- HETEROCYCLIC COMPOUND
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Provided is a compound that can have an effect of inhibiting MALT1 and is expected as useful as a prophylactic or therapeutic drug for cancer, etc. A compound represented by formula (I) [wherein each symbol is as defined in the description], a salt thereo
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Paragraph 0480-0481
(2021/10/30)
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- Molecular tunability of surface-functionalized metal nanocrystals for selective electrochemical CO2 reduction
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Organic ligands are used in homogeneous catalysis to tune the metal center reactivity; in contrast, clean surfaces are usually preferred in heterogeneous catalysis. Herein, we demonstrate the potential of a molecular chemistry approach to develop efficient and selective heterogeneous catalysts in the electrochemical CO2 reduction reaction (CO2RR). We have tailor-made imidazolium ligands to promote the CO2RR at the surface of hybrid organic/inorganic electrode materials. We used silver nanocrystals for the inorganic component to obtain fundamental insights into the delicate tuning of the surface chemistry offered by these ligands. We reveal that modifying the electronic properties of the metal surface with anchor groups along with the solid/liquid interface with tail groups is crucial in obtaining selectivities (above 90% FE for CO), which are higher than the non-functionalized Ag nanocrystals. We also show that there is a unique dependency of the CO2RR selectivity on the length of the hydrocarbon tail of these ligands, offering a new way to tune the interactions between the metal surface with the electrolyte and reactants.
- Pankhurst, James R.,Guntern, Yannick T.,Mensi, Mounir,Buonsanti, Raffaella
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p. 10356 - 10365
(2019/11/20)
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- A process for preparing 7-bromo imidazo [2,1-f] [1, 2, 4] triazin-4-amine method
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The invention discloses a method for preparing 7-bromoimidazo[2,1-f][1,2,4]triazin-4-amine. According to the invention, a compound IX is adopted as a a raw material, and is subjected to a reaction with a compound X under the effect of alkali, such that a
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Paragraph 0065-0068
(2016/11/24)
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- Synthesis and significant cytostatic activity of 7-hetaryl-7- deazaadenosines
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A series of 7-aryl- and 7-hetaryl-7-deazaadenosines were prepared by the cross-coupling reactions of unprotected or protected 7-iodo-7-deazaadenosines with (het)arylboronic acids, stannanes, or zinc halides. Nucleosides bearing 5-membered heterocycles at
- Bourderioux, Aurelie,Nau?, Petr,Perlíková, Pavla,Pohl, Radek,Pichová, Iva,Votruba, Ivan,D?ubák, Petr,Kone?ny, Petr,Hajdúch, Marián,Stray, Kirsten M.,Wang, Ting,Ray, Adrian S.,Feng, Joy Y.,Birkus, Gabriel,Cihlar, Tomas,Hocek, Michal
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supporting information; experimental part
p. 5498 - 5507
(2011/10/08)
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- First selective CYP11B1 inhibitors for the treatment of cortisol-dependent diseases
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Outgoing from an etomidate-based design concept, we succeeded in the development of a series of highly active and selective inhibitors of CYP11B1, the key enzyme of cortisol biosynthesis, as potential drugs for the treatment of Cushing's syndrome and rela
- Hille, Ulrike E.,Zimmer, Christina,Vock, Carsten A.,Hartmann, Rolf W.
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supporting information; experimental part
p. 2 - 6
(2011/04/17)
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- Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand
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A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).
- Zhou, Yirong,Gong, Yuefa
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experimental part
p. 6092 - 6099
(2011/11/29)
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- FRICTIONLESS MOLECULAR ROTARY MOTORS
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A rotaxane consisting of a cucurbituril and an uncharged guest molecule, having low or null affinity therebetween is provided as well as processes for providing the same. Various uses as energy converters (“frictionless” molecular motors), biochips and biosensors using the same are also provided.
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Page/Page column 28
(2010/02/17)
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- The role of fluorine substitution in biphenyl methylene imidazole-type CYP17 inhibitors for the treatment of prostate carcinoma
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It has been established that the growth of most prostate carcinomas depends on androgen stimulation. The inhibition of cytochrome P450-17 (CYP17) to block androgen biosynthesis is therefore regarded as a promising approach to therapy. Based on our previou
- Hu, Qingzhong,Negri, Matthias,Olgen, Sureyya,Hartmann, Rolf W.
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scheme or table
p. 899 - 910
(2011/02/23)
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- Tetrazoles: XLIV. Synthesis and chemical properties of 5-substituted 2-triphenylmethyltetrazoles
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Tritylation of tetrazole and its 5-substituted derivatives with triphenylmethyl chloride under conditions of phase-transfer catalysis regioselectively yields the corresponding 5-substituted 2-trityltetrazoles which can be used to protect N-H bonds in nitrogen-containing heterocycles and O-H bonds in primary alcohols. Thermolysis of 2-trityltetrazoles in benzonitrile leads to 3,6-disubstituted 1,2,4,5-tetrazines. Thermal transformation of the same compounds in dodecane follows a radically different mechanism, resulting in formation of difficultly accessible 8,8-diphenylheptafulvenes. The structure of the latter was proved by X-ray analysis.
