Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents

Cao, Rihui; Guan, Xiangdong; Shi, Buxi; Chen, Zhiyong; Ren, Zhenhua; Peng, Wenlie; Song, Huacan

doi:10.1016/j.ejmech.2010.02.036

Cited by 56 publications

(29 citation statements)

References 42 publications

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“…In vitro cytotoxic activities of thesed erivatives were investigated against ag roup of human tumor cell lines and their results indicatedt hat electropositive atoms at the C3 positionw ere unfavorable for antitumor activity. [58] A similar synthesis of compounds 154 was also reported by Lu and co-workers. [59] Abranyi-Balogh et al also describedasimilarf our-step synthesis of b-carboline-3-carbaldehydes (158)s tartingf rom racemic tryptophan methyl ester through aP ictet-Spengler cyclization reactionw ith aromatic carbaldehydes under acidic conditions, followed by 2-iodoxybenzoic acid (IBX)-mediated dehydrogenation of tetrahydro-b-carbolines (155)a nd subsequent reduction of the ester moiety in compound 156 with NaBH 4 to afford an alcohol (157).…”

Section: Synthesis and Application Of 3-formyl-9h-b-carbolinessupporting

confidence: 65%

“…[40] This reaction was accompanied by the formation of monomeric b-carboline derivatives that contained ad iamine chain (56 and 58). Furthermore, monomeric as well as dimeric b-carboline derivatives (55)(56)(57)(58) were screenedf or their anticancer and antimalarial properties and the biological assay revealed that bis-b-carboline derivatives were more potent than the corresponding monomeric derivatives against both cancer and malarialcell lines.…”

Section: Synthesis Of C1-tethered B-carboline Frameworkmentioning

confidence: 99%

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1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

et al. 2017

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b-Carboline, ap rivileged scaffold in the alkaloid family,h as ab road spectrum of medicinal properties and is found in severalc ommercial drugs, such as tadalafil, cipargamin, anda becarnil. Owing to the immense pharmacological importance of b-carboline derivatives, their synthesis has been one of the frontier areas of research in recent years. In this context,1 (3)-formyl-9H-b-carbolines are promising "aldo-X" bifunctional building blocks (AXB3s) that offer alternate avenues for the diversity-oriented synthesis of b-carboline derivatives. This Focus Review is an assimilation of recent literature (2011)(2012)(2013)(2014)(2015)(2016)(2017) pertaining to the synthesis and applicationso f1 (3)-formyl-b-carbolines for the construction of b-carboline-tethered and -fused moleculara rchitectures. In addition, the medicinal potential of b-carboline derivatives has been highlighted.

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Section: Synthesis and Application Of 3-formyl-9h-b-carbolinessupporting

confidence: 65%

Section: Synthesis Of C1-tethered B-carboline Frameworkmentioning

confidence: 99%

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

et al. 2017

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“…The dataset was adopted from the work of Cao et al [55] in which they reported the cytotoxic potential of a number of synthesized -carbolines against a panel of human tumor cell lines ( Table 1). The 3D structures of dataset were constructed in SYBYL7.3 molecular modeling package (Tripos Inc., St. Louis, USA), and the energy minimizations were performed using Tripos force field with a distancedependent dielectric and the Powell conjugate gradient algorithm convergence criterion of 0.01 kcal/molÅ.…”

Section: Datasetmentioning

confidence: 99%

3D-QSAR and Docking Studies of a Series ofβ-Carboline Derivatives as Antitumor Agents of PLK1

Ghasemi

Davoudian

2014

Journal of Chemistry

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An alignment-free, three dimensional quantitative structure-activity relationship (3D-QSAR) analysis has been performed on a series ofβ-carboline derivatives as potent antitumor agents toward HepG2 human tumor cell lines. A highly descriptive and predictive 3D-QSAR model was obtained through the calculation of alignment-independent descriptors (GRIND descriptors) using ALMOND software. For a training set of 30 compounds, PLS analyses result in a three-component model which displays a squared correlation coefficient (r2) of 0.957 and a standard deviation of the error of calculation (SDEC) of 0.116. Validation of this model was performed using leave-one-out,q2looof 0.85, and leave-multiple-out. This model gives a remarkably highr2pred(0.66) for a test set of 10 compounds. Docking studies were performed to investigate the mode of interaction betweenβ-carboline derivatives and the active site of the most probable anticancer receptor, polo-like kinase protein.

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“…Thus, the methoxy-substituent at position-7 of beta-carboline might contribute to the significant neurotoxic side effect. On the other hand, the prolonged substituents at position-7 eliminated neurotoxic effects completely [ 9 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

Novel harmine derivatives for tumor targeted therapy

Wang

et al. 2015

Oncotarget

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Harmine is a beta-carboline alkaloid found in medicinal plant PeganumHarmala, which has served as a folk anticancer medicine. However, clinical applications of harmine were limited by its low pharmacological effects and noticeable neurotoxicity. In this study, we modified harmine to increase the therapeutic efficacy and to decrease the systemic toxicity. Specifically, two tumor targeting harmine derivatives 2DG-Har-01 and MET-Har-02 were synthesized by modifying substituent in position-2, -7 and -9 of harmine ring with two different targeting group2-amino-2-deoxy-D-glucose (2DG) and Methionine (Met), respectively. Their therapeutic efficacy and toxicity were investigated both in vitro and in vivo. Results suggested that the two newharmine derivatives displayed much higher therapeutic effects than non-modified harmine. In particular, MET-Har-02 was more potent than 2DG-Har-01 with promising potential for targeted cancer therapy.

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Design, synthesis and 3D-QSAR of β-carboline derivatives as potent antitumor agents

Cited by 56 publications

References 42 publications

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

3D-QSAR and Docking Studies of a Series ofβ-Carboline Derivatives as Antitumor Agents of PLK1

Novel harmine derivatives for tumor targeted therapy

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