453-71-4Relevant academic research and scientific papers
Substituent effects on the isomerization of hydrazone switches driven by the intramolecular hydrogen bond
Lu, Chaocao,Htan, Bu,Fu, Shitao,Ma, Chunmiao,Gan, Quan
, p. 4010 - 4016 (2019/07/03)
In this work, the substituent effects on hydrogen bonding in one kind of hydrazone-based switch are revealed. The E/Z isomerization ratios of these hydrazones and their intramolecular hydrogen bond strengths in the Z form were evaluated using NMR technique. Linear correlations between these parameters and Hammett empirical values for substituent effects are explored as well.
Synthesis of a secretoglobin 3A2 type C (98–139) fragment by Dawson's native chemical ligation
Kikuchi, Mariko,Kurotani, Reiko,Konno, Hiroyuki
supporting information, p. 4145 - 4148 (2017/09/29)
A secretoglobin 3A2 type C (98–139) peptide was synthesized by native chemical ligation between 115Ile and 116Cys residues using Dawson's linker. The peptide-N-acyl-benzimidazolinone-glycine amide, a C-terminal thioesters precursor, was provided from 3-amino-4-(methylamino)benzoic acid. In addition, an N-terminal cysteine fragment, the (116–139) peptide, was prepared by ordinary Fmoc-solid phase peptide synthesis. Native chemical ligation of the (98–115) fragment with the Dawson's linker and the (116–139) peptide smoothly proceeded to give SCGB3A2 type C (98–139) peptide.
IMINOTETRAHYDROPYRIMIDINONE DERIVATIVES AS PLASMEPSIN V INHIBITORS
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Page/Page column 53, (2017/07/05)
A series of 2-imino-6-methyltetrahydropyrimidin-4(lH)-one derivatives, substituted in the 6-position by a phenyl moiety which in turn is meta-substituted by an optionally substituted unsaturated fused bicyclic ring system containing at least one nitrogen atom, being selective inhibitors of plasmepsin V activity, are beneficial as pharmaceutical agents, especially in the treatment of malaria.
A one-pot synthesis of tetrazolones from acid chlorides: Understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs
Duncton, Matthew A. J.,Singh, Rajinder
supporting information, p. 9338 - 9342 (2016/10/13)
A one-pot and scalable synthesis of tetrazolones (tetrazol-5-ones) from acid chlorides using azidotrimethylsilane is presented. The reaction tolerates many functional groups and can furnish aryl-, heteroaryl-, alkenyl-, or alkyl-substituted tetrazolone products in moderate to excellent yield (14-94%). No reduction in yield was observed when the reaction was undertaken on a larger-scale (20-36 g). The method could be used for the late-stage functionalization of pharmaceuticals, to provide tetrazolone congeners of the marketed drugs aspirin, indomethacin, probenecid, telmisartan, bexarotene, niacin (vitamin B3), and the active metabolite of the recently-launched immuno-modulatory agent, BG-12 (Tecfidera). The ability of a tetrazolone group to serve as a bioisostere of a carboxylic acid, and to improve drug pharmacokinetic profiles is also highlighted.
Stable and easily accessible functional dyes: Dihydrotetraazaanthracenes as versatile precursors for higher acenes
Gampe, Dominique Mario,Kaufmann, Martin,Jakobi, D?rthe,Sachse, Torsten,Presselt, Martin,Beckert, Rainer,G?rls, Helmar
, p. 7571 - 7581 (2015/05/13)
Abstract A series of new dihydrotetraazaanthracenes and one new dihydrotetraazatetracene as substances for applications in organoelectronic devices and as suitable building blocks for higher azaacenes was synthesised. The condensation of aromatic diamines with dichlorodicyanopyrazine led to these tricyclic/tetracyclic compounds. Syntheses of N-substituted phenylenediamines were developed to enable the introduction of multiple functional groups such as ester, amino, or nitro groups on the chromophoric system. Relationships between the structure and the spectroscopic properties could be derived from UV/Vis absorption and fluorescence spectroscopy, as well as by DFT and TD-DFT calculations of molecular and aggregate structures. The absorption spectra are dominated by π-π transitions of the single molecules, whereas aggregation needs to be taken into account to obtain reasonable agreement between theory and experiment in certain cases. Single-crystal X-ray analyses were carried out to examine the morphology and solid packing effects. Finally, a dihydrotetraazaanthracene was used as a building-block to create a mesoionic octaazapentacene. Dihydroazaacenes: A series of dihydrotetraazaanthracenes and one new dihydrotetraazatetracene as substances for applications in organoelectronic devices and as suitable building blocks for higher azaacenes was synthesised. Single-crystal X-ray analyses were carried out to examine the morphology and solid packing effects. Finally, a dihydrotetraazaanthracene was used as a building-block to create a mesoionic octaazapentacene.
Aromatic triazole foldamers induced by C-H...X (X = F, Cl) intramolecular hydrogen bonding
Shang, Jie,Gallagher, Nolan M.,Bie, Fusheng,Li, Qiaolian,Che, Yanke,Wang, Ying,Jiang, Hua
, p. 5134 - 5144 (2014/06/23)
Aryl-triazole oligomers based on isobutyl 4-fluorobenzoate and isobutyl 4-chlorobenzoate were designed and synthesized. Crystal structure and 1H-1H NOESY experiments demonstrate that the oligomers adopt stable helical conformation, which are induced by C5-H...X-C (X = F, Cl) intramolecular hydrogen bonding between triazole protons and halogen atoms. The stabilities of the folded conformations are confirmed by DFT calculations, which show that each C5-H...F-C planar interaction lowers the energy by ～3 kcal mol-1 on average, and by ～1 kcal mol-1 when C5-H...Cl-C bridges are formed. The hydrogen-bonding networks are disrupted in competitive hydrogen-bonding media such as DMSO, generating the unfolded oligomers.
INDOLE COMPOUNDS OR ANALOGUES THEREOF USEFUL FOR THE TREATMENT OF AGE-RELATED MACULAR DEGENERATION (AMD)
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Page/Page column 240-241, (2012/07/27)
The present invention provides a compound of formula (I): a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
Cycloalkylated benzothiadiazines, a process for their preparation and pharmaceutical compostions containing them
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Page/Page column 22-23, (2010/02/17)
Compounds of formula (I): wherein: RCy represents an unsubstituted or substituted cycloalkyl group or cycloalkylalkyl group,R1, R2, R3 and R4, which may be the same or different, each represent a hydrogen or halogen atom or a nitro group; a cyano group; a hydroxy group; an alkoxy group; an alkyl group; an unsubstituted or substituted amino group; a carboxy group; an alkoxycarbonyl group; an aryloxycarbonyl group; an unsubstituted or substituted aminocarbonyl group. Medicinal products containing the same which are useful in treating or preventing conditions treatable by an AMPA receptor modulator.
INHIBITORS OF STEAROYL-COA DESATURASE
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, (2009/06/27)
Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.
BENZOIMIDAZOLE, TETRAHYDRO-QUINOXALINE, BENZOTRIAZOLE, DIHYDRO-IMIDAZO[4,5-c] PYRIDINONE AND DIHYDRO-ISOINDOLONE DERIVATIVES
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Page/Page column 20, (2008/12/08)
This invention relates to compounds of the formula wherein A, R1 to R3 are as defined in the specification and G is benzoimidazole, quinoxaline, benzotriazole, dihydro-imidazo[4,5-c]pyridine and dihydro-isoindolone group as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
