- Discovery of benzimidazole analogs as a novel interleukin-5 inhibitors
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A series of novel hydroxyethylaminomethylbenzimidazole analogs 5a-y were synthesized and evaluated for their IL-5 inhibitory activity using pro-B Y16 cell line. Among them, 2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino)butan-1-ol (5e, 94.3% inhibition at 30 μM, IC50 = 3.5 μM, cLogP = 4.132) and 3-cyclohexyl-2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino) propan-1-ol (5k, 94.7% inhibition at 30 μM, IC50 = 5.0 μM, cLogP = 6.253) showed the most potent inhibitory activity. The essential feature of SAR (Fig. 5) indicated that the chromenone ring can be replaced by a benzimidazole ring to maintain the inhibitory activity. In addition, the hydroxyethylaminomethyl group was suitable for the IL-5 inhibitory activity. Moreover, the hydrophobic substituents on carbon play an important role in the IL-5 inhibitory activity of these analogs. However, N-substituted analogs did not improve inhibitory activity. In addition, MTT assay of 5e and 5k with normal B lymphoblasts revealed that they had no significant effects on cell viability.
- Boggu, Pulla Reddy,Kim, Youngsoo,Jung, Sang-Hun
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- Synthesis of new 3-substituted 1,3-oxazolidine-2-thiones
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Reaction of N-alkylsubstituted ethanolamines with carbon disulfide followed by reaction with benzoyl chloride afforded N-substituted oxazolidine-2-thiones.
- Takibayeva,Ibraev,Kabieva
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p. 1310 - 1312
(2017/08/08)
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- METHOD FOR PRODUCING CIS- AND TRANS-ENRICHED MDACH
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A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.
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- N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst
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Abstract: The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction. Graphical Abstract: A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.[Figure not available: see fulltext.]
- Chen, Aimin,Wang, Houyong,Liu, Rui,Bo, Yingying,Hu, Jun
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p. 1182 - 1193
(2016/07/06)
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- Pyrithione biocides enhanced by zinc metal ions and organic amines
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The present invention is directed to a stable, soluble, antimicrobial composition concentrate comprising pyrithione or a pyrithione complex in an amount of from about 0.5% to about 30 weight percent, a zinc source in an amount of from about 0.1% to about 10%, and an organic amine component in an amount of from about 30% to about 80%, said percents being based upon the total weight of the composition concentrate. The invention is also directed to methods of controlling the growth of free-living microorganisms or biofilms using the antimicrobial composition of the invention, and products made using the antimicrobial composition of the invention.
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- Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
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This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- Acid-Catalyzed Decomposition of 1-Alkyltriazolines: A Mechanistic Study
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1-Alkyltriazolines are five-membered cyclic triazenes containing the unusual Z-configuration for the triazene moiety.The hydrolytic decomposition of these compounds in aqueous or mixed acetonitrile-aqueous buffers leads predominantly to the formation of the corresponding 1-alkylaziridines and lesser amounts of 2-(alkylamino)ethanols, alkylamines, and acetaldehyde.The latter two products presumably result from hydrolysis of a rearrangement produkt, N-ethylidenealkylamine.Neither the nature of the 1-alkyl group nor the pH of the medium greatly influences the product distribution, although decomposition in purely aqueous buffers slightly reduces the aziridine yields.The rate of hydrolysis of 1-alkyltriazolines is about twice as fast as that of the analogous acyclic 1,3,3-trialkyltriazenes and varies in the order tert-butyl > isopropyl > ethyl > butyl > methyl > propyl > benzyl.The mechanism of the decomposition is specific acid-catalyzed (A1) involving rapid reversible protonation followed by rate-limiting formation of a 2-(alkylamino)ethyldiazonium ion.The slopes of the log kobs versus pH plots are near -1.0.The solvent deuterium isotope effect, kH2O/kD2O, is in all cases methyl > ethyl.
- Smith, Richard H.,Wladkowski, Brian D.,Taylor, Jesse E.,Thompson, Erin J.,Pruski, Brunon,et al.
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p. 2097 - 2103
(2007/10/02)
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- The selective preparation of n-propylamines by the rhodium catalysed reaction of ethylene and syngas with alkylamines
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The aminoethylation of ethylene with a primary amine has been shown to provide a highly selective route to n-propylamines; the rhodium catalysed reaction of n-propylamine with ethylene and syngas (2/1, H2/CO) affords di-n-propylamine with 98percent selectivity (with respect to ethylene).The reaction of amines of the type RR1NH with the ethylene/syngas mixture and a rhodium catalyst provides a highly selective and general route to the n-propylamines RR1NPr (R=Pr, R1=H; R=t-Bu, R1=H; R=n-Bu, R1=H; R=C8H17, R1=H, R=R1=Pr; R=HOCH2Ch2, R1=H, and R=PhCH(OH)CH2, R1=H).
- Jones, M. D.
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p. 403 - 408
(2007/10/02)
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