- Preparation of N-methoxycarbonyl-N'-[2-nitro-4(5)-propyl-thiophenyl]thiourea as prodrugs of albendazole
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N-methoxycarbonyl-N'-(2-nitro-4-propylthiophenyl)thiourea and N-methoxycarbonyl-N'-(2-nitro-5-propylthiophenyl)thiourea, prodrugs of albendazole, have been synthesized. The biotransformation in rats, after oral administration of these prodrugs to albendazole and albendazole sulphoxide, is described.
- Hernandez-Luis, Francisco,Castillo, Rafael,Yepez-Mulia, Lilian,Cedillo-Rivera, Roberto,Martinez-Vazquez, Gabriel,Morales-Hurtado, Raul,Jung, Helgi,Sanchez, Monica,Hernandez-Campos, Alicia,Viveros, Noemi,Munoz, Onofre
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Read Online
- Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
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A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
- Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
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supporting information
(2019/09/07)
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- Preparation method for 5-chloro-2-nitroaniline
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The invention discloses a preparation method for 5-chloro-2-nitroaniline. The preparation method comprises the following steps: performing nitration by using m-dichlorobenzene as a starting material to prepare 2,4-dichloronitrobenzene, adding the 2,4-dichlorobenzene and a solvent into an autoclave, adding ammonia, performing high-pressure amination, after the amination is completed, performing cooling, performing pressure filtration, removing the solvent from a filtrate, and performing refining to obtain the target product 5-chloro-2-nitroaniline. The method provided by the invention has the following advantages: (1) nitrogen dioxide is used as a nitrating reagent to replace a traditional nitric acid-sulfuric acid mixed acid nitrating agent, so that no waste acid is produced, cleanliness of an industrial synthesis reaction is improved, and environmental pollution is reduced; and (2) after the amination is completed, by-product ammonium chloride is directly removed by pressure filtration, so that an amount of waste water is small, and an amination yield is high.
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Paragraph 0017; 0019
(2018/08/28)
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- Molybdenum-Catalyzed Deoxygenation of Heteroaromatic N-Oxides and Hydroxides using Pinacol as Reducing Agent
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A molybdenum-catalyzed deoxygenation of pyridine N-oxides and N-hydroxybenzotriazoles, as well as other azole N-oxides, has been developed using pinacol as an environmentally friendly oxo-acceptor. The only by-products are acetone and water making the process a convenient alternative to established protocols in terms of waste generation. The reaction is highly chemoselective and a variety of functional groups are tolerated. The processes are usually very clean allowing the isolation of the pure deoxygenated products after a simple extraction in most cases. (Figure presented.).
- Rubio-Presa, Rubén,Fernández-Rodríguez, Manuel A.,Pedrosa, María R.,Arnáiz, Francisco J.,Sanz, Roberto
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supporting information
p. 1752 - 1757
(2017/05/22)
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- Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines
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Unusual regio- and chemoselective oxidation of aromatic amines hindered with ortho substituents (except -NH2, -NHCH3, and -OH) to the corresponding nitro compounds is described by use of nonanebis(peroxoic acid). The mechanistic investigation for selective oxidation of amines ortho-substituted with -NH2 or -OH showed the involvement of H-bonding between the ortho hydrogen of the adjacent -XH group (where X = NH, NR, or O) and an oxygen atom from the diperoxy acid. Various mono- and diamines are oxidized into corresponding mononitro derivatives in high yield and purity without employing any protection strategies. The protocol was also found to successful on the gram scale.
- Patil, Vilas Venunath,Shankarling, Ganapati Subray
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p. 7876 - 7883
(2015/09/01)
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- Identification of novel HDAC inhibitors through cell based screening and their evaluation as potential anticancer agents
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A series of benzimidazole based HDAC inhibitors have been rationally designed, synthesized and screened. The SAR of this new chemotype is described. The lead compound, 11e, showed strong activity in several cellular assays and demonstrated in vivo efficacy in mouse xenograft pancreatic cancer models.
- Wang, Tong,Sepulveda, Mario,Gonzales, Paul,Gately, Stephen
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p. 4790 - 4793
(2013/09/02)
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- Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups
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Theoretical and experimental regularities of the regioselectivity of the reduction of one of the two nitro groups in unsymmetrical dinitrobenzenes were studied. It was found that the regioselectivity of the formation of isomeric nitroanilines depends on the structure of the substrate and the nature of the reducing agent. The reduction regioselectivity model was verified, according to which radical anion protonation is the major reaction direction. Pleiades Publishing, Inc. 2006.
- Orlov,Begunov,Demidova,Rusakov
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- Chemical compounds
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Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.
