129150-68-1Relevant articles and documents
5-Alkyloxytryptamines are membrane-targeting, broad-spectrum antibiotics
Faulkner, Katherine C.,Hurley, Katherine A.,Weibel, Douglas B.
, p. 5539 - 5544 (2016)
Antibiotic adjuvant therapy represents an exciting opportunity to enhance the activity of clinical antibiotics by co-dosing with a secondary small molecule. Successful adjuvants decrease the concentration of antibiotics used to defeat bacteria, increase activity (in some cases introducing activity against organisms that are drug resistant), and reduce the frequency at which drug-resistant bacteria emerge. We report that 5-alkyloxytryptamines are a new class of broad-spectrum antibacterial agents with exciting activity as antibiotic adjuvants. We synthesized 5-alkyloxytryptamine analogs and found that an alkyl chain length of 6–12 carbons and a primary ammonium group are necessary for the antibacterial activity of the compounds, and an alkyl chain length of 6–10 carbons increased the membrane permeability of Gram-positive and Gram-negative bacteria. Although several of the most potent analogs also have activity against the membranes of human embryonic kidney cells, we demonstrate that below the minimum inhibitory concentration (MIC)—where mammalian cell toxicity is low—these compounds may be successfully used as adjuvants for chloramphenicol, tetracycline, ciprofloxacin, and rifampicin against clinical strains of Salmonella typhimurium, Acinetobacter baumannii and Staphylococcus aureus, reducing MIC values by as much as several logs.
Highly fluorescent one-handed nanotubes assembled from a chiral asymmetric perylene diimide
Ma, Xiaojie,Zhang, Yibin,Zheng, Yingxuan,Zhang, Yifan,Tao, Xia,Che, Yanke,Zhao, Jincai
, p. 4231 - 4233 (2015)
Highly fluorescent bilayer nanotubes with a right- or left-handed helical sense were assembled from a chiral asymmetric perylene diimide for the first time, which constitute a new family member of self-assembled organic nanotubes.
Chirality Inversion in Self-Assembled Nanocomposites Directed by Curvature-Mediated Interactions
Cao, Zhaozhen,Gong, Yanjun,Liu, Rongjuan,Wei, Jingjing,Yang, Zhijie,Zhang, Fenghua,Zhang, Zongze
, (2022/01/20)
Nanoscale curvature-dependent interactions are of paramount importance in biological systems. Here, we report that nanoscale curvature plays an important role in regulating the chirality of self-assembled nanocomposites from chiral organic molecules and achiral nanoparticles. Specifically, we show that the supramolecular chirality of the nanocomposites markedly depends on the nanoparticle curvature, where small-sized nanoparticles of high curvature and large-sized nanoparticles of low curvature lead to nanocomposites with opposite chirality. Quantitative kinetic experiments and molecular dynamics simulations reveal that nanoparticle curvature plays a key role in promoting the pre-nucleation oligomerization of chiral molecules, which consequently regulates the supramolecular chirality of the nanocomposites. We anticipate that this study will aid in rational design of an artificial cooperative system giving rise to emergent assembling phenomena that can be surprisingly rich and often cannot be understood by studying the conventional noncooperative systems.
Catalytic Strategy for Regioselective Arylethylamine Synthesis
Boyington, Allyson J.,Seath, Ciaran P.,Zearfoss, Avery M.,Xu, Zihao,Jui, Nathan T.
supporting information, p. 4147 - 4153 (2019/03/07)
A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.
NEW CYCLOHEXYL AND QUINUCLIDINYL CARBAMATE DERIVATIVES HAVING BETA2 ADRENERGIC AGONIST AND M3 MUSCARINIC ANTAGONIST ACTIVITY
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Page/Page column 70, (2014/07/08)
The present invention relates to novel compounds having β2 adrenergic agonist and M3 muscarinic antagonist dual activity, to pharmaceutical compositions containing them, to the process for their preparation and to their use in respiratory therapies.
Diverse alkaloid-like structures from a common building block
Goff, Dane A.
, p. 242 - 256 (2013/01/15)
A wealth of unique enantiopure polycyclic alkaloid-like scaffolds can be prepared on a multigram scale in only a few steps from a common, commercially available intermediate. The attached nitromethyl group can then be used to construct highly diverse func
SYNTHESIS OF POLYCYCLIC ALKALOIDS
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Paragraph 0214, (2013/09/26)
Disclosed embodiments concern polycyclic alkaloid compounds and methods for their use and synthesis. Particular embodiments concern polycyclic alkaloids having a fused, six-membered ring, while other embodiments concern polycyclic alkaloids having a fused
Synthesis and structure activity relationship of tetrahydroisoquinoline- based potentiators of GluN2C and GluN2D containing N-Methyl-D-aspartate receptors
Santangelo Freel, Rose M.,Ogden, Kevin K.,Strong, Katie L.,Khatri, Alpa,Chepiga, Kathryn M.,Jensen, Henrik S.,Traynelis, Stephen F.,Liotta, Dennis C.
, p. 5351 - 5381 (2013/07/26)
We describe here the synthesis and evaluation of a series of tetrahydroisoquinolines that show subunit-selective potentiation of NMDA receptors containing the GluN2C or GluN2D subunits. Bischler-Napieralski conditions were employed in the key step for the
SUBSTITUTED 2-[2-(PHENYL) ETHYLAMINO] ALKANEAMIDE DERIVATIVES AND THEIR USE AS SODIUM AND/OR CALCIUM CHANNEL MODULATORS
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Page/Page column 14, (2010/08/22)
Substituted 2-[2-(phenyl)ethylamino]alkaneamide derivatives, pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing them are useful as sodium and/or calcium channel modulators for preventing, alleviating and curing pathologi
DERIVATIVES OF 4-(2-AMINO-1-HYDROXYETHYL)PHENOL AS AGONISTS OF THE BETA2 ADRENERGIC RECEPTOR
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Page/Page column 28, (2009/07/03)
The present invention provides a compound of formula (I): wherein: ? R1 is a group selected from -CH2OH,-NH(CO)H and ? R2 is a hydrogen atom; or ? R1together with R2 form the group -NH-C(O)-CH=CH-, wherein the nitrogen atom is bound to the carbon atom in the phenyl ring holding R1and the carbon atom is bound to the carbon atom in the phenyl ring holding R2 ? R3a and R3bare independently selected from the group consisting of hydrogen atoms and C1-4alkyl groups, ? n represents an integer from 1 to 3; ? Ad represents 1-adamantyl or 2-adamantyl group, or a pharmaceutically-acceptable salt or solvate or stereoisomer thereof.