An overview on synthetic entries to tetrahydro-β-carbolines

Maity, Pradipta; Adhikari, Debasis Das; Jana, Amit Kumar

doi:10.1016/j.tet.2019.01.004

Cited by 72 publications

(49 citation statements)

References 606 publications

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“…THBCs have been reported as anti‐cancer agents [21] and are targeted as mitotic kinase Eg5 and phosphodiesterase‐5. These derivatives were also shown to possess potent anti‐HIV activity, [36] PDE5‐inhibitory activity, [37] and as free radical scavengers [38] . Figure 5 represents some of the β‐carboline derivatives, which are of clinical importance.…”

Section: Chemistry and Diversity Of Carbolinesmentioning

confidence: 99%

“…These derivatives were also shown to possess potent anti-HIV activity, [36] PDE5-inhibitory activity, [37] and as free radical scavengers. [38] Figure 5 represents some of the β-carboline derivatives, which are of clinical importance. The Bischler-Napieralski, [39] Pictet-Spengler, [40] and Graebe-Ullmann [41] reactions are some of the conventional approaches for the Synthesis of β-carboline derivatives.…”

Section: Tetrahydro β-Carboline and Its Derivatives (Thbc)mentioning

confidence: 99%

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Anti‐Tubercular Insights of Carbolines – A Decade Critique

et al. 2021

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Tuberculosis is one of the top 10 leading causes of death worldwide and is caused by the bacteria “Mycobacterium tuberculosis.” The medications used to treat tuberculosis have many deficiencies, including long‐term treatment, expensive medications, etc. The continuing emergence of multidrug resistance (MTR) remains a critical health issue that needs to be tackled urgently. Increased HIV/AIDS co‐infection with tuberculosis has also worsened the condition. Carbolines, nitrogen‐containing tricyclic Compounds have a significant role in medicinal chemistry because of their broad pharmacological properties, such as anti‐tubercular, anti‐bacterial, anti‐leishmanial, anti‐cancer, anti‐viral, etc. A brief description of the anti‐tubercular ability of a diverse set of carbolines collected from the past ten years focused on synthetic procedures, structural‐activity relationship studies, and their molecular mechanism of action was clearly described in the current review.

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Section: Chemistry and Diversity Of Carbolinesmentioning

confidence: 99%

Section: Tetrahydro β-Carboline and Its Derivatives (Thbc)mentioning

confidence: 99%

Anti‐Tubercular Insights of Carbolines – A Decade Critique

et al. 2021

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“…Numerous representatives of this family show various biological activities [ 3 , 4 , 5 ]. The fascinating diversity of structures and medicinal potential [ 6 ] inherent in them encourage several researchers to deal with the synthesis of β-carboline containing natural products and their synthetic derivatives [ 2 , 4 , 7 , 8 , 9 ]. Several commercial drugs or drug candidates such as vinpocetine, brovincamine, abecarnil, cipargamin, tadalafil, reserpine and lurbinectedin contain this unique framework ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of β-Carboline Alkaloids

2021

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β-Carboline alkaloids are a remarkable family of natural and synthetic indole-containing heterocyclic compounds and they are widely distributed in nature. Recently, these alkaloids have been in the focus of interest, thanks to their diverse biological activities. Their pharmacological activity makes them desirable as sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic or antimicrobial drug candidates. The growing potential inherent in them encourages many researchers to address the challenges of the synthesis of natural products containing complex β-carboline frameworks. In this review, we describe the recent developments in the synthesis of β-carboline alkaloids and closely related derivatives through selected examples from the last 5 years. The focus is on the key steps with improved procedures and synthetic approaches. Furthermore the pharmacological potential of the alkaloids is also highlighted.

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“…In particular, the β-carboline based moiety represents the core structure of several pharmaceutical activities [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ], such as anticancer [ 3 , 4 , 13 ], antimicrobial [ 5 ], antimalarial [ 7 ], antiviral [ 9 ], and antifungal activities [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. Many bioactive β-carboline-based compounds have been found to be important sources of drugs and drug leads, and most of them have been isolated from marine invertebrates, such as the marine sponge [ 5 , 6 , 7 , 8 , 10 , 21 , 22 , 23 ], tunicate [ 4 , 24 , 25 ], gorgonian [ 26 ] and alga [ 27 ]. For example, as shown in Figure 1 , Eudistomins and their analogs were isolated from several species of marine organisms, mainly the active Caribbean colonial tunicate, and possessed a wide range of biological activities [ 28 , 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of Plant Pathogenic Fungi

2021

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A series of tetrahydro-ß-carbolines substituted with an alkyl or acyl side chain was synthesized and screened for its antifungal activity against plant pathogenic fungi (Bipolaris oryzae, Curvularia lunata, Fusarium semitectum, and Fusarium fujikuroi). The structure activity relationship revealed that the substituent at the piperidine nitrogen plays an important role for increasing antifungal activities. In this series, 2-octyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (3g) displayed potent antifungal activities with a minimum inhibitory concentration of 0.1 μg/mL, including good inhibitory activity to the radial growth of fungus at a concentration of 100 μg/mL compared to amphotericin B.

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An overview on synthetic entries to tetrahydro-β-carbolines

Cited by 72 publications

References 606 publications

Anti‐Tubercular Insights of Carbolines – A Decade Critique

Anti‐Tubercular Insights of Carbolines – A Decade Critique

Recent Advances in the Synthesis of β-Carboline Alkaloids

Synthesis and Investigation of Tetrahydro-β-carboline Derivatives as Inhibitors of Plant Pathogenic Fungi

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