- Synthetic method of 4-hydroxyindole
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The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of 4-hydroxyindole. Aiming at the problems existing in industrial production of 4-hydroxyindole in the prior art, the technical scheme of the invention is as follows: the method comprises the following steps: (1) protecting hydroxyl in a compound 3 by using a protective group to obtaina compound 4; (2) reacting the compound 4 with N, N-dimethylformamide dimethyl acetal to obtain a compound 5; (3) mixing the compound 5 with NH2NH2.H2O and MeOH, and carrying out a reaction to obtaina compound 6; and (4) removing the protective group of the compound 6 to obtain 4-hydroxyindole. According to the method for synthesizing 4-hydroxyindole, the cost of starting materials is low, the reaction conditions in the synthesis process are mild, operation is convenient, aftertreatment is simple, and the yield is high.
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Paragraph 0039; 0043-0050
(2021/03/30)
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- Aryl Substituted Benzimidazolones as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors
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Since the discovery of HIV as the etiological agent of AIDS, the virus has infected millions of people each year. Fortunately, with the use of HAART, viremia can be suppressed to below detectable levels in the infected individuals, which significantly improves their quality of life and prevents the onset of AIDS. However, HAART is not curative and issues relating to adherence and drug resistance may lead to the re-emergence of viremia, the development of AIDS, and ultimately death. To address a pressing need for the development of new and efficacious antiretroviral agents with activity against viruses bearing prevalent resistant mutations, we have designed two generations of benzimidazolone derivatives as HIV non-nucleoside reverse transcriptase inhibitors. The first generation benzimidazolone inhibitors were found to be potent inhibitors of wild-type HIV reverse transcriptase but were ineffective in the presence of common resistance mutations such as K103N and Y181C. A second generation benzimidazolone inhibitor (compound 42) not only showed inhibitory activity against wild-type HIV but also remained active against HIV containing the K103N, Y181C, and K103N/Y181C drug resistance mutations.
- Pribut, Nicole,Basson, Adriaan E.,Van Otterlo, Willem A. L.,Liotta, Dennis C.,Pelly, Stephen C.
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supporting information
p. 196 - 202
(2019/02/05)
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- Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors
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Since Hsp90 modulates all six hallmarks of cancer simultaneously, it has become an attractive target for the development of cancer chemotherapeutics. In an effort to develop more efficacious compounds for Hsp90 inhibition, novobiocin analogues were prepared by replacing the central coumarin core with naphthalene, quinolinone, and quinoline surrogates. These modifications allowed for modification of the 2-position, which was previously unexplored. Biological evaluation of these compounds suggests a hydrophobic pocket about the 2-position of novobiocin. Anti-proliferative activities of these analogues against multiple cancer cell lines identified 2-alkoxyquinoline derivatives to exhibit improved activity.
- Kusuma, Bhaskar Reddy,Khandelwal, Anuj,Gu, Wen,Brown, Douglas,Liu, Weiya,Vielhauer, George,Holzbeierlein, Jeffrey,Blagg, Brian S.J.
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supporting information
p. 1441 - 1449
(2014/03/21)
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- IMIDAZOLIDINEDIONE DERIVATIVES
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The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.
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Page/Page column 61
(2011/06/26)
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- Structure-activity relationships in the acronycine and benzo[b]acronycine series: Role of the pyran ring
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In order to explore the structure-activity relationships in the acronycine series, simplified analogues of cis-1,2-diacetoxy-1,2-dihydroacronycine and cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1, under clinical trials) lacking the fused pyran ring, but possessing an acetoxymethyl leaving group at position 4 were prepared. These new analogues only displayed marginal antiproliferative activity compared to the parent compounds. The presence of the angularly fused dimethylpyran ring appears as an indispensable structural requirement to observe significant cytotoxic activity in this series.
- Do, Quyen,Thi Mai, Huong Doan,Gaslonde, Thomas,Pfeiffer, Bruno,Leonce, Stephane,Pierre, Alain,Michel, Sylvie,Tillequin, Francois,Dufat, Hanh
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scheme or table
p. 2677 - 2687
(2009/04/11)
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- SYNTHESIS OF 4-SUBSTITUTED INDOLES FROM o-NITROTOLUENES
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A facile two- or three-step transformation of o-nitrotoluenes into 4-substituted indoles is described.Treatment of o-nitrotoluenes 1 with DMF acetal, or sometimes more advantageously with tris(N,N-dimethylamino)methane, affords β-(N,N-dimethylamino)styrenes 2 which are readily converted too-nitrophenylacetaldehyde semicarbazones 3 without isolation.Reduction of either 2 or 3 affords 4-substituted indoles 4.Use of the very insoluble semicarbazones results in vastly superior yields of 4 by minimizing completing bimolecular condensation reactions during reduction.This new procedure has been applied to efficiently and conveniently prepare a series of 4-substituted indoles 4.
- Kruse, Lawrence I.
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p. 1119 - 1124
(2007/10/02)
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