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Search for "β-carboline" in Full Text gives 23 result(s) in Beilstein Journal of Organic Chemistry.
Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products
Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92
- Nisha Devi Virender Singh Department of Chemistry, DAV University, Jalandhar-Pathankot National Highway (NH 44), Jalandhar, 144012, Punjab, India Department of Chemistry, Central University of Punjab, Bathinda, India 10.3762/bjoc.18.92 Abstract β-Carboline is a privileged class of the alkaloid
- family and is associated with a broad spectrum of biological properties. 3-Formyl-9H-pyrido[3,4-b]indole is a such potent precursor belonging to this family which can be tailored for installing diversity at various positions of β-carboline to generate unique molecular hybrids of biological importance
- . The present work is a step towards this and assimilates the results related to the exploration of 3-formyl-9H-β-carbolines for the synthesis of β-carboline C-3 substituted MBH adducts followed by evaluation of their fluorescent characteristic. The effect of contact time, solvent system, concentration
On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets
Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126
Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation
Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101
- -pyrido[3,4-b]indole (β-carboline) is the most naturally abundant, present for instance, in the alkaloid harmine, a well-known selective inhibitor of monoamine oxidase-A (MAO-A) [1]. On the contrary, 5H-pyrido[4,3-b]indoles (γ-carbolines) are comparatively less examined, although these heterocycles have
- traces of any β-carboline product were observed, which proves that the heterocyclization reaction is highly regiospecific. Optical properties of γ-carbolines Interestingly, the γ-carboline derivatives were found to be highly fluorescent under UV light irradiation. A systematic literature survey revealed
N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles
Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86
Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
Beilstein J. Org. Chem. 2021, 17, 730–736, doi:10.3762/bjoc.17.62
- structures of the compounds were elucidated through 1D and 2D NMR spectroscopy. It was determined that trigonoine A was a β-carboline alkaloid containing a 2,8-diazabicyclo[3.3.1]nonane ring system, while trigonoine B (1) was formed by a combination of 2,3-dihydroquinolin-4-one and 3H-pyrrolo[2,3-c]quinoline
- rearranged from a β-carboline skeleton (Figure 1). Additionally, the antihepatitis B virus (HBV) activity of the alkaloids was evaluated in vitro using an HBV-transfected HepG2 cell line. The antihuman immunodeficiency virus (HIV) properties were also investigated to determine whether trigonoine A and B
A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach
Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20
- ]. Similarly, Maurya developed a microfluidic photoreactor for the synthesis of a fused β-carboline from an α-ketovinyl azide and a 1,2,3,4-tetrahydro-β-carboline (Scheme 1b) [30]. More recently, Kappe reported the generation of 2H-azirines under continuous flow conditions, and their transformation into
Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction
Beilstein J. Org. Chem. 2020, 16, 2073–2079, doi:10.3762/bjoc.16.174
- octahydroindole [10], tetrahydroquinoline [11], tetrahydroisoquinoline [11][12], β-carboline [13], morpholine [14], and isoindoline [15] moieties have been developed. Obtained in an enantiomerically pure form, phosphonoproline and its analogues [16][17][18][19] were among the first compounds in this series
Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146
- -metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et3N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an
- incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed
- excellent light-emitting properties with quantum yields (ΦF) up to 47%. Keywords: benzothiophene; β-carboline; metal-free; photophysical properties; sulfur insertion; Introduction The pyrido[3,4-b]indole moiety, commonly referred as β-carboline, is the core unit of about one quarter of all natural
Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules
Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68
- reaction for accessing bioactive organic molecules is found in the complex synthesis of manzamine alkaloids. These efficient antitumor agents, originally isolated from several genera of marine sponges, contain a pentacyclic core with a pendant β-carboline moiety. Their total synthesis implies an elaborate
Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica
Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293
- were found to produce the same compound. So far, pigmentosin A (1) was reported only from lichenized fungi [20][21], and thus this is the first report of this compound stemming from another group of fungi. Recently, we have reported on the two new β-carboline alkaloid derivatives gibellamines A and B
