Progress toward the Total Synthesis of Lucentamycin A: Total Synthesis and Biological Evaluation of 8-<i>epi</i>-Lucentamycin A

Daniels, R. Nathan; Melancon, Bruce J.; Wang, Emily A.; Crews, Brenda C.; Marnett, Lawrence J.; Sulikowski, Gary A.; Lindsley, Craig W.

doi:10.1021/jo902115s

Cited by 25 publications

(16 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Apart from the reports on the biological synthesis of Lucentamycin A, chemical methods of synthesizing it have also been developed (Daniels et al . ; Ranatunga et al . ).…”

Section: Anticancer and Antitumour Compoundsmentioning

confidence: 99%

“…The same culture of N. lucentensis was also found to produce another related compound, Lucentamycin E that was structurally similar to Lucentamycin B . Apart from the reports on the biological synthesis of Lucentamycin A, chemical methods of synthesizing it have also been developed (Daniels et al 2009;Ranatunga et al 2012).…”

Section: Anticancer and Antitumour Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Nocardiopsisspecies: a potential source of bioactive compounds

et al. 2015

View full text Add to dashboard Cite

Summary Members of the genus Nocardiopsis are an ecologically versatile and biotechnologically important group of Actinomycetes. Most of the isolates are halotolerant or halophilic and they prevail in soils, marine environments or hypersaline locations. To aid their survival under these conditions, they mainly produce extremozymes, compatible solutes, surfactants and bioactive compounds. The current review details the bioactive compounds obtained for this genus. Important antimicrobial agents obtained from this genus include polyketides, phenzines, quinoline alkaloids, terphenyls, proteins, thiopeptides and amines. Polyketides and peptides displaying potent anticancer activities are also significant. Tumour promoting agents, P‐glycoprotein (P‐gp) inhibitors, immunomodulators and protein kinase inhibitors are other relevant products obtained from Nocardiopsis species. Structurally, polyketides (synthesized by polyketide synthases) and peptides (made by nonribosomal peptide synthetases or cyclodipeptide synthases) are important compounds. Considered here are also toxins, anti photoaging and adipogenic agents produced by this genus. The gene clusters mediating the synthesis of bioactive compounds have been described. Commercially available products (Apoptolidins and K‐252a) derived from this genus have also been described. This review highlights the significance of a single genus in producing an assortment of compounds with varied biological activities. On account of these features, the members of this genus have established a place for themselves and are of considerable value in producing compounds with profound bio‐medical applications.

show abstract

“…Apart from the reports on the biological synthesis of Lucentamycin A, chemical methods of synthesizing it have also been developed (Daniels et al . ; Ranatunga et al . ).…”

Section: Anticancer and Antitumour Compoundsmentioning

confidence: 99%

Section: Anticancer and Antitumour Compoundsmentioning

confidence: 99%

Nocardiopsisspecies: a potential source of bioactive compounds

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Albericio and co-workers [18] reported a rapid and high-yielding synthesis of (E)-barmumycin (65). They started the synthesis from isobutyl but-3-enoate (66), which was converted into the bromoketone 67 in two steps. N-Alkylation of 68 with 67 under MW irradiation gave 69, which was converted into (E)-barmumycin (65) in several steps (Scheme 19.15).…”

Section: Total Synthesis Of Various Classes Of Natural Productsmentioning

confidence: 99%

“…Lucentamycin A (314) displays significant in vitro cytotoxicity against human colon carcinoma and also antibiotic, antifungal, and anticancer activity. Lindsley and co-workers [66] performed the total synthesis of (+)-8-epi-lucentamycin A (315) in 15 steps. Garner's aldehyde (316) was converted into the bicyclic compound 317.…”

Section: Synthesis Of Analogs Of Natural Productsmentioning

confidence: 99%

Microwaves in the Synthesis of Natural Products

Eycken¹,

Bariwal²,

Bariwal³

2012

Microwaves in Organic Synthesis

View full text Add to dashboard Cite

“…23 This surprising result led us to study 7 in our standard HCT116 colon carcinoma cell viability assay. 22-24 Here as well, 7 had no affect on HCT116 cell viability after 48 hours.…”

mentioning

confidence: 99%

Total Synthesis of (+)-7-Bromotrypargine and Unnatural Analogues: Biological Evaluation Uncovers Activity at CNS Targets of Therapeutic Relevance

Brogan

Stoops

Crews

et al. 2011

ACS Chem. Neurosci.

Self Cite

View full text Add to dashboard Cite

The first total synthesis of (+)-7-bromotrypargine, a β-carboline alkaloid from Ancornia sp. is reported. The synthesis proceeds in 9 steps, 8 steps longest linear sequence, in 36.9% overall yield. Biological characterization found that (+)-7-bromotrypargine is an H3 antagonist, and a selective inhibitor of DAT and NET, without inhibiting SERT. Moreover, unlike electron rich congeners, (+)-7-bromotrypargine is not cytotoxic, and thus represents an attractive starting point for chemical optimization; therefore, we piloted a number of chemistries for the synthesis of unnatural analogs.

show abstract

Progress toward the Total Synthesis of Lucentamycin A: Total Synthesis and Biological Evaluation of 8-epi-Lucentamycin A

Cited by 25 publications

References 17 publications

Nocardiopsisspecies: a potential source of bioactive compounds

Nocardiopsisspecies: a potential source of bioactive compounds

Microwaves in the Synthesis of Natural Products

Total Synthesis of (+)-7-Bromotrypargine and Unnatural Analogues: Biological Evaluation Uncovers Activity at CNS Targets of Therapeutic Relevance

Contact Info

Product

Resources

About