25932-95-0Relevant academic research and scientific papers
Cytotoxicity of Synthesized 1,4-Naphthoquinone Oxime Derivatives on Selected Human Cancer Cell Lines
Zhang, Qijing,Dong, Jinyun,Cui, Jiahua,Huang, Guang,Meng, Qingqing,Li, Shaoshun
, p. 612 - 619 (2018)
In an effort to develop potent and selective antitumor agents, a series of 1,4-naphthoquinone oxime derivatives were designed and synthesized. The cytotoxicity of these compounds were evaluated against five human cancer cell lines (colorectal cancer cell: HCT-15, breast cancer cell: MDA-MB-231, liver cancer cell: BEL-7402, colorectal cancer cell: HCT-116 and ovarian cancer cell: A2780) in vitro. Among them, compound 14 was found to be the most potent cytotoxic compound against three cell lines (MDA-MB-231, BEL-7402 and A2780) with IC50 values of 0.66±0.05, 5.11±0.12 and 8.26±0.22μM, respectively. Additionally, the length of the side chains and the position of the substituent may also affect the cytotoxic activity of the naphthoquinone oxime derivatives. In general, compound 14 effectively inhibited breast cancer cell proliferation and may become a promising anticancer agent.
A regioselective synthesis of 7-methyl juglone and its derivatives
Cui, Jiahua,Li, Shaoshun,Jia, Jinping
supporting information, p. 18 - 25 (2020/05/14)
7-Methyl juglone as a naturally occurring naphthoquinone showed striking antibacterial, antifungal, antivirus and anticancer activity. Its derivatives had also been characterized as key intermediates in the preparation of natural naphthoquinones and anthraquinones. Herein, we reported a regioselective synthesis of 7-methyl juglone via the construction of fused polycyclic systems. The key steps of the strategy involved Stobbe condensation of 2,5-dimethoxy benzaldehyde with diethyl succinate, intramolecular cyclization, reduction, acid-facilitated debenzylation and further cerium(IV) ammonium nitrate-mediated oxidation. Compared with the reported methods employing Birch conditions in liquid ammonia or Friedel-Crafts cycloacylation with melting heat of aluminum salts, the reaction conditions in the new synthetic route were milder and suitable for large scale preparations. In addition, all of the starting materials in the synthesis were readily available. It has great implications for the design and synthesis of structurally asymmetric naphthoquinones derivatives.
Model study toward total synthesis of dimeric pyranonaphthoquinones: Synthesis of hemi-actinorhodin#
Ando, Yoshio,Fukazawa, Takumi,Ohmori, Ken,Suzuki, Keisuke
supporting information, p. 1364 - 1376 (2021/05/17)
In connection with our synthetic study toward the dimeric pyranonaphthoquinone antibiotics, actinorhodin (1) and β-naphthocyclinone (3), we describe herein the synthesis of a monomer, hemi-actinorhodin (6) as a model target. Several implications were gained, including (1) stereoselective synthesis of the pyranonaphthoquinone, (2) viable construction of the naphthazarin core, and (3) the final deprotection conditions.
Benzimidazole Derivatives as Novel Zika Virus Inhibitors
Anh, Le Duc,De, Tran Quang,Duc Thanh, Danh La,Dupont-Rouzeyrol, Myrielle,Grailhe, Regis,Hue, Bui Thi Buu,Jo, Eunji,Nguyen, Phuong Hong,Son, Nguyen Hoang,Thoa, Than Thi,Van Hieu, Mai,Van Tuan, Nguyen,Windisch, Marc P.
supporting information, p. 1453 - 1463 (2020/05/25)
We have synthesized 50 benzimidazole (BMZ) derivatives with 1,2-phenylenediamines and aromatic aldehydes under mild oxidation conditions by using inexpensive, nontoxic inorganic salt sodium metabisulfite in a one-pot condensation reaction and screened their ability to interfere with Zika virus (ZIKV) infection utilizing a cell-based phenotypic assay. Seven BMZs inhibited an African ZIKV strain with a selectivity index (SI=CC50/EC50) of 9–37. Structure-activity relationship analysis demonstrated that substitution at the C-2, N-1, and C-5 positions of the BMZ ring were important for anti-ZIKV activity. The hybrid structure of BMZ and naphthalene rings was a structural feature responsible for the high anti-ZIKV activity. Importantly, BMZs inhibited ZIKV in human neural stem cells, a physiologically relevant system considering the severe congenital anomalies, like microcephaly, caused by ZIKV infection. Compound 39 displayed the highest antiviral efficacy against the African ZIKV strain in Huh-7 (SI>37) and neural stem cells (SI=12). Compound 35 possessed the highest activity in Vero cells (SI=115). Together, our data indicate that BMZs derivatives have to be considered for the development of ZIKV therapeutic interventions.
