244-63-3Relevant articles and documents
Determination of tryptophane in plasma with a spectrofluorometer system.
Steinhart,Sandmann
, p. 950 - 952 (1977)
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N2,N9-Bis(Substituted benzyl)-β-Carbolineum Bromides as Potential Anticancer Therapeutics: Design, Synthesis, Cytotoxicity, Drug-DNA Intercalation and In-Silico Binding Properties
Hamali, Muhamad Azwan,Kamaruzaman, Nur Azzalia,Mansor, Sharif Mahsufi,Mohideen, Mazlin,Mordi, Mohd Nizam,Rahman, A. F. M. Motiur
, (2021)
The present study reports a series of novel N2,N9-bis(substituted benzyl)-β-carbolineum bromides (4a-f) synthesized from L-tryptophan in three steps with excellent yields (>80%). The structures of synthesized compounds 4a-f were confirmed by 1H- and 13C-NMR, FT-IR, LC-MS (ESI-MS) spectrum and elemental analysis. Meanwhile, the crystal structure for compound 4f was determined by X-ray single-crystal diffraction. The crystal belongs in monoclinic space group in P121/c1 space group with a = 13.253(6) ?, b = 20.809(10) ?, c = 9.116(6) ?, β = 107.215(13)°, V = 2401.4(19) ?3 and Z = 4, F(000) = 1048, Dc = 1.403 Mg/m3 and μ = 1.743 mm?1. Compounds 4a-f were evaluated for their in-vitro anticancer activity against selected human cancer cell lines, such as HT-29 (colorectal adenocarcinoma), HeLa (cervical carcinoma), HepG2 (hepatocellular carcinoma) and K562 (chronic myelogenous leukaemia, CML). Results showed that compounds 4a-f exerted excellent cytotoxicity effect with IC50 values ranging from 0.36-1.08 μM against K562 human CML cell line. It was found that synthesized β-carbolines are much less toxic towards non-cancer cell lines BALB/c3T3 and Hs-27, in comparison to cisplatin and doxorubicin, which were employed as positive controls. To investigate the binding mode of these compounds against DNA, spectroscopic studies were conducted. Subsequent UV-Visible and in-silico (molecular docking) studies revealed that compound 4f interacts with DNA through intercalation. Based on the present findings, it was suggested that compound 4f has a great potential to be developed as a novel anticancer agent.
Preparation and a novel rearrangement reaction of 1,2,3,4-tetrahydro-9- hydroxy-β-carboline, and their applications for the total synthesis of (±)- coerulescine
Somei,Noguchi,Yamagami,Kawada,Yamada,Yamada
, p. 7 - 10 (2000)
Novel 9-hydroxy-β-carboline derivatives were produced for the first time. A novel rearrangement reaction of 1,2,3,4-tetrahydro-9-hydroxy-β- carbolines was discovered to give 3,3-disubstituted oxindoles, which was successfully applied to the total synthesis of (±)-coerulescine.
Synthesis method of 9H-pyrido [3, 4-b] indole
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Paragraph 0027-0050, (2021/11/03)
The invention discloses a synthesis method of 9H-pyrido [3, 4-b] indole. The method comprises the following steps: taking tryptophan and chloroform as basic reaction raw materials, taking ferric salt as a catalyst, then adding alkali, carrying out cyclization aromatization reaction through free radical series connection, and finally carrying out post-treatment to obtain the 9H-pyrido [3, 4-b] indole product. According to the method, only commercially available tryptophan is used as a substrate, chloroform is used as a C1 source, a reaction precursor does not need to be prepared in advance, [5 + 1] cyclization aromatization is realized in a free radical series connection mode; and after C-C bond and C-N bond construction as well as decarboxylic acid and dehydrogenation aromatization process, without prior modification, addition of oxidizer, pre-preparation and separation of tetrahydrocarboline compounds, direct construction of pyridine heterocyclic slices can be realized througha one-pot method.
Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles
Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.
, p. 5990 - 6007 (2021/08/24)
Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.
