A Total Synthesis of 1-Methoxycanthin-6-one: An Efficient One-Pot Synthesis of the Canthin-6-one Skeleton from β-Carboline-1-carbaldehyde

Suzuki, Hideharu; Adachi, Makoto; Ebihara, Yuki; Gyoutoku, Hiroshi; Furuya, Hinako; Murakami, Yasuoki; Okuno, Hiroaki

doi:10.1055/s-2004-834915

Cited by 23 publications

(9 citation statements)

References 9 publications

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“…NMR spectra were obtained on a Bruker Avance 250 spectrometer operating at 250 and 62.9 MHz for 1 H and 13 C NMR spectra, respectively (CAI de Resonancia MagnØtica Nuclear, Universidad Complutense; Madrid, Spain) with the signal of the residual nondeuterated solvent as an internal stan- and water (1 mL). The resulting solid was washed with refluxing MeOH for 1 h to complete its purification, leading to compounds 1 a-c, 1 g, 1 h and 1 j-p. All aldehydes used in this work were commercially available, with the exception of b-carboline-1-carbaldehyde [49] and b-carboline-3-carbaldehyde, [50] which were prepared according to literature methods. Compounds 1 a, [51] 1b-c, [52] 1 df, [41] 1 e, [53] 1 l-m, [54] and 1 n [55] were known in the literature, although their analytical characterization was normally incomplete.…”

Section: Experimental Section Chemistrymentioning

confidence: 99%

Discovery of a Class of Diketopiperazines as Antiprion Compounds

et al. 2010

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Prion diseases are fatal neurodegenerative and infectious disorders for which effective pharmacological tools are not yet available. This unmet challenge and the recently proposed interplay between prion diseases and Alzheimer's have led to a more urgent demand for new antiprion agents. Herein, we report the identification of a novel bifunctional diketopiperazine (DKP) derivative 1 d, which exhibits activity in the low micromolar range against prion replication in ScGT1 cells, while showing low cytotoxicity. Supported by properly addressed molecular modeling studies, we hypothesized that a planar conformation is the major determinant for activity in this class of compounds. Moreover, studies aimed at assessing the mechanism-of-action at the molecular level showed that 1 d might interact directly with recombinant prion protein (recPrP) to prevent its conversion to the pathogenic misfolded prion protein (PrP(Sc))-like form. This investigation suggests that DKP based antiprion compounds can serve as a promising lead scaffold in developing new drugs to combat prion diseases.

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Section: Experimental Section Chemistrymentioning

confidence: 99%

Discovery of a Class of Diketopiperazines as Antiprion Compounds

et al. 2010

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“…The resulting solid was washed with refluxing MeOH for 1 h to complete its purification, leading to compounds 1 a – c , 1 g, 1 h and 1 j – p . All aldehydes used in this work were commercially available, with the exception of β‐carboline‐1‐carbaldehyde49 and β‐carboline‐3‐carbaldehyde,50 which were prepared according to literature methods. Compounds 1 a, 51 1b – c, 52 1 d – f ,41 1 e, 53 1 l – m, 54 and 1 n 55 were known in the literature, although their analytical characterization was normally incomplete.…”

Section: Methodsmentioning

confidence: 99%

Jatropha cultivation in southern India: assessing farmers' experiences

Axelsson¹,

Franzén²,

Ostwald³

et al. 2012

Biofuels Bioprod Bioref

287

105

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Together with 106 farmers who started growing Jatropha (Jatropha curcas L.) in 2004–2006, this research sought to increase the knowledge around the real‐life experience of Jatropha farming in the southern India states of Tamil Nadu and Andhra Pradesh. Launched as an alternative for diesel in India, Jatropha has been promoted as a non‐edible plant that could grow on poor soils, yield oil‐rich seeds for production of bio‐diesel, and not compete directly with food production. Through interviews with the farmers, information was gathered regarding their socio‐economic situation, the implementation and performance of their Jatropha plantations, and their reasons for continuing or discontinuing Jatropha cultivation. Results reveal that 82% of the farmers had substituted former cropland for their Jatropha cultivation. By 2010, 85% (n = 90) of the farmers who cultivated Jatropha in 2004 had stopped. Cultivating the crop did not give the economic returns the farmers anticipated, mainly due to a lack of information about the crop and its maintenance during cultivation and due to water scarcity. A majority of the farmers irrigated and applied fertilizer, and even pesticides. Many problems experienced by the farmers were due to limited knowledge about cultivating Jatropha caused by poor planning and implementation of the national Jatropha program. Extension services, subsidies, and other support were not provided as promised. The farmers who continued cultivation had means of income other than Jatropha and held hopes of a future Jatropha market. The lack of market structures, such as purchase agreements and buyers, as well as a low retail price for the seeds, were frequently stated as barriers to Jatropha cultivation. For Jatropha biodiesel to perform well, efforts are needed to improve yield levels and stability through genetic improvements and drought tolerance, as well as agriculture extension services to support adoption of the crop. Government programs will ‐probably be more effective if implementing biodiesel production is conjoined with stimulating the demand for Jatropha biodiesel. To avoid food‐biofuel competition, additional measures may be needed such as land‐use restrictions for Jatropha producers and taxes on biofuels or biofuel feedstocks to improve the competitiveness of the food sector compared to the bioenergy sector. © 2012 Society of Chemical Industry and John Wiley & Sons, Ltd

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“…The resulting 5-azidocanthin-6-one was further transformed to 5-aminocanthin-6-one via catalytic reduction (Figure 6). Suzuki et al [39] reported the synthesis of canthin-6-one derivative from 1-formyl-9H-β-carboline and its 4-methoxy derivative. In addition many researchers are continuous trying to do more research in this field.…”

Section: Synthesis Of β-Carbolinementioning

confidence: 99%

Design and Strategic Synthesis of Some β-Carboline-Based Novel Natural Products of Biological Importance

Chundawat¹

2019

Organic Synthesis [Working Title]

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β-Carboline compounds and their derivatives have attracted strong interest in medicinal chemistry due to their biological and pharmacological properties. Many bioactive β-carboline-based natural products have been found to be an important source of drugs and drug leads. β-Carboline has major players in natural products chemistry, which plays an important role in drug discovery. β-Carboline represents the core unit of several natural products, alkaloids, and bioactive compounds. The unusual and complex molecular architectures of natural products pose significant challenges to organic chemists and are a source of inspiration for the development of new organic reactions and innovative synthetic strategies. However, in many cases, β-carboline natural products are isolated in only minute quantities, and their constant supply from natural sources is problematic or virtually impossible. In addition, chemoselective derivatization of natural products themselves is usually quite difficult because of their sensitive and elaborate molecular structures, and access to their structural analogs is severely restricted in many cases. Since chemical synthesis is expected to be the only way to overcome these shortcomings, β-carboline natural products are rewarding synthetic targets for organic chemists. This chapter assimilates the reports pertaining to the synthetic applications of some β-carbolines for the synthesis of substituted and fused β-carbolines.

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A Total Synthesis of 1-Methoxycanthin-6-one: An Efficient One-Pot Synthesis of the Canthin-6-one Skeleton from β-Carboline-1-carbaldehyde

Cited by 23 publications

References 9 publications

Discovery of a Class of Diketopiperazines as Antiprion Compounds

Discovery of a Class of Diketopiperazines as Antiprion Compounds

Jatropha cultivation in southern India: assessing farmers' experiences

Design and Strategic Synthesis of Some β-Carboline-Based Novel Natural Products of Biological Importance

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