Total Synthesis of the Proposed Structures of Indole Alkaloids Lyaline and Lyadine

Bennasar, M.‐Lluïsa; Roca, Tomas; Monerris, Manuel

doi:10.1021/jo035507h

Cited by 18 publications

(16 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 1 H-NMR and 13 C-NMR of Compound 14 are consistent with those reported in the previous study, so it was concluded that Compound 14 is 5-(1′-hydroxyethyl) nicotinic acid methyl ester [ 27 ].…”

Section: Methodssupporting

confidence: 83%

Synthesis and Promotion of the Osteoblast Proliferation Effect of Morroniside Derivatives

Han

et al. 2018

Molecules

View full text Add to dashboard Cite

Sambucus williamsii Hance has been used in fractures for thousands of years, but research on its active components, such as morroniside, until now had not been carried out. In this study, morroniside was taken as the leading compound, and fourteen derivatives were synthesized. The promotion of osteoblast proliferation effect of the derivatives was evaluated on MC3T3-E1 cells. Five derivatives (2, 3, 4, 5, and 14) showed a good proliferation effect on MC3T3-E1 cells, and their promoted expression effects on OC (Osteocalcin) and ALP (Alkaline phosphatase) in MC3T3-E1 cells were measured. Compound 3 was shown to have the strongest proliferation effect (EC50 = 14.78 ± 1.17 μg/mL) and to significantly promote the expression of OC and ALP.

show abstract

Section: Methodssupporting

confidence: 83%

Synthesis and Promotion of the Osteoblast Proliferation Effect of Morroniside Derivatives

Han

et al. 2018

Molecules

View full text Add to dashboard Cite

show abstract

“…The trivial names of the same molecules are given in Figure B. As with any analysis of this type, it does assume that the structures are correct, and, for instance, at least that for lyaline (left‐hand‐most structure, marked green) is in doubt . However, we do not rehearse these in further detail, save to mention that the largest cluster contains a great many sterols, molecules that were among the most abundant both in terms of approved drugs and of endogenous metabolites …”

Section: Resultsmentioning

confidence: 98%

Analysing and Navigating Natural Products Space for Generating Small, Diverse, But Representative Chemical Libraries

O’Hagan

Kell

2017

Biotechnology Journal

View full text Add to dashboard Cite

Armed with the digital availability of two natural products libraries, amounting to some 195 885 molecular entities, we ask the question of how we can best sample from them to maximize their "representativeness" in smaller and more usable libraries of 96, 384, 1152, and 1920 molecules. The term "representativeness" is intended to include diversity, but for numerical reasons (and the likelihood of being able to perform a QSAR) it is necessary to focus on areas of chemical space that are more highly populated. Encoding chemical structures as fingerprints using the RDKit "patterned" algorithm, we first assess the granularity of the natural products space using a simple clustering algorithm, showing that there are major regions of "denseness" but also a great many very sparsely populated areas. We then apply a "hybrid" hierarchical K-means clustering algorithm to the data to produce more statistically robust clusters from which representative and appropriate numbers of samples may be chosen. There is necessarily again a trade-off between cluster size and cluster number, but within these constraints, libraries containing 384 or 1152 molecules can be found that come from clusters that represent some 18 and 30% of the whole chemical space, with cluster sizes of, respectively, 50 and 27 or above, just about sufficient to perform a QSAR. By using the online availability of molecules via the Molport system (www.molport.com), we are also able to construct (and, for the first time, provide the contents of ) a small virtual library of available molecules that provided effective coverage of the chemical space described. Consistent with this, the average molecular similarities of the contents of the libraries developed is considerably smaller than is that of the original libraries. The suggested libraries may have use in molecular or phenotypic screening, including for determining possible transporter substrates.

show abstract

“…Later Gatta and co-workers [34] reported an improved synthesis of methyl 1-formyl-9-H-pyrido [3,4-b] indole-3-carboxylate from 1-methyl-3methoxycarbonyl-β-carboline via oxidation with SeO 2 in dioxane. These workers further reported the application of 1-formyl-9H-β-carboline for the synthesis of canthin-6-one [35].…”

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]

View full text Add to dashboard Cite

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.

show abstract

Total Synthesis of the Proposed Structures of Indole Alkaloids Lyaline and Lyadine

Cited by 18 publications

References 17 publications

Synthesis and Promotion of the Osteoblast Proliferation Effect of Morroniside Derivatives

Synthesis and Promotion of the Osteoblast Proliferation Effect of Morroniside Derivatives

Analysing and Navigating Natural Products Space for Generating Small, Diverse, But Representative Chemical Libraries

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

Contact Info

Product

Resources

About