- 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; 0051-0058
(2021/03/30)
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- Cell-Based Optimization of Covalent Reversible Ketoamide Inhibitors Bridging the Unprimed to the Primed Site of the Proteasome β5 Subunit
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The ubiquitin-proteasome system (UPS) is an established therapeutic target for approved drugs to treat selected hematologic malignancies. While drug discovery targeting the UPS focuses on irreversibly binding epoxyketones and slowly-reversibly binding boronates, optimization of novel covalent-reversibly binding warheads remains largely unattended. We previously reported α-ketoamides to be a promising reversible lead motif, yet the cytotoxic activity required further optimization. This work focuses on the lead optimization of phenoxy-substituted α-ketoamides combining the structure-activity relationships from the primed and the non-primed site of the proteasome β5 subunit. Our optimization strategy is accompanied by molecular modeling, suggesting occupation of P1′ by a 3-phenoxy group to increase β5 inhibition and cytotoxic activity in leukemia cell lines. Key compounds were further profiled for time-dependent inhibition of cellular substrate conversion. Furthermore, the α-ketoamide lead structure 27 does not affect escape response behavior in Danio rerio embryos, in contrast to bortezomib, which suggests increased target specificity.
- Stubba, Daniel,Bensinger, Dennis,Steinbacher, Janika,Proskurjakov, Lilia,Salcedo Gómez, álvaro,Schmidt, Uwe,Roth, Stefan,Schmitz, Katja,Schmidt, Boris
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supporting information
p. 2005 - 2022
(2019/11/22)
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- Catalytic asymmetric intramolecular hydroarylations of ω-aryloxy- and arylamino-tethered α,β-unsaturated aldehydes
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The first enantioselective organocatalytic intramolecular hydroarylations of phenol and aniline-derived enals were investigated. The proposed method provided an atom economic and straightforward approach to optically active chromans and tetrahydroquinolines in high enantioselectivities and in good yields. The study demonstrated the efficiency of organocatalysis to achieve the first asymmetric intramolecular arylation of ω aryloxy- arylamino-tethered α, and β-unsaturated aldehydes using a chiral secondary amine catalyst. Proposed transformation method resulted in the production of functionalized chromans and tetrahydroquinoline in high enantiopurity. The study also examined the scope of substrates in this organocatalytic reaction using a catalyst 4/p-TsOH.H2O in diethyl ether. The catalyst screening observed a higher yield up to 83% and comparable enantiometric excess up to 88% that can be obtained in a chiral secondary amine employed as the reaction catalyst.
- Lu, Hai-Hua,Liu, Hui,Wu, Wei,Wang, Xu-Fan,Lu, Liang-Qiu,Xiao, Wen-Jing
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supporting information; scheme or table
p. 2742 - 2746
(2009/12/03)
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- Cerium(IV) induced oxidative coupling of simple phenols in the presence and absence of hydrogen peroxide: A comparative study of product distribution
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The reaction of cerium(IV) ammonium nitrate with simple phenols (2-, 3- and 4-methylphenols) has been examined in the presence and absence of hydrogen peroxide.It has been observed that though the oxophilicity of cerium(IV) can be controlled by addition of hydrogen peroxide in the reaction medium, there is also a difference in the nature of products formed.The reaction can be used to obtain new terphenyls (3a, 3b and 3e), biphenyls (2a, and 2e), 2-hydroxy-1,9-dimethyl-7-nitro-dibenzyl-p-dioxin (4) and 3,7-dimethyl-1,9-dinitrodibenzofuran (5) in acceptable net yields.
- Chakrabarty, Kakoli,Chawla, H. Mohindra,Suresh, Valiya Veettil
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p. 266 - 274
(2007/10/02)
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- Reaction of cerium(IV) ammonium nitrate with simple phenols in a silica gel matrix
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The oxophilicity of cerium(IV) ammonium nitrate is moderated by the addition of hydrogen peroxide.The reaction with simple phenols becomes regioselective when carried out in a silica gel matrix.The methodology has been employed for the synthesis of new functionalized terphenyls and biphenyls.
- Chakrabarty, K,Chawla, H M,Suresh, V V
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p. 464 - 466
(2007/10/02)
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- Synthesis of Nitrobis- and Nitrotris-cresols Using Cerium (IV) Ammonium Nitrate
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Cerium (IV) ammonium nitrate (CAN) has been conveniently employed for the first time to obtain nitro substituted bis- and tris-cresols which are otherwise obtained via lengthy and difficult routes.This is the first report on one-pot and one-step synthesis of oxidatively coupled cresols.Plausible mechanism for the reaction involved has also been suggested.
- Chaudhuri, Kakoli,Chawla, H. Mohindra
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p. 272 - 273
(2007/10/02)
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