- Selectivity-tunable oxidation of tetrahydro-β-carboline over an OMS-2 composite catalyst: preparation and catalytic performance
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Controlling the reaction selectivity of organic transformations without losing high conversion is always a challenge in catalytic processes. In this work, a H3PO4·12WO3/OMS-2 nanocomposite catalyst ([PW]-OMS-2) was prepared through the oxidation of a Mn(ii) salt with sodium phosphotungstate by KMnO4. Comprehensive characterization indicates that different Mn2+precursors significantly affected the crystalline phase and morphology of the as-synthesized catalysts and only MnSO4·H2O as the precursor could lead to a cryptomelane phase. Moreover, [PW]-OMS-2 demonstrated excellent catalytic activity toward aerobic oxidative dehydrogenation of tetrahydro-β-carbolines due to mixed crystalline phases, enhanced surface areas, rich surface oxygen vacancies and labile lattice oxygen species. In particular, β-carbolines and 3,4-dihydro-β-carbolines could be obtained from tetrahydro-β-carbolines with very high selectivity (up to 99%) over [PW]-OMS-2viatuning the reaction solvent and temperature. Under the present catalytic system, scalable synthesis of a β-carboline was achieved and the composite catalyst showed good stability and recyclability. This work not only clarified the structure-activity relationship of the catalyst, but also provided a practical pathway to achieve flexible, controllable synthesis of functional N-heterocycles.
- Bi, Xiuru,Tao, Luyao,Yao, Nan,Gou, Mingxia,Chen, Gexin,Meng, Xu,Zhao, Peiqing
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supporting information
p. 3682 - 3692
(2021/03/22)
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- Asymmetric Biocatalytic Synthesis of 1-Aryltetrahydro-β-carbolines Enabled by “Substrate Walking”
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Stereoselective catalysts for the Pictet–Spengler reaction of tryptamines and aldehydes may allow a simple and fast approach to chiral 1-substituted tetrahydro-β-carbolines. Although biocatalysts have previously been employed for the Pictet–Spengler react
- Eger, Elisabeth,Iding, Hans,Kroutil, Wolfgang,Kuhn, Bernd,Schrittwieser, Joerg H.,Wetzl, Dennis
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p. 16281 - 16285
(2020/11/30)
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- Metal free one pot synthesis of Β-carbolines via a domino Pictet-Spengler reaction and aromatization
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A convenient and efficient metal free, atom economical flexible synthesis of β-carbolines involving a domino Pictet-Spengler reaction and aromatization in oxygen atmosphere in N-methyl-2-pyrollidone (NMP) is described. Variety of aryl, heteroaryl and aliphatic aldehydes were found to be good substrates for this methodology. Several β-carbolines (6a-6t) and β-carboline methyl esters (7a-7e) were synthesized using this methodology.The same reaction carried out in argon atmosphere in the presence of catalytic amount of acid in NMP furnished, tetrahydro-β-carbolines (4a-4g).
- Ramu,Srinath,kumar, A. Aswin,Baskar,Ilango,Balasubramanian
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- Tetrahydro Beta-carboline derivative as well as preparation method and application of derivative
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The invention discloses a tetrahydro Beta-carboline derivative shown in a formula I as described in the specification, which is a novel compound with histone deacetylase inhibiting activity and can beused for treating some diseases with abnormally high expression of histone deacetylase effectively. The histone deacetylase is closely related to occurrence and development of cancers. The serial compounds can inhibit proliferation of tumor cells effectively by inhibiting the activity of the histone deacetylase and inducing differentiation and apoptosis of the tumor cells, so as to achieve the purpose of treating cancers.
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Paragraph 0060; 0137
(2018/04/26)
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- Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of the Breast Cancer Resistance Protein (ABCG2)
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The breast cancer resistance protein (ABCG2) transports chemotherapeutic drugs out of cells, which makes it a major player in mediating multidrug resistance (MDR) of cancer cells. To overcome this mechanism, inhibitors of ABCG2 can be used. Only a few potent and selective ABCG2 inhibitors have been discovered, i.e., fumitremorgin C (FTC), Ko143, and the alkaloid harmine, which contain a tetrahydro-β-carboline or β-carboline backbone, respectively. However, toxicity and or instability prevent their use in vivo. Therefore, there is a need for further potent inhibitors. We synthesized and pharmacologically investigated 37 tetrahydro-β-carboline derivatives. The inhibitory activity of two compounds (51, 52) is comparable to that of Ko143, and they are selective for ABCG2 over ABCB1. Furthermore, they are able to reverse the ABCG2-mediated resistance toward SN-38 and inhibit the ATPase activity. The cytotoxicity data show that their inhibitory effect is substantially higher than their toxicity.
- Spindler, Anna,Stefan, Katja,Wiese, Michael
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p. 6121 - 6135
(2016/07/26)
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- Iodine-catalyzed highly effective pictet-spengler condensation: An efficient synthesis of tetrahydro-β-carbolines
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Molecular iodine was found to be an efficient catalyst for the two-component Pictet-Spengler condensation of tryptamine with aldehydes, which leads to the formation of tetrahydro-β-carbolines in high yields. Copyright Taylor & Francis Group, LLC.
- Prajapati, Dipak,Gohain, Mukut
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experimental part
p. 4426 - 4433
(2009/04/06)
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- Reaction of 1-substituted tetrahydro-β-carbolines with activated alkynes - A new original approach to the synthesis of tetrahydroazocino[5,4-b] indoles
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The transformations of 1-substituted tetrahydro-β-carbolines by the action of activated alkynes were studied. The action of dimethyl acetylenedicarboxylate in methanol gives products of the opening of the tetrahydropyridine fragment, namely, 2-methoxyalkylindoles. The action of ethyl propiolate in ethanol and of tosylacetylene in methanol gives mixtures of azocino[5,4-b]indoles and 2-alkoxyindoles. The action of ethyl propiolate in acetonitrile gives azocinoindoles.
- Voskressensky,Borisova,Kulikova,Dolgova,Kleimenov,Sorokina,Titov,Varlamov
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p. 587 - 598
(2008/12/21)
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- Antibacterial compounds
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Compounds of the formula (I) are disclosed and are useful in the treatment bacterial infections: wherein: R1 is Ar or Het; R2 is C1-6alkyl, (R″)2N-(CH2)m— or Ar—C0-6alkyl; X is H
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- Microwave assisted Pictet-Spengler and Bischler-Napieralski reactions
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Pictet-Spengler and Bischler-Napieralski reaction products have been prepared-using microwave irradiation on silicagel support under solvent free condition. Microwave assisted reactions have resulted in better yields of the desired products than prepared
- Pal, Bikash,Jaisankar, Parasuraman,Giri, Venkatachalam S.
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p. 2339 - 2348
(2007/10/03)
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- Synthesis of 2-acyltetrahydro-β-carbolines by an intramolecular α- amidoalkylation reaction
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2-Acyltetrahydro-β-carbolines 7 have been obtained by cyclization of adducts 5 from imines 3 of tryptamine 1 and aldehydes 2 with acyl chlorides 4 as a result of an intramolecular α-amidoalkylation reaction in the presence of bases as N,N-dimethylaniline or Et3N.
- Venkov, Atanas P.,Boyadjieva, Atanaska K.
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p. 487 - 494
(2007/10/03)
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