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- A PROCESS FOR THE SYNTHESIS OF BISBENZIMIDAZOLES AND ITS DERIVATIONS
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A process for the synthesis of bisbenzimidazoles and its derivations comprising; (i) reacting 5 chloroaniline with zinc dust and acetic anhydride to produce 5 chloroacetanilide; (ii) reacting 5 chloroacetanilide with HN03 to produce 2-nitro-5-chloroacetanilide; (ix) adding sodium methoxide to 2-nitro-5-ch1oroaniline; (x) heating 2-nitro-5-chloroaniline, methyl piperazine, anhydrous K2CO3 and Dimethyl formamide at 100-120°C produce a mixture which is cooled by pouring ice and is filtered to obtain 5-(4'-methylpiperazin-1'-yl)-2-nitroaniline; (xi) treating 5-(4'-methylpiperazin-l'yl)-2-nitroaniline with Pd/C to produce 2-amino-4-(4'-methylpiperazin-1'-yl) aniline; (xii) refluxing a mixture of 2-amino-4-(4'-methylpiperazin-1'yl) aniline and ethyl-4-amino-3-nitrobenzenecarboximidate hydrochloride in presence of ethanol/glacial acetic acid to produce 4-[5'-(4"-methylpiperazin-1"-yl) 15 benzimidazol-2'-yl)-2-nitroaniline; (xiii) treating a solution of 4-[5'-(4"-methylpiperazin-1"-yi) benzimidazol-2'-yl)-2-nitroaniline with palladium on carbon to yield 2-amino-4-[5'-(4"-Methylpiperazin-1"-yl)benzimidazol-2'-yl]aniline; (xiv) heating 2-amino-4-[5'-(4"-Methylpiperazin-1"-yl)benzimidazol-2'-yl]aniline and 3-4-dimethoxy benzaldehyde using nitrobenzene as a solvent at 110-150°C to produce (DMA) i.e 5-(4-methylpiperazin-1-yl)-2-[2'-(3,4-dimethoxyphenyl)-5'-benzimidazolyl] benzimidazole; (ix) heating 2-amino-4-[5'-(4"-Methylpiperazin-1"-yl) benzimidazol-2'-YI] aniline and 5-Formyl-[3-methoxy-4-hydroxy benzimidazole] using nitrobenzene at 110°C to 150°C in presence of argon to produce (TBZ) i.e 5-(4-methylpiperazine-1-yl)-2-[2' (2"-(4-hydroxy-3methoxyphenyl)5"benzimidazolyl) -5'- benzimidazolyl] benzimidazole.
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- A convenient copper-catalyzed direct animation of nitroarenes with 9-alkylhydroxylamines
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O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields, ortho- or para-Animation with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c-f, 14 and 22g.
- Seko, Shinzo,Miyake, Kunihito,Kavvamura, Norio
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p. 1437 - 1444
(2007/10/03)
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- Preparation of N-aryl-S,S-diphenylsulfilimines by nucleophilic attack of N-lithio-S,S-diphenylsulfilimine on aromatic compounds
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N-Aryl-S,S-diphenylsulfilimines with unusual substitution patterns have been prepared by reacting the novel nitrogen nucleophile N-lithio-S,S- diphenylsulfilimine with a range of activated aromatic substrates. N-lithio- S,S-diphenylsulfilimine is not only able to displace chloro groups in conventional aromatic nucleophilic substitution reactions, but also, unlike S,S-diphenylsulfilimine itself, can attack at hydrogen-bearing positions in 'vicarious' aromatic nucleophilic substitutions of hydrogen.
- Claridge, Robert P.,Millar, Ross W.,Sandall, John P. B.,Thompson, Claire
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p. 10243 - 10252
(2007/10/03)
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- Benzimidazole, benzoxazole and benzothiazole compounds
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A compound of formula (I): STR1 in which: R1 represents halogen or hydroxyl, alkoxy, trihalomethyl, amino, mercapto, alkylthio, trialkylammonium, aryloxy, arylthio, arylsulfonyl, arylsulfonyloxy, cycloalkyloxy, cycloalkylthio, bicycloalkyloxy or bicycloalkylthio, Ra and Rb, which may be identical or different, represent hydrogen or alkyl, X represents oxygen or sulfur or NR, Y represents the group as defined in the description, R2 represents an optionallly substituted aryl, its optical isomers as well as its addition salts with a pharmaceutically acceptable acid or base and medicinal products containing the same are useful as interleukin-1β inhibitor.
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- Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides
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A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.
- Makosza, Mieczyslaw,Bialecki, Maciej
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p. 4878 - 4888
(2007/10/03)
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- Non-reductive conversion of 1-nitro-9,10-anthraquinone to 1-amino-9,10-anthraquinones
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Heating 1-nitro-9,10-anthraquinone 2 with ureas 4 in N,N,N',N'-tetramethylurea (TMU) at around 130 °C resulted in the displacement of the nitro group by the amino groups, leading to the corresponding aminoanthraquinones 5 in good yields.
- Suzuki,Kawakami,Maeda
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p. 9217 - 9220
(2007/10/02)
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- Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen
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Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitroanilines.
- Makosza, Mieczyslaw,Bialecki, Maciej
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p. 4784 - 4785
(2007/10/02)
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- Cardiotonic Agents. Synthesis and Cardiovascular Properties of Novel 2-Arylbenzimidazoles and Azabenzimidazoles
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Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated.Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility.The structural features that impart optimal inotropic activity are presented.The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers.To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase.Two compounds, 1 and 41, showed interesting in vitro and oral activity without side effects.They have a more potent calcium-sensitizing effect than MCI-154 and are under further investigation.
- Guengoer, Timur,Fouquet, Andre,Teulon, Jean-Marie,Provost, Daniel,Cazes, Michele,et al.
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p. 4455 - 4463
(2007/10/02)
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- Diuretic and antihypertensive benzimidazoles
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The invention relates to compounds which exhibit diuretic and antihypertensive properties and have the following structures: STR1 or pharmaceutically acceptable salts thereof, wherein: X=halogen or trifluoromethyl Y1 and Y2 =independently hydrogen, alkyl, acyl, aryl, substituted aryl or heterocycle, R1 =hydrogen, lower alkyl, aryl, substituted aryl, benzyl, substituted benzyl, aralkyl, heterocycle or substituted heterocycle, n=O or an integer from 1-4 R2 =amino, substituted amino, guanidino, substituted guanidino, halogen, alkyl, substituted alkyl, aryl, substituted aryl or heterocycle, and R3 =hydrogen, lower alkyl, aryl, substituted aryl, benzyl, substituted benzyl, aralkyl, heterocycle, substituted heterocycle or acyl.
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