Total Synthesis of the Antitumor-Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer
Pullella, Glenn A.,Vuong, Daniel,Lacey, Ernest,Piggott, Matthew J.
supporting information, p. 3623 - 3634 (2021/01/09)
The 2,6′-bijuglone natural product diospyrin and its unnatural 3,6′-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methylju
Synthetic method of 7-methyljuglone
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Paragraph 0033-0036, (2020/03/06)
The invention discloses a synthetic method of 7-methyljuglone. The method comprises the steps: taking 2,5-dialkoxy benzaldehyde (II) as a raw material, adopting a method of carrying out a condensationreaction on aldehyde and succinate of linear alkyl alcohol in the presence of sodium hydrogen and cyclizing the condensation product in a sodium acetate-acetic anhydride system, to prepare an intermediate 4-acetoxy-5,8-dialkoxy-2-naphthoate derivative (III); reducing the intermediate through lithium aluminum hydride, dissolving in an organic solvent, and carrying out a dehydroxylation reaction under the catalytic action of a catalyst to generate an intermediate 5,8-dialkoxy-3-methyl-1-naphthol (V); and carrying out methoxy methyl ether (MOM) protection, ceric ammonium nitrate oxidation and deprotection reaction on the intermediate (V) to generate 7-methyljuglone. The synthetic method is simple and convenient and good in effect; the used raw materials are easy to obtain and low in price; the reaction yield of each step is high, the conditions are mild, and the method is suitable for large-scale preparation.
Synthesis and bioevaluation of shikonin derivatives
Cao, Sufen,Zhang, Jiangang,Duan, Wenhu
, p. 945 - 950 (2018/08/17)
Background: Ester and amide derivatives of shikonin were synthesized to improve the chemical stability of shikonin. Methods: All synthesized compounds were evaluated for their antiproliferative activity against A549 cell line by SRB assay, and five of them demonstrated comparable cytotoxicity to shikonin. Results and Conclusion: The most potent compound, 22d, was more stable and potent than shikonin.
General synthesis route to benanomicin-pradimicin antibiotics
Tamiya, Minora,Ohmori, Ken,Kitamura, Mitsuru,Kato, Hirohisa,Arai, Tadamasa,Oorui, Mami,Suzuki, Keisuke
, p. 9791 - 9823 (2008/09/18)
A general approach to the regio- and stereoselective total synthesis of the benanomicin-pradimicin antibiotics (BpAs) is described. Construction of the aglycon has been achieved by 1)the diastereoselective ring-opening of a biaryl lactone by using (R)-val
Base- and light-assisted synthesis of anthracenes from 3-allylnaphthalene- 2-carbaldehydes
De Koning, Charles B.,Manzini, Sunnyboy S.,Michael, Joseph P.,Mmutlane, Edwin M.,Tshabidi, Tefo R.,Van Otterlo, Willem A.L.
, p. 555 - 564 (2007/10/03)
The synthesis of substituted anthracenes from naphthalene precursors is described. The key step involved heating ortho-allyl substituted naphthalene-2-carbaldehydes and potassium t-butoxide in DMF with concomitant irradiation from a high pressure mercury
Synthesis of hydroxylated naphthoquinone derivatives
Couladouros, Elias A.,Strongilos, Alexandros T.
, p. 3341 - 3350 (2007/10/03)
The use of the Stobbe condensation for the synthesis of juglone derivatives is presented, together with studies towards their further functionalization. The regiospecific oxidation of the above products to o- or p-naphthoquinones was also investigated. Finally, the preparation of useful intermediates for the synthesis of related natural products such as alkannin and shikonin is proposed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
