds were characterized by IR, 1H and 13C NMR, MS and elemental analysis. Crystal structure was determined for the compound (9). Some of the new synthesized compounds (7-17) were screened for antitumor activities. Based on presented in vitro screening results we may conclude that compounds (10, 15a, 15b and 16) showed accentuated cell growth inhibitory activity.
- Starcevic, Kristina,Caleta, Irena,Cincic, Dominik,Kaitner, Branko,Kralj, Marijeta,Ester, Katja,Karminski-Zamola, Grace
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p. 2285 - 2299
(2007/10/03)
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- Toward bifunctional antibody catalysis
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Antibodies that catalyze the deprotonation of unactivated benzisoxazoles to give the corresponding salicylonitriles were prepared using as antigen a 2-aminobenzimidazolium derivative coupled to a carrier protein via its benzene ring. The hapten was designed to induce an antibody binding site with both a base and an acid, in position to initiate proton transfer and stabilize developing negative charge at the phenoxide leaving group, respectively. Consistent with this design, the catalysts exhibit bell-shaped pH-rate profiles, while chemical modification identified several functional groups that could participate in bifunctional catalysis. One of the antibodies, 13G5, is particularly notable in catalyzing the elimination of 6-glutaramidebenzisoxazole with a >105-fold rate acceleration over background and an effective molarity of >104 M for its catalytic base. These properties compare favorably to the efficiencies achieved by the best previously characterized antibodies with substantially more reactive substrates.
- Kikuchi, Kazuya,Hannak, Renate B.,Guo, Mao-Jun,Kirby, Anthony J.,Hilvert, Donald
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p. 6189 - 6196
(2007/10/03)
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- Pyridinium azolate betaines and their derivatives: A new class of antiprotozoal agents
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N-azolylpyridinium salts 1 and several betaines of pyridinium azolate 2 have been synthesized in order to study their in vitro antiprotozoal activity. A careful 1H and 13C-NMR study has been carried out in order to characterize the different compounds. A significant growth inhibition of Trypanosoma cruzi and especially Leishmania donovani was observed with the N-benzimidazolylpyridinium derivatives. When tested in vivo against Leishmania donovani, compounds 9 and 40 have had a much greater reducing effect in the parasite than that of the reference drug (glucantime).
- Alcalde,Dinares,Elguero,Frigola,Osuna,Castanys
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p. 309 - 319
(2007/10/02)
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- Iminoisoindolinone metal complex
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Iminoisoindolinone metal complexes of formula STR1 wherein A represents a 5- or 6-membered heterocyclic radical which contains at least one further heteroatom and can be fused or doubled with benzene nuclei, M represents a divalent metal atom excluding the alkaline earth metals, X represents a hydrogen atom, Y represents a halogen atom, Z represents a nitro group, an alkoxycarbonyl group of 2 to 6 carbon atoms or a group of formula RY2 --, wherein R represents a hydrogen atom, an alkyl group of 1 to 6 carbon atoms which is substituted by an aryl radical or is unsubstituted, a cycloalkyl group of 5 to 6 carbon atoms, or represents an aryl group, and Y2 represents an oxygen or a sulphur atom, m and n are 0 to 4, p is 0 to 2, and the sum of m+n+p must be 4, which are useful for pigmenting high molecular organic material.
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