Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum

Murata, Chihiro; Ogura, Tetsuhiro; Narita, Shuhei; Kondo, Anna P.; Iwasaki, Natsumi; Saito, Tamao; Usuki, Toyonobu

doi:10.1016/j.bmcl.2016.01.067

Cited by 10 publications

(14 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At 20–80 µM, MPBD dose-dependently suppresses the growth of human leukemia K562 and HL-60 cells in vitro [28]. In addition, MPBD and its synthetic derivatives possess antimicrobial activities against Escherichia coli and Bacillus subtilis [111].…”

Section: Novel Biologically Active Compounds Found In Cellular Slimentioning

confidence: 99%

Dictyostelium: An Important Source of Structural and Functional Diversity in Drug Discovery

Kubohara

Kikuchi

2018

Cells

View full text Add to dashboard Cite

The cellular slime mold Dictyostelium discoideum is an excellent model organism for the study of cell and developmental biology because of its simple life cycle and ease of use. Recent findings suggest that Dictyostelium and possibly other genera of cellular slime molds, are potential sources of novel lead compounds for pharmacological and medical research. In this review, we present supporting evidence that cellular slime molds are an untapped source of lead compounds by examining the discovery and functions of polyketide differentiation-inducing factor-1, a compound that was originally isolated as an inducer of stalk-cell differentiation in D. discoideum and, together with its derivatives, is now a promising lead compound for drug discovery in several areas. We also review other novel compounds, including secondary metabolites, that have been isolated from cellular slime molds.

show abstract

Section: Novel Biologically Active Compounds Found In Cellular Slimentioning

confidence: 99%

Dictyostelium: An Important Source of Structural and Functional Diversity in Drug Discovery

Kubohara

Kikuchi

2018

Cells

View full text Add to dashboard Cite

show abstract

“…By following the known procedures, monoiodination of the commercially available methyl 3,5-dimethoxybenzoate, 3,5-dimethoxybenzaldehyde, and 3,5-dimethoxybenzyl alcohol under the influence of either I 2 /silver trifluoroacetate or N -iodosuccinimide afforded 1 [32–34], 2 [35], and 7 [36–37], respectively (Scheme 2). The hydroxy group of 7 was protected as an acetate, providing 3 in 96% yield.…”

Section: Resultsmentioning

confidence: 99%

Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

Jung

Singh

Kim

2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.

show abstract

“…By contrast, the synthesis of Murata et al . (Scheme b) started from 3,5‐dihydroxybenzoic acid 15 and required the installation of the pentyl side chain, which resulted in synthetic route with a larger number of linear steps (compared to that of Saito et al …”

Section: Substituted Phenyl Compoundsmentioning

confidence: 95%

“…By contrast, the synthesis of Murata et al [20] (Scheme 3b) started from 3,5-dihydroxybenzoic acid 15 and required the installation of the pentyl side chain, which resulted in synthetic route with al arger number of linear steps (compared to that of Saito et al [19] ). Thus, acid 15 was methylated with dimethyl sulfate, followed by reduction with lithium aluminum hydride to yield alcohol 17.R egioselective iodination with N-iodosuccinimide (NIS) afforded iodobenzene 18.I nstallation of the pentyl side chain was achieved by aW ittig reaction.…”

Section: Dictyoquinonementioning

confidence: 96%

Natural Products from Social Amoebae

Barnett

Stallforth

2017

Chemistry A European J

View full text Add to dashboard Cite

Natural products are invaluable sources of structural diversity and complexity ideally suited for the development of therapeutic agents. The search for novel bioactive molecules has prompted scientists to explore various ecological niches. Microorganisms have been shown to constitute such an important source. Despite their biosynthetic potential, social amoebae, that is, microorganisms with both a uni- and multicellular lifestyle, are underexplored regarding their secreted secondary metabolome. In this review, we present the structural diversity of amoebal natural products and discuss their biological functions as well as their total syntheses.

show abstract

Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum

Cited by 10 publications

References 24 publications

Dictyostelium: An Important Source of Structural and Functional Diversity in Drug Discovery

Dictyostelium: An Important Source of Structural and Functional Diversity in Drug Discovery

Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

Natural Products from Social Amoebae

Contact Info

Product

Resources

About