Mannich base-connected syntheses mediated by ortho-quinone methides
Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43
- , the synthesis of 2,3,4,9-tetrahydro-1H-xantene-1-ones (20) has been published by the same research group. The synthetic protocol was then extended to isolate benzo[a]xanthen-11-ones or chromeno[3,2-g]β-carboline-8,13-dione starting from 2-naphthol and 1H-β-carboline-1-one Mannich bases [71]. Although
- of Evodia rutaecarpa alkaloids, starting from 6-methoxy-4,9-dihydro-β-carboline and various substituted 1-aminoalkyl-2-naphthols [84] (Scheme 5). Reactions with electron rich aromatic compounds The formation of aza-o-QMs is also possible, if the initial phenolic Mannich base bears an aromatic moiety
Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds
Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162
- carbon in oxidative dehydrogenation was also well explored in the last few decades. In most of these reactions, either an additive or an acceptor is used along with palladium to improve the rate of the reaction. Recently Török et al. [95] reported the synthesis of 1-aryl-β-carboline using montmorillonite
- K-10 and Pd/C as catalysts. The microwave-assisted synthesis of β-carboline 96 from tetrahydro-β-carboline 95 using catalytic Pd/C and lithium carbonate at high temperature is also reported [96]. This high yielding procedure gets completed within a few minutes (Scheme 36). Although the reaction
- oxidative dehydrogenation in the synthesis of β-carboline natural products norharmine (111), harmane (112) and eudistomin U (113) [101]. The general synthetic scheme involved the synthesis of the respective tetrahydro-β-carboline precursors of the said natural products by Pictet–Spengler reaction of
Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines
Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46
- , recently, we have reported the activation of an imide carbonyl group with TfOH, for the synthesis of tetrahydroisoquinoline (THIQ) and tetrahydro-β-carboline (THBC) skeletons and related alkaloids [22][23][24][25][26]. The present study, describes the synthesis of 4-benzenesulfonylpiperazine-2,6-dione
(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers
Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48
- electron-rich diene, which reacts with substituted dihydroisoquinoline 14 and dihydro-β-carboline 15, so that cyclohexanone derivatives 16 and 17 will be produced, respectively (Scheme 8) [19]. Also, a cyclic derivative of 13 was utilized (not shown). This aza-Diels–Alder reaction provides products with
Synthesis of constrained analogues of tryptophan
Beilstein J. Org. Chem. 2015, 11, 1997–2006, doi:10.3762/bjoc.11.216
- analogues received less attention with respect to others congeners. Constraints and modifications in the tryptophan core have been mainly attained following two different strategies: embodying the nitrogen atom of the amino acid function in a β-carboline framework or inserting a linking group between the α
- -1,2,3,4-tetrahydrocarbazole-3-carboxylic acid as a rigid analogue of α-methyltryptophan, a well known unnatural amino acid able to inhibit α-chymotrypsin activity, Figure 2 (A). Hardening tryptophan in β-carboline or carbazole frameworks has been used by Hénichart and co-workers in their studies devoted
- hormone (GnRH) [13][14], Figure 2 (C). Finally, in the field of therapeutic peptides, constrained tryptophan residues of the β-carboline family (L-Tpi and D-Tpi), were used by Grieco and co-workers in the study and development of urotensin-II receptor (UTR) peptide ligands [15], Figure 2 (D). Switching
Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
Beilstein J. Org. Chem. 2014, 10, 848–857, doi:10.3762/bjoc.10.81
- ] and anticancer [5] activities. The bioactive β-carboline alkaloids canthinone [6] and vinpocitine [7] also bear these substructures. Vinpocetine is a dehydrated derivative of the natural alkaloid of vincamine [8]. It is reported to have cerebral blood-flow enhancing [7] and neuroprotective effects [9
Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics
Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50
An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y
Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45
- – 500085, India 10.3762/bjoc.10.45 Abstract A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of
- dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids. Keywords: Bischler–Napieralski reaction; dihydro-β-carboline derivatives; dihydro
- -eudistomin; eudistomin; keto amide; oxidative amidation; Introduction β-Carboline alkaloids [1] are widespread in plants, animals and some are formed naturally in the biological system. Rinehart et al. [2] reported the isolation of β-carboline alkaloids such as eudistomins [3] and several of its analogues
Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction
Beilstein J. Org. Chem. 2013, 9, 1235–1242, doi:10.3762/bjoc.9.140
