A review of the synthesis of α-carbolines

Wadsworth, Andrew D.; Naysmith, Briar J.; Brimble, Margaret A.

doi:10.1016/j.ejmech.2014.11.038

Cited by 58 publications

(33 citation statements)

References 59 publications

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“…Harmine, a β‐carboline, has been identified as an inhibitor of DYRK family of kinases . The α‐carboline (pyrido[2,3‐ b ]indole) structure is present in some natural products that show cytotoxic and anticancer activity, as well as effects on central nervous system . In general, carbolines have a potential for a broad range of biological effects including antitumor, antimalarial, antiproliferative, antifungal, and antibacterial activities .…”

Section: Introductionmentioning

confidence: 99%

“…The previously used routes for the synthesis of pyrido[2,3‐ b ] indole derivatives are based on the annulation of azaindoles, Diels−Alder reaction, annulation of indoles, Vilsmeier−Haack reaction, palladium‐catalyzed reactions of 2‐amidinylindole‐3‐carbaldehyde with acetophenones, and 6π‐electrocyclization of indole‐3‐alkenyl oximes . Some of these methods require multistep routes of synthesis, long reaction time, and costly substrates.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Pyrido[2,3‐b]indole Derivatives Using Silicates of Group 1 and 2 Metals

Sheikh

Fazlinia

2018

Journal of Heterocyclic Chem

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An efficient synthesis of 2,4‐diaryl‐9H‐pyrido[2,3‐b] indole derivatives in aqueous medium via the three‐component reaction of indolin‐2‐one, a chalcone and ammonium acetate was developed using Na2SiO3, K2SiO3, Li2SiO3, CaSiO3, MgSiO3, BaSiO3, SrSiO3, and ZnSiO3 as catalysts. Results of activity evaluations indicated that among of the metal silicate used alkali metal silicates exhibits much higher activity than other samples due to the stronger basicity power and higher solubility in water. Under the optimum reaction conditions, all of the reactions with diverse aromatic aldehydes provided high yields in low reaction times.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of Pyrido[2,3‐b]indole Derivatives Using Silicates of Group 1 and 2 Metals

Sheikh

Fazlinia

2018

Journal of Heterocyclic Chem

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“…Whereas b-and g-derivatives are widely spread in nature [1] a-carbolines are comparable uncommon. [5] These molecules apply in the medical sector as agents either for the treatment of cancer [3] and chronic inflammatory diseases (e. g. rheumatoid arthritis) [2], [4] or against Alzheimer's and Parkinson's disease. [5] These molecules apply in the medical sector as agents either for the treatment of cancer [3] and chronic inflammatory diseases (e. g. rheumatoid arthritis) [2], [4] or against Alzheimer's and Parkinson's disease.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of 5,7‐disubstituted 5,7‐dihydropyrido[2,3‐b:6,5‐b′]diindoles

et al. 2017

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A new and efficient two-step procedure for the preparation of 5,7-disubstituted 5,7-dihydropyrido[2,3-b:6,5-b']diindoles, containing aryl-, benzyl-as well as alkyl-substituents has been developed. This methodology consists of a chemoselective double Suzuki-Miyaura cross-coupling reaction followed by a fourfold Buchwald-Hartwig amination reaction. UV/VIS absorption and fluorescence measurements have been carried out for a selected series of compounds. The results are summarized and compared with those of the isomeric 5,7-disubstituted 5-7-dihydropyrido[3,2b:5,6-b']diindoles.

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“…Carbolines have a tricyclic pyridoindole structure and are classified as α-, β-, γ-, or δ-carbolines, depending on the position of the pyridine nitrogen relative to the indole. The naturally occurring compounds show a range of biological activities, prompting the synthesis and study of related derivatives [15–17]. In comparison with the well-known β-carbolines, an α-carboline (1-azacarbazole) skeleton is rarely present in alkaloids found in nature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structure-activity relationship studies of novel 3,9-substituted α-carboline derivatives with high cytotoxic activity against colorectal cancer cells

Lin

Chen

Tseng

et al. 2016

European Journal of Medicinal Chemistry

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In our continued focus on 1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole (YC-1) analogs, we synthesized a novel series of 3,9-substituted α-carboline derivatives and evaluated the new compounds for antiproliferactive effects. Structure activity relationships revealed that a COOCH3 or CH2OH group at position-3 and substituted benzyl group at position-9 of the α-carboline nucleus were crucial for maximal activity. The most active compound, 11, showed high levels of cytotoxicity against HL-60, COLO 205, Hep3B, and H460 cells with IC50 values of 0.3, 0.49, 0.7, and 0.8 μM, respectively. The effect of compound 11 on the cell cycle distribution demonstrated G2/M arrest in COLO 205 cells. Furthermore, mechanistic studies indicated that compound 11 induced apoptosis by activating death receptor and mitochondria dependent apoptotic signaling pathways in COLO 205 cells. The new 3,9-substituted α-carboline derivatives exhibited excellent anti-proliferative activities, and compound 11 can be used as a promising pro-apoptotic agent for future development of new antitumor agents.

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A review of the synthesis of α-carbolines

Cited by 58 publications

References 59 publications

Preparation of Pyrido[2,3‐b]indole Derivatives Using Silicates of Group 1 and 2 Metals

Preparation of Pyrido[2,3‐b]indole Derivatives Using Silicates of Group 1 and 2 Metals

Synthesis and properties of 5,7‐disubstituted 5,7‐dihydropyrido[2,3‐b:6,5‐b′]diindoles

Synthesis and structure-activity relationship studies of novel 3,9-substituted α-carboline derivatives with high cytotoxic activity against colorectal cancer cells

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