908295-26-1Relevant articles and documents
5-Nitroindole oligonucleotides with alkynyl side chains: Universal base pairing, triple bond hydration and properties of pyrene "click" adducts
Ingale, Sachin A.,Leonard, Peter,Yang, Haozhe,Seela, Frank
, p. 8519 - 8532 (2014)
Oligonucleotides with 3-ethynyl-5-nitroindole and 3-octadiynyl-5-nitroindole 2′-deoxyribonucleosides were prepared by solid-phase synthesis. To this end, nucleoside phosphoramidites with clickable side chains were synthesized. The 3-ethynylated 5-nitroindole nucleoside was hydrated during automatized DNA synthesis to 3-acetyl-5-nitroindole 2′-deoxyribonucleoside. Side product formation was circumvented by triisopropylsilyl protection of the ethynyl side chain and was removed with TBAF after oligonucleotide synthesis. All compounds with a clickable 5-nitroindole skeleton show universal base pairing and can be functionalized with almost any azide in any position of the DNA chain. Functionalization of the side chain with 1-azidomethylpyrene afforded click adducts in which the fluorescence was quenched by the 5-nitroindole moieties. However, fluorescence was slightly recovered during duplex formation. Oligonucleotides with a pyrene residue and a long linker arm are stabilized over those with non-functionalized side chains. From the UV red shift of the pyrene residue in oligonucleotides and modelling studies, pyrene intercalation was established for the long linker adduct showing increased duplex stability over those with a short side chain. This journal is
Facile synthesis of isatins by direct oxidation of indoles and 3-iodoindoles using NIS/IBX
Chandra, Ajeet,Yadav, Navin R.,Moorthy, Jarugu Narasimha
supporting information, p. 2169 - 2174 (2019/03/04)
A facile one-pot access to a broad range of isatins by direct oxidation of indoles using NIS/IBX reagent in DMSO at 25 °C in very good isolated yields is reported. It is shown by mechanistic investigations that a number of substituted indoles react rapidly with NIS in DMSO to produce intermediary 3-iodoindoles, which undergo oxidation subsequently to isatins with IBX.
PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives
Himabindu, Vittam,Parvathaneni, Sai Prathima,Rao, Vaidya Jayathirtha
, p. 18889 - 18893 (2018/11/27)
This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.
Construction of Cyclopenta[b]indol-1-ones by a Tandem Gold(I)-Catalyzed Rearrangement/Nazarov Reaction and Application to the Synthesis of Bruceolline H
Scarpi, Dina,Petrovi?, Martina,Fiser, Béla,Gómez-Bengoa, Enrique,Occhiato, Ernesto G.
supporting information, p. 3922 - 3925 (2016/08/16)
A tandem gold(I)-catalyzed rearrangement/Nazarov reaction of enynyl acetates which efficiently provides cyclopenta[b]indol-1-ones as useful precursors for the synthesis of natural and bioactive compounds is described. The synthetic potential of the method
Synthesis of isatins by I2/TBHP mediated oxidation of indoles
Zi, You,Cai, Zhong-Jian,Wang, Shun-Yi,Ji, Shun-Jun
supporting information, p. 3094 - 3097 (2014/06/23)
An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.
NON-NATURAL NUCLEOSIDES AS THERANOSTIC AGENTS
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Paragraph 00134, (2013/03/28)
A theranostic agent for inhibiting translesion DNA replication comprises natural adenine ribose analog having formula I.
Cu-catalyzed synthesis of tryptanthrin derivatives from substituted indoles
Wang, Chen,Zhang, Lianpeng,Ren, Anni,Lu, Ping,Wang, Yanguang
supporting information, p. 2982 - 2985 (2013/07/26)
A concise method for the preparation of tryptanthrins from indoles via the copper-catalyzed aerobic oxidation is described. The reactions can be carried out under mild reaction conditions with varying functional group tolerance.
Amino-zinc-ene-enolate cyclization: A short access to cis-3-substituted prolino-homotryptophane derivatives
Mothes, Celine,Lavielle, Solange,Karoyan, Philippe
, p. 6706 - 6710 (2008/12/22)
(Chemical Equation Presented) Proline chimeras are useful tools for medicinal chemistry and/or biological applications. The asymmetric synthesis of cis-3-substituted prolines can be easily achieved via amino-zinc-ene-enolate cyclization followed by transm
Mild and efficient iodination of aromatic and heterocyclic compounds with the NaClO2/NaI/HCl system
Lista, Liliana,Pezzella, Alessandro,Napolitano, Alessandra,d'Ischia, Marco
, p. 234 - 239 (2008/09/16)
NaClO2/NaI in the presence of HCl is a mild, cheap, and non-toxic reagent for the iodination of phenols, including estradiol and naphthol, aromatic amines, and heterocyclic substrates, e.g., indoles, 8-hydroxyquinoline, imidazole, in fair to excellent yields by a very simple isolation protocol. The scope of the procedure is exemplified by the first iodination of 5-nitroindole to 3-iodo-5-nitroindole in 75% yield.
Labeling reagent
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, (2008/06/13)
The current invention restates substituted indole nucleosides as both terminal as well as internal building blocks of labeled oligonucleotide probes for the detection, analysis and quantitation of nucleic acids. The substituent comprises a linker and a de
