192182-30-2Relevant academic research and scientific papers
Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate
Montgomery, Thomas D.,Nibbs, Antoinette E.,Zhu, Ye,Rawal, Viresh H.
, p. 3480 - 3483 (2014/07/21)
We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.
Chemoselective and enantioselective oxidation of indoles employing aspartyl peptide catalysts
Kolundzic, Filip,Noshi, Mohammad N.,Tjandra, Meiliana,Movassaghi, Mohammad,Miller, Scott J.
supporting information; experimental part, p. 9104 - 9111 (2011/08/04)
Catalytic enantioselective indole oxidation is a process of particular relevance to the chemistry of complex alkaloids, as it has been implicated in their biosynthesis. In the context of synthetic methodology, catalytic enantioselective indole oxidation allows a rapid and biomimetic entry into several classes of alkaloid natural products. Despite this potentially high utility in the total synthesis, reports of catalytic enantioselective indole oxidation remain sparse. Here we report a highly chemoselective catalytic system for the indole oxidation that delivers 3-hydroxy-indolenines with good chemical yields and moderate to high levels of enantio- and diastereoselectivity (up to 95:5 er and up to 92:8 dr). These results represent, to our knowledge, the most selective values yet reported in the literature for catalytic asymmetric indole oxidation. Furthermore, the utility of enantioenriched hydroxy-indolenines in stereospecific rearrangements is demonstrated.
Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives
Movassaghi, Mohammad,Schmidt, Michael A.,Ashenhurst, James A.
supporting information; experimental part, p. 4009 - 4012 (2009/06/06)
(Chemical Equation Presented) The oxidation of 2-aryl tryptamines followed by a stereoselective rearrangement provides a versatile strategy for the synthesis of CS-quaternary oxindoles bearing a C3-aryl group. Treatment of optically active 2-aryl hydroxyindolenines with scandium trifluoromethanesulfonate in toluene at 110 °C leads to complete and stereoselective isomerization to the corresponding C3-aryl oxindoles which represent versatile intermediates for the synthesis of C3a-aryl hexahydropyrroloindoles.
Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase
Weinstein, David S.,Liu, Wen,Gu, Zhengxiang,Langevine, Charles,Ngu, Khehyong,Fadnis, Leena,Combs, Donald W.,Sitkoff, Doree,Ahmad, Saleem,Zhuang, Shaobin,Chen, Xing,Wang, Feng-Lai,Loughney, Deborah A.,Atwal, Karnail S.,Zahler, Robert,Macor, John E.,Madsen, Cort S.,Murugesan, Natesan
, p. 1435 - 1440 (2007/10/03)
A series of inhibitors of mammalian 15-lipoxygenase based on tryptamine and homotryptamine scaffolds is described. Compounds with aryl substituents at C-2 of the indole core of tryptamine and homotryptamine sulfonamides (e.g., 37a-p) proved to be potent i
Initial structure-activity relationship of a novel class of nonpeptidyl GnRH receptor antagonists: 2-arylindoles
Chu, Lin,Hutchins, Jennifer E.,Weber, Ann E.,Lo, Jane-Ling,Yang, Yi-Tien,Cheng, Kang,Smith, Roy G.,Fisher, Michael H.,Wyvratt, Matthew J.,Goulet, Mark T.
, p. 509 - 513 (2007/10/03)
A nonpeptidyl GnRH receptor antagonist (1), with a unique 2-arylindole core, was identified through the Merck in-house screening for binding affinity on the rat GnRH receptor. SAR studies directed toward the alkoxy-ethanolamine and 2-aryl groups resulted in a simpler lead structure with improved activity. This compound 50 exhibits a 60-fold improvement in binding activity over our initial lead 1.
Studies on the novel anti-staphyloccal compound nematophin
Kennedy, Gordon,Viziano, Monica,Winders, John Alexander,Cavallini, Palmina,Gevi, Monica,Micheli, Fabrizio,Rodegher, Pamela,Seneci, Pierfausto,Zumerle, Aurelia
, p. 1751 - 1754 (2007/10/03)
A number of analogues of the recently described compound nematophin were prepared and studied for antibacterial activity. The 2-phenyl derivative was found to exhibit exceptional activity against methicillin resistant Staphylococcus aureus (MRSA) whereas the isosteric benzimidazole analogue was much less active. (C) 2000 Elsevier Science Ltd. All rights reserved.
Synthesis of 2-aryltryptamines with palladium catalyzed cross-coupling of 2-bromotryptamines and arylboronic acids
Chu, Lin,Fisher, Michael H.,Goulet, Mark T.,Wyvratt, Matthew J.
, p. 3871 - 3874 (2007/10/03)
A versatile and high-yielding synthesis of 2-aryltryptamines employing palladium(0) catalyzed cross-coupling of 2-bromotryptamines and arylboronic acids was developed. The preparation of the intermediate 2-bromotryptamines with pyridine hydrobromide perbromide as the brominating agent, is also reported.