- Myznikov,Artamonova,Bel'skii,Stash,Skvortsov,Koldobskii
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p. 1360 - 1369
(2007/10/03)
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- Preparation of phosphorothioate oligomers
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The present invention is directed to methods for solid phase nucleotide synthesis utilizing substituted imidazole catalysts.
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- Treatment of GLC1A glaucoma with non-steroidal glucocorticoid antagonists
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Compositions of non-steroidal glucocorticoid antagonists for treating GLC1A glaucoma and methods for their use are disclosed.
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- Preparation of phosphorothioate and boranophosphate oligomers
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Methods and intermediates for the preparation of oligomers containing diastereomerically enriched phosphorothioate and boranophosphate linkages are disclosed.
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- Radical cyclisation onto imidazoles and benzimidazoles
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New synthetic methodology has been developed for the synthesis of [1,2- a]fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(ω-alkyl) radicals are generated using Bu3SnH from N-(ω-phenylselanyl)alkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used at the leaving groups in the homolytic substitutions.
- Aldabbagh, Fawaz,Bowman, W. Russell
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p. 4109 - 4122
(2007/10/03)
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- Preparation of chiral phosphorothioate oligomers
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Methods and intermediates for the preparation of oligomers containing diastereomerically enriched phosphorothioate linkages are disclosed.
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- Synthesis of Aryl 2-(2-Imidazolyl)ethyl Ketones
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The Claisen-Schmidt condensation of 1-(triphennylmethyl)-2-imidazolecarboxaldehyde with acetophenones yielded 1-aryl-3-propen-1-ones 7.Selective catalytic hydrogenation over platinum of 7 furnished 1-aryl-3-(2-imidazolyl)
- Abdelaal, Salma M.,Kim, Jang-Woo,Bauer, Ludwig
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p. 903 - 906
(2007/10/02)
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- Remarkable Selectivity in the Reaction of 1-Trityl-2-lithioimidazoles with t-Butyl Halogenoacetates
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2-Lithio-1-triphenylmethylimidazoles react with t-butyl halogenoacetates to give a variety of products, the nature of which is cleanly determined by the halogen atom.With chloroacetate the products are chloromethyl ketones, while bromacetate gives di-t-butyl imidazolesuccinates, and iodoacetate yields iodoimidazoles.In each case 50percent of the parent triphenylmethylimidazole is recovered from the reaction.When the triphenylmethyl substituent is replaced by the N,N-dimethylsulfamoyl group, reaction with bromoacetate is suppressed, but t-butyl chloroacetate and iodoacetate again give chloroketones and aryl iodides respectively.
- Coutts, Ian G. C.,Jieng, Shende,Khandelwahl, Ghanshyam D.,Wood, Michael L.
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p. 857 - 860
(2007/10/02)
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- Synthesis and antifungal activity of a series of difluorotritylimidazoles
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1-[(2-Fluorophenyl)(4-fluorophenyl)phenylmethyl]-1H-imidazole (flutrimazole, UR-4056, CAS 119006-77-8) (15) was selected among a series of mono-, di- and trifluorotrityl-imidazole antifungal agents as the most potent fluorine containing analogue of clotrimazole.
- Bartroli,Alguero,Boncompte,Forn
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p. 832 - 835
(2007/10/02)
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- Synthese Stereoselective de la Girolline
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Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereomeric derivatives have been separated.The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose : this ose is condensed with formamidine acetate to obtain a 4(5)--imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.Key Words: girolline synthesis; 2-aminoimidazole; D(-)-arabinose; 4(5)imidazole; rhodium reduction.
- Ahond, Alain,Mourabit, Ali Al,Bedoya-Zurita, Manuel,Heng, Richard,Braga, Raquel Marques,et al.
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p. 4327 - 4346
(2007/10/02)
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- 5-(1-(IMIDAZOL)METHYL)-3,3-DISUBSTITUTED-2(3H)FURANONE DERIVATIVES
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Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: STR1 wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring;R 1 and R 2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C. sub.3-C 6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy;R. sub.3, R 4 and R 5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R 4 and R. sub.5 or R 3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R 1 and R 2 substituted benzyl or phenyl.R 6 in the dihydrofuranone series is hydrogen or lower alkyl.Also described are the pharmaceutically acceptable quaternary alkyl and acid addition salts of such compounds. The compounds are particularly useful in the treatment of neurogenic bladder disorder and chronic obstructive pulmonary diseases.
