First Enantiospecific Synthesis of (−)-Parvifoline and (−)-Curcuquinone

Thakkar, Mahesh; Jogdand, Ganesh F.; Kalkote, Uttam R.

doi:10.1021/jo061730d

Cited by 38 publications

(16 citation statements)

References 20 publications

(25 reference statements)

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“…The molecular formula of 12,13-epoxyparvifoline ( 5 The HRESIMS data of 12,13-epoxyparvifoline benzoate (6) also showed a lithium adduct molecular ion at m/z 337.1801 (calcd as 337.1798 for [C 22 H 24 O 3 + Li] + ). The 1 H and 13 C NMR spectra showed patterns similar to those of 5 (Tables 1 and 2). The H-1 and H-4 atoms were shifted at higher frequencies with respect to 5.…”

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confidence: 74%

Parvifoline Derivatives as Tubulin Polymerization Inhibitors

et al. 2019

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A series of functionalized sesquiterpenoids derived from benzocyclooctene, including natural parvifoline (1), isoparvifoline (3), epoxyparvifoline (5), epoxyisoparvifoline (7), 8,12-oxyparfivoline (9), 8,14-oxyparvifoline (11), and the respective benzoyl derivatives 2, 4, 6, 8, 10, and 12, were prepared and tested for their inhibitory effect on the in vitro α,β-tubulin polymerization process. The structural analysis and characterization of the new compounds 5–7 and 9–12 were achieved by 1D and 2D NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis of 6, 7, and 9. Preparation of 9 and 12 involved molecular rearrangements of the epoxide group with transannular 1,5-hydride shifts. At 10 μM compounds 1, 5, and 8 inhibited the polymerization of the α,β-tubulin heterodimer by 24%, 49%, and 90% as compared to colchicine. These compounds were subjected to docking analysis that supported their interactions in a colchicine binding site located in the α-tubulin subunit, in the pocket formed by Phe296, Pro298, Pro307, His309, Tyr312, Lys338, Thr340, Ile341, and Gln342. Competitive inhibition assays with colchicine were also performed for the three compounds, which supported their binding at the colchicine secondary site in α-tubulin. Also, evaluations of their cytotoxicity on MCF7 breast carcinoma, HeLa cervix carcinoma, and HCT 116 colon carcinoma cell lines were carried out and showed that 8 is active against the HeLa and HCT 116 cell lines with IC50 3.3 ± 0.2 and 5.0 ± 0.5 μM, respectively.

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confidence: 74%

Parvifoline Derivatives as Tubulin Polymerization Inhibitors

et al. 2019

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“…96 The first enantioselective synthesis of (−)-parvifoline and (−)-curcuquinone has been reported. 97 6 Sesquicamphane, cyclosesquicamphane, campherenane, fumagillane and petasitane Syntheses of two (E)-endo-bergamoten-12-oic acid derivatives have been reported. 98 Three new campherenane, 115, 116 and 119, and three new santalane sesquiterpenes 121-123, with bioactive properties, have been isolated from Santalum album of Indian origin.…”

Section: Bicyclofarnesanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2007

Nat. Prod. Rep.

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“…In connection with an ongoing program of the synthesis of biogically active natural products using ring-closing metathesis, we have already shown its effectiveness in construction of the D ring of camptothecin [8] and parvifoline. [9] Herein we describe an efficient four-step synthesis of pulchellalactam 1 from commercially available and inexpensive methallyl chloride 2 employing ring-closing metathesis as a key step (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%