- provided broad substrate scope and diversity. This is indeed the first report of the use of TCT as a catalyst for the Pictet–Spengler reaction. Keywords: β-carboline; cyanuric chloride; 6-endo cyclization; Pictet–Spengler; TCT; Introduction The Pictet–Spengler reaction is an important class of name
- reaction employed extensively for the synthesis of tetrahydro-β-carboline [1][2][3][4][5][6][7][8][9]. Typically, the Pictet–Spengler reaction is a two-step reaction. The first step is the condensation of aliphatic amine substrates such as tryptophan/tryptamine and aldehydes to generate the intermediate
- imine in situ. The intermediate imine then undergoes a 6-endo cyclization to furnish the cyclized product, tetrahydro-β-carboline [10]. Recently, arylamines have been employed instead of the aliphatic amines for the Pictet–Spengler reaction. These reactions are generally termed as modified Pictet
The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure
Beilstein J. Org. Chem. 2013, 9, 147–154, doi:10.3762/bjoc.9.17
- , piazza Leonardo da Vinci 32, 20132 Milano, Italy 10.3762/bjoc.9.17 Abstract Aiming at restricting the conformational freedom of tryptophan-containing peptide ligands, we designed a THBC (tetrahydro-β-carboline)-DKP (diketopiperazine)-based peptidomimetic scaffold capable of arranging in an unusual α
- -carboline; Introduction From a long time, the alkaloids containing the 1,2,3,4-tetrahydro-β-carboline (THBC) skeleton have represented important lead structures in view of their wide range of biological activities [1], mainly due to their interaction with the central nervous system [2][3][4][5][6][7
- synthesis of peptidomimetic 1a (Scheme 1). Starting from L-tryptophan methyl ester and N-Cbz-aminoacetaldehyde dimethyl acetal [43], tetrahydro-β-carboline 2 was obtained in good yield and high diastereoselectivity (dr 70% from 1H NMR) by means of Pictet–Spengler reaction [44] and subsequent chromatographic
Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
Beilstein J. Org. Chem. 2012, 8, 1901–1908, doi:10.3762/bjoc.8.220
- developed for the construction of a functionalized natural product, meridianin, and its post conversion to pyrimido-β-carboline by cationic π- cyclization. The strategy involves the introduction of an amino group at the C-5 of the pyrimidine ring and utilizing the nucleophilictiy of the C-2 in the indole
- -based alkaloid meridianins into annulated indole-based polyheterocycles as novel chemprobes. For the synthesis of meridianin-inspired indole-based annulated polyheterocycles, we proposed to transform tethered biheterocycles into β-carboline-based polyheterocycles, a new prototype hitherto not reported
- inhibition [48] to inhibition of cGMP-dependent processes [49][50]. In this communication, we report engineering of naturally occurring tethered indole-based biheterocyclic alkaloid meridianins into β-carboline-derived tetracyclic polyheterocycles by amino functionalization of the pyrimidine ring followed by
Synthesis and in silico screening of a library of β-carboline-containing compounds
Beilstein J. Org. Chem. 2012, 8, 1048–1058, doi:10.3762/bjoc.8.117
- , School of Pharmacy; Drug Discovery Institute; Department of Computational Biology; University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA 10.3762/bjoc.8.117 Abstract The synthesis of a library of tetrahydro-β-carboline-containing compounds in milligram quantities is described. Among the unique
- them are in accordance with Lipinski’s rules. Virtual docking and ligand-based target evaluations were performed for the β-carboline library compounds and selected synthetic intermediates to assess the therapeutic potential of these small organic molecules. These compounds have been deposited into the
- NIH Molecular Repository (MLSMR) and may target proteins such as histone deacetylase 4, endothelial nitric oxide synthase, 5-hydroxytryptamine receptor 6 and mitogen-activated protein kinase 1. These in silico screening results aim to add value to the β-carboline library of compounds for those
Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine
Beilstein J. Org. Chem. 2011, 7, 1407–1411, doi:10.3762/bjoc.7.164
- important class of naturally occurring compounds containing the β-carboline motif found in a number of biologically active molecules, and which have recently been shown to be active against Alzheimer’s disease [1][2], bacterial infection [3], inflammation [4][5], HIV and AIDS [6] and various forms of
- cancers [7][8][9][10][11][12]. The wide range of therapeutic applications of these molecules highlights the importance of carbolines as a synthetic target in medicinal chemistry. The formation of the β-carboline ring system in nature is well understood and biosynthetically has been shown to proceed by
- means of either a Pictet–Spengler or a Bischler–Napieralski cyclization followed by an oxidative dehydrogenation process [13][14][15]. Inspired by nature’s example, we wished to design a synthetic route to the β-carboline scaffold, which was biomimetic and could be carried out in a single operation. One
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