Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

Eyong, Kenneth O.; Kumar, P. B. Sunil; Kuete, Victor; Folefoc, Gabriel N.; Nkengfack, Ephriam A.; Baskaran, Sundarababu

doi:10.1016/j.bmcl.2008.09.053

Cited by 79 publications

(46 citation statements)

References 26 publications

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“…It is worth noting that as in our previous study (Eyong et al, 2008) the acetylation of the aldehyde 4 with acetic anhydride in pyridine gave the monoacetate 5 whereas the acetylation of lapachol 1 under the same conditions afforded a mixture of dehydro a-and b-lapachone diacetates 6a and 6b (Manners et al, 1975) as the major products. The acetylation of both compounds 1 and 4 involves an enol intermediate, which could be explained by the mechanism below (Scheme 2).…”

Section: Resultsmentioning

confidence: 93%

“…The synthesis of these compounds has been the object of recent chemical studies (Claessens et al, 2010). Lapachol, the principal precursor of pyranonaphthoquinones and several compounds derived from lapachol have already been pharmacologically evaluated (Da Silva et al, 2002;Dos Santos et al, 2000;Guiraud et al, 1994), and found to exhibit a broad spectrum of biological activities (Eyong et al, 2008). Thus, derivatives from lapachol could be useful for the development of new drug candidates.…”

Section: Introductionmentioning

confidence: 99%

“…From our previous studies on lapachol, (Eyong et al, 2008) the anti-cancer agent: 2-acetylfuranonaphthoquinone was obtained during ozonolysis on lapachol suggesting that radical cyclisation was involved. In an effort to study the mechanism of its formation, lapachol was subjected to various free radical initiators such as DDQ, CAN, UV radiation and Cobalt acetate.…”

Section: Introductionmentioning

confidence: 99%

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Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol

et al. 2011

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The synthesis of 2-hydroxy-2-(3-methylbut-2-enyl)-2H-indene-1,3-dione 3, from lapachol which involves a ring contraction via the Hooker intermediate 1,2-dihydroxy-2-(3-methylbut-2-en-1-yl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid 2 is described. Different pyranonaphthoquinone derivatives, obtained in our previous synthetic work, were screened for antimycobacterial (Mycobacterium tuberculosis) activity and against resistant strains of Gram-positive (Bacillus cereus and Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. The results indicated significant activity of all the tested samples against M. tuberculosis and only moderate activity against the Gram-positive and Gram-negative bacteria.

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Section: Resultsmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol

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“…[3][4][5][6] Previous phytochemical investigations of Tabebuia plants resulted in the isolation and characterization of a variety of furonaphthoquinones bearing a methoxy group in the benzene ring. [7][8][9] Thus, these methoxylated furonaphthoquinones were confirmed to be characteristic constituents of Tabebuia plants.…”

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Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from <i>Tabebuia</i> Plants