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- Electrophilic Reactivity of the Triphenylmethyl Carbocation in Aqueous Solutions
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The triphenylmethyl (trityl) carbocation has been generated as a transient intermediate by laser flash photolysis of 1:2 (v/v) acetonitrile:water solutions of trityl acetate and trityl 4-cyanophenyl ether.Identification of the transient as the free carbocation in the ground state was based on its characteristic absorption spectrum and upon conductivity changes.Rate constants have been measured for the reaction of the cation in this solvent with a series of ionic and neutral nucleophiles.The solvent rate constant at 20 deg C is 1.5 x 105 s-1.Azide ions reacts at 4.1 x 109 M-1s-1; the directly measured azide:water ratio is compared to literature values determined by product analysis.Chloride ion reacts at 2 x 106 M-1 s-1; with bromide the equilibrium addition can be observed with k(comb) = 5 x 106 M-1 s-1 and k(ion) for Ph3CBr = 8 x 105 s-1.Rate constants do not adhere to the N+ relationship.This predicts a slope of unity in a plot of log k(Ph3C+) vs.N+, with the better nucleophiles reacting at the 1010 encounter-controlled limit.Azide is the only nucleophile of those studied to approach this.Sulfite and thiolate ions, which are better N+ nucleophiles, react at 2-3 x 108 M-1s-1, while amines react in the 106-107 M-1s-1 range.The plot vs.N+ has a slope of 0.3-0.4.One explanation is that rate constants for the better nucleophiles do level, but this occurs considerably below the 1010 limit.Alternatively, the less than unit slope is real and this more reactive cation, in contrast to more stable analogues, is exhibiting selectivity.
- McClelland, Robert A.,Banait, Narinder,Steenken, Steen
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p. 7023 - 7027
(2007/10/02)
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- 4-Lithio-1-tritylimidazole as a Synthetic Intermediate. Synthesis of Imidazole-4-carboxaldehyde
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Reaction of 4-iodo-1-tritylimidazole with n-butyllithium at -79 deg, followed by rapid quenching of the reaction mixture with DMF, gives good yields of 1-tritylimidazole-4(5)-carboxaldehyde, the isolation of which demonstrates the intermediacy of 4-lithio-1-tritylimidazole.This species should be destabilized by repulsive interaction of the negative charge on C-4 with the adjacent lone pair electrons on N-3 (the ALP effect).The isolation of 1-tritylimidazole-4(5)-carboxaldehyde in good yield and the versatility of the aldehyde functionality make 4-lithio-1-tritylimidazole a useful synthetic intermediate.
- Kirk, Kenneth L.
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- SYNTHESIS BY PHASE TRANSFER CATALYSIS OF N-BENZYL, N-DIPHENYLMETHYL AND N-TRIPHENYLMETHYL AZOLES AND BENZAZOLES: PROTON NMR AND CHROMATOGRAPHIC DATA AS A TOOL FOR IDENTIFICATION
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Pyrazole, imidazole, 1,2,4-triazole, indazole and benzotriazole were alkylated under phase transfer catalysis (PTC) with benzyl-, diphenylmethyl- and trityl chloride.Alkylation occured only at the ring nitrogen atoms of the heterocycle, except for indazole in which substitution took also place at position 3.A systematic study of the N- and C-substituted derivatives by proton NMR and chromatographic techniques has been done.
- Claramunt, Rosa M.,Elguero, Jose,Garceran, Rafael
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p. 2895 - 2906
(2007/10/02)
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- New Synthesis of 2-Nitroimidazoles
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1-Triphenylmethylimidazoles are treated with n-butyllithium in tetrahydrofuran at 0 deg C to form the 2-lithio derivatives.The latter species react with n-propyl nitrate to give 1-trityl-2-nitroimidazoles which, after acid hydrolysis, provide the correspondine 2-nitroimidazoles. 2-Nitroimidazole was obtained from imidazole from overall yields of 27-35percent; 4-methyl-2-nitroimidazole was obtained in 40percent overall yield from 4-methylimidazole.Imidazole-4,5-dicarboxylic acid was converted, in several steps, to 1-tritylimidazole-4-methanil, and the latter compound was transformed into 2-nitroimidazole-4-methanol in an overall yield of 18percent.Protection of the hydroxymethyl function was found to be unnecessary during carbanion formation and nitration.Attempts to nitrate 1-methylimidazole or 1-methoxymethylimidazole by the same procedure failed.
- Davis, Dwight P.,Kirk, Kenneth L.,Cohen, Louis A.
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p. 253 - 256
(2007/10/02)
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- Process for preparing N-tritylimidazole compounds
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A process for preparing N-tritylimidazole compounds of the formula: STR1 by the reaction between a tritylcarbinol derivative of the formula: STR2 and an imidazole derivative of the formula: STR3 , characterized in that the reaction is effected in the presence of a phosphorus compound of the formula: STR4
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