Total Syntheses of (±)-Hymenolin and (±)-Parthenin

Shimoma, Fumito; Kusaka, Haruhiko; Azami, Hidenori; Wada, Katsuhiko T.; Suzuki, Toshio; Hagiwara, Hisahiro; Ando, Masayoshi

doi:10.1021/jo972077k

Cited by 19 publications

(15 citation statements)

References 22 publications

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“…This structure elucidation has been completed by analysis of its single-crystal X-ray diffraction [140], as supported later by total synthesis of the compound (Scheme 13 ) [141, 142]. …”

Section: Analogues Of Thapsigargin Without Ester Groups Showing Pomentioning

confidence: 99%

Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones

Ren¹,

Yu²,

Kinghorn

2016

CMC

134

121

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Sesquiterpene lactones are of considerable interest due to their potent bioactivities, including cancer cell cytotoxicity and antineoplastic efficacy in in vivo studies. Among these compounds, artesunate, dimethylaminoparthenolide, and L12ADT peptide prodrug, a derivative of thapsigargin, are being evaluated in current cancer clinical or preclinical trials. Based on the structures of several antitumor sesquiterpene lactones, a number of analogues showing greater potency have been either isolated as natural products or partially synthesized, and some potential anticancer agents that have emerged from this group of lead compounds have been investigated extensively. The present review focuses on artemisinin, parthenolide, thapsigargin, and their naturally occurring or synthetic analogues showing potential anticancer activity. This provides an overview of the advances in the development of these types of sesquiterpene lactones as potential anticancer agents, including their structural characterization, synthesis and synthetic modification, and antitumor potential, with the mechanism of action and structure-activity relationships also discussed. It is hoped that this will be helpful in stimulating the further interest in developing sesquiterpene lactones and their derivatives as new anticancer agents.

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“…This structure elucidation has been completed by analysis of its single-crystal X-ray diffraction [140], as supported later by total synthesis of the compound (Scheme 13 ) [141, 142]. …”

Section: Analogues Of Thapsigargin Without Ester Groups Showing Pomentioning

confidence: 99%

Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones

Ren¹,

Yu²,

Kinghorn

2016

CMC

134

121

View full text Add to dashboard Cite

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“…The interaction energy was defined as the difference between the sum of the energy of individual host and guest molecule and the energy of the inclusion complex. 28 We tried several MC runs for searching lowest energy configuration. Figure 2 and 3 show low energy configuration families among the inclusion complexes of β-CD and am-β-CD with MTPA.…”

Section: Resultsmentioning

confidence: 99%

Molecular Modeling of Enantio-discrimination of α-Methoxy-α-trifluoromethylphenylacetic Acid (MTPA) by Cyclomaltoheptaose (β-Cyclodextrin) and 6-Amino-6-deoxy-cyclomaltoheptaose

Jung¹,

Jeong²,

Lee³

et al. 2003

Bulletin of the Korean Chemical Society

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Molecular modeling was performed to comprehend the chiral recognition of α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) enantiomers by cyclomaltoheptaose (β-cyclodextrin, β-CD) and 6-amino-6-deoxycyclomaltoheptaose (am-β-CD). Monte Carlo (MC) docking coupled to constant temperature molecular dynamics (MD) simulations was applied to the investigation for the α-methoxy-α-trifluoromethylphenylacetic acid complexation with two different CDs in terms of the relative distribution of the interaction energies. The calculated results are finely correlated with the experimental observations in chiral recognition thermodynamics. Am-β-CD as a host showed the superior enantio-discrimination ability to the native β-CD where the amino group of am-β-CD was critically involved in enhancing the ability of chiral discrimination via the Coulombic interaction with MTPA.

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“…Shimoma et al [28] reported the regio-and stereoselective synthesis of common synthetic intermediates via kinetic resolution with Lipase PS, (Fig. (4)).…”

Section: Herbicidesmentioning

confidence: 96%

“…(12). Enzymatic route to Lysofungin (28), from a commercially available natural product. Optically active 1-phenylethanols 32 [R 1 =H, halo, C1-4 (halo)alkyl, C1-4 (halo) alkoxy; n=1-3] were treated with chloramines to give optically active 1-phenylethoxy amines (R 1, n=same as above), which are useful intermediates for agrochemicals and pharmaceuticals.…”

Section: 3) Of Candidamentioning

confidence: 99%