et al. 2013

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Furonaphthoquinones are promising skeletons for anticancer drug molecules. In particular, methoxylated furonaphthoquinones are characteristic constituents of Tabebuia plants. In this research, we synthesized the furonaphthoquinones by effective one-pot cascade reactions of 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenides with 3-butyn-2-ol in the presence of palladium and cuprous catalysts via Sonogashira coupling and intramolecular cyclization. Furthermore, we demonstrated that the synthetic furonaphthoquinones showed moderate cytotoxicity against human leukemia U937 and HL-60 cells. Our work highlights the importance of furonaphthoquinones as antileukemic agents.Key words furonaphthoquinone; Tabebuia plant; Sonogashira coupling; antileukemic activity Tabebuia plants belong to the Bignoniaceae family, which is commonly found in North and South America. The plants have been used for the treatment of cancer as folk medicines, Pau d'Arco, Ipé Roxo, Taheebo, and Lapacho. 1) In 1982, 2-(1-hydroxyethyl) naphtho [2,3-b] furan-4,9-dione FN0-ol and 2-acetylnaphtho[2,3-b] furan-4,9-dione FN0-one were isolated from Tabebuia cassinoides. Both these furonaphthoquinones showed significant activity against human oral epidermoid carcinoma KB cells.2) Subsequently, FN0-one was investigated as an anticancer agent in vitro, and it was found that this quinone shows moderate cytotoxicity against various cancer cell lines, including human oral squamous carcinoma HSC-2, HSC-3, HSC-4, human prostate carcinoma DU-145, human melanoma C8161, human lung adenocarcinoma A549, and human epithelial carcinoma HeLa cells.3-6) Previous phytochemical investigations of Tabebuia plants resulted in the isolation and characterization of a variety of furonaphthoquinones bearing a methoxy group in the benzene ring.7-9) Thus, these methoxylated furonaphthoquinones were confirmed to be characteristic constituents of Tabebuia plants.As described above, furonaphthoquinones are considered interesting natural compounds in biochemical and pharmacological fields. Herein, we report the detailed synthesis of these furonaphthoquinones and their antileukemic activity. Results and DiscussionSome of naturally occurring furonaphthoquinones bear a 1-hydroxyethyl group at the C2-position. Kobayashi et al. reported a synthesis method of furonaphthoquinones based on sequential coupling/ring closure reactions.10) However, the reaction with intact 3-butyn-2-ol was unsuccessful. Thus, we attempted to improve their method, with the aim of making it useful for the synthesis of a wide variety of the compounds having a hydroxy group. 2-(1-Hydroxyethyl)-furonaphthoquinones such as FN0-ol are envisaged to be formed through the in situ generation of iodonaphthoquinones from phenyliodonium ylides in the presence of cuprous oxide (Cu 2 O), followed by Sonogashira coupling with acetylene and subsequent intramolecular cyclization. The phenyliodonium ylide 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide IY0, which would serve as a suitable precursor for the su...

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“…Antitumor activities of compounds 1 -3 were evaluated in vitro by using a variety of cultured cancer cell lines (P-388 and HL-60 (by the MTT (thiazolyl blue tetrazolium bromide) method [12], and A-549 and BEL-7402 by the SRB (sulforhodamine B) method [13]). The results are summarized in Fig.…”

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A New Nortriterpene from the Root of Celastrus hypoleucus

Wang

Tian

Ying

2010

Helvetica Chimica Acta

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A new nortriterpene, 2-hydroxy-3-methyl-21-oxo-12,24-dinor-D : B-friedooleana-1,3,5(10),7-tetraen-29-oic acid (1), was isolated from the root of Celastrus hypoleucus, together with the two known compounds, celastorol (2) and pristimerine (3). Their structures were elucidated on the basis of spectroscopic analyses. Compounds 1 -3 exhibited in vitro significant antioxidant (against lipid peroxidation; by the TBARS method) and antitumor activities (against cancer cell lines P-388, A-549, HL-60, and BEL-7402).Introduction. -Celastrus hypoleucus (Oliv. ) Warb. is a species of the Celastraceae family and commonly named as Nan She Teng (Chinese trade name). It is widely distributed in China and has been used for the treatment of inflammation and detumescence. As part of our continuing investigation of bioactive components from the Celastraceae family [1 -7], many new antioxidant and antitumor-active metabolites have been isolated and characterized from C. hypoleucus [1] [6] [7]. In this article, we report a new nortriterpene, 2-hydroxy-3-methyl-21-oxo-12,24-dinor-D : B-friedooleana-1,3,5(10),7-tetraen-29-oic acid 1 ) (1), and two known triterpenes, i.e., celastorol (2) [8] and pristimerine (3) [9], from the root of C. hypoleucus (Fig. 1). In addition, their antioxidant and antitumor activities were investigated.

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Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

Cited by 79 publications

References 26 publications

Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol

Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol

Synthesis and Cytotoxicity on Human Leukemia Cells of Furonaphthoquinones Isolated from <i>Tabebuia</i> Plants

A New Nortriterpene from the Root of Celastrus hypoleucus

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