- Concerning the preparation of 6-bromotryptamine
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Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.
- Scott Wiens,Johnson, Jerry L.,Gribble, Gordon W.
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- Rationally designed N-phenylsulfonylindoles as a tool for the analysis of the non-basic 5-HT6R ligands binding mode
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Among all of the monoaminergic receptors, the 5-HT6R has the highest number of non-basic ligands (approximately 5% of compounds stored in 25th version of ChEMBL database have the strongest basic pKa below 5, calculated using the Instant JChem c
- Staroń, Jakub,Bugno, Ryszard,Pietru?, Wojciech,Sata?a, Grzegorz,Mordalski, Stefan,Warszycki, Dawid,Hogendorf, Agata,Hogendorf, Adam S.,Kalinowska-T?u?cik, Justyna,Lenda, Tomasz,Pilarski, Bogus?aw,Bojarski, Andrzej J.
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supporting information
(2020/10/26)
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- Construction of Oxepino[3,2-b]indoles via [4+3] Annulation of 2-Ylideneoxindoles with Crotonate-Derived Sulfur Ylides
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A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate to excellent yields (62-93%) under mild conditions. Moreover, the synthetic oxepino[3,2-b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF-7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively. (Figure presented.).
- Fei, Xing-Hai,Guan, Xiang,He, Bin,Li, Zong-Qin,Wang, Da-Peng,Yang, Fen-Fen,Yang, Yuan-Yong,Zhao, Yong-Long,Zhou, Meng
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supporting information
p. 3018 - 3024
(2021/06/26)
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- Asymmetric Construction of 4 H-Pyrano[3,2-b]indoles via Cinchonine-Catalyzed 1,4-Addition of 2-Ylideneoxindole with Malononitrile
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A highly enantioselective [4 + 2] annulation of 2-ylideneoxindole with malononitrile has been accomplished by cinchonine catalysis under mild conditions. The corresponding enantiomerically enriched 4H-pyrano[3,2-b]indoles were generated in moderate to hig
- Zhou, Jin,Wang, Biao,He, Xiang-Hong,Liu, Li,Wu, Jun,Lu, Jing,Peng, Cheng,Rao, Chao-Long,Han, Bo
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p. 5450 - 5459
(2019/04/25)
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- Highly diastereoselective synthesis of cyclopropane-fused spiro-pseudoindoxyl derivatives through [2 + 1] annulation of 2-ylideneoxindoles and sulfonium bromides
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Compared with the intensively studied C3 spirooxindoles, limited reliable approaches are reported for synthesizing structurally analogous C2-spiropseudoindoxyl derivatives. Here, we developed an efficient method for highly diastereoselective synthesis of
- Tang, Xue,Zhu, Hong-Ping,Zhou, Jin,Chen, Yang,Pan, Xiao-Li,Guo, Li,Li, Jun-Long,Peng, Cheng,Huang, Wei
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supporting information
p. 8169 - 8174
(2018/11/23)
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- Discovery and optimization of a new class of pyruvate kinase inhibitors as potential therapeutics for the treatment of methicillin-resistant Staphylococcus aureus infections
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A novel series of bis-indoles derived from naturally occurring marine alkaloid 4 were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK is not only critical for bacterial survival which
- Kumar, Nag S.,Dullaghan, Edie M.,Finlay, B. Brett,Gong, Huansheng,Reiner, Neil E.,Jon Paul Selvam,Thorson, Lisa M.,Campbell, Sara,Vitko, Nicholas,Richardson, Anthony R.,Zoraghi, Roya,Young, Robert N.
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p. 1708 - 1725
(2014/03/21)
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- Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
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The sulfonation of various 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile has been studied, leading to the development of a clean and operationally simple protocol allowing direct synthesis of the corresponding 1-phenylsulfonyl-1H-pyrrole-3- sulfonyl chlorides and 1-phenylsulfonyl-1H-indole-3-sulfonyl chlorides, respectively, both of which may be easily converted to various sulfonamide derivatives by treatment with nitrogen nucleophiles. Efficient and selective removal of the phenylsulfonyl- or tosyl groups in the sulfonamide series may be achieved under mild conditions.
- Janosik, Tomasz,Shirani, Hamid,Wahlstr?m, Niklas,Malky, Ilham,Stensland, Birgitta,Bergman, Jan
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p. 1699 - 1707
(2007/10/03)
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