6258-38-4Relevant articles and documents
Design and synthesis of arylnaphthalene lignan lactone derivatives as potent topoisomerase inhibitors
Chen, Wang,Feng, Zili,Hu, Daihua,Meng, Jin
, p. 856 - 865 (2021/10/21)
Background: Arylnaphthalene lignan lactones are a class of natural products containing the phenyl-naphthyl skeleton. Some arylnaphthalene lignan lactones have been used in clinical practice as antitumor agents, due to their cytotoxicity and inhibitory activities against DNA topoisomerase I (Topo I) and topoisomerase II (Topo II). Objective: This study presents the design and synthesis of arylnaphthalene lignan lactones derivatives. The inhibitory activities against Topo I and Topo IIα and antitumor activities of these compounds were assayed. Methods: A series of arylnaphthalene lignan lactones derivatives have been designed and synthesized, using the Diels-Alder reaction and Suzuki reaction as the key steps. Their antiproliferation activities were evaluated by sulforhodamine B assay on human breast cancer MDAMB-231, MDA-MB-435 and human cervical cancer HeLa cells. DNA relaxation assays were employed to examine the inhibitory activity of compounds 1-22 on Topo I and Topo IIα in vitro. Flow cytometry analysis was performed to study the drug effects on cell cycle progressions. Results: Seven compounds exhibited the modest anti-proliferation activity with IC50 values between 1.36 and 20 μM. Compounds 3, 19 and 22 showed potent inhibitory activities with IC50 values less than 1 μM. DNA relaxation assay revealed that compound 22 showed potent inhibitory activity against Topo IIα in vitro. Compound 22 also induced DNA breaks in MDA-MB-435 cells evidenced by comet tails and the accumulation of γ-H2AX foci. The ability of 22 in inducing DNA breaks mediated by Topo IIα resulted in G2/M phase arrest and apoptosis. Conclusion: This work indicates that arylnaphthalene lignan lactones derivatives represent a novel type of Topo IIα inhibitory scaffold for developing new antitumor chemotherapeutic agents.
Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza-analogs
Ourhzif, El-Mahdi,Paris, Arnaud,Abrunhosa-Thomas, Isabelle,Ketatni, El Mostafa,Chalard, Pierre,Khouili, Mostafa,Daniellou, Richard,Troin, Yves,Akssira, Mohamed
, (2021/02/26)
A concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lignans and aza-analogs was developed. The main objective was to develop synthetic tactics for the creation of the lactone and lactam unit that would give access to an a
Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation
Gudla, Vanajakshi,Balamurugan, Rengarajan
, p. 9919 - 9933 (2012/01/15)
An intramolecular approach to generate compounds containing an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl3 in combination with AgSbF6 works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and retrojusticidin B (Figure presented).
A Garratt-Braverman route to aryl naphthalene lignans
Mondal, Sayantan,Maji, Manasi,Basak, Amit
experimental part, p. 1183 - 1186 (2011/03/21)
A series of aryl naphthalene lignans were prepared in good yields starting from substituted bis-propargyl ethers. The method involved a base-mediated Garratt-Braverman cyclization followed by benzylic oxidation to the lactone. The chemoselectivity in the
Advances in the methodology of a multicomponent synthesis of arylnaphthalene lactones
Foley, Patrick,Eghbali, Nicolas,Anastas, Paul T.
experimental part, p. 888 - 892 (2010/09/05)
Material and energy inefficiencies in total synthesis can arise from a lack of step economy. Multicomponent syntheses have the potential to optimize step economy and, in turn, to minimize not only waste, but also exposure to hazardous chemicals. Therefore, multicomponent syntheses are of immense interest to the field of Green Chemistry. Herein is described a multicomponent synthesis of arylnaphthalene lignan lactones, which are valuable natural products with promising anticancer and antiviral properties. In an effort to improve our previously reported one-pot, multicomponent synthesis an approach using phenylacetylene, phenylpropargyl chloride, carbon dioxide, catalytic silver iodide, and catalytic 18-crown-6 ether was developed. This methodology was then successfully applied to the preparation of dehydrodimethylconidendrin and its regioisomer, dehydrodimethylretroconidendrin.
Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans
Sagar, Kadali S.,Chang, Chia-Chuan,Wang, Wei-Kung,Lin, Jung-Yaw,Lee, Shoei-Sheng
, p. 4045 - 4054 (2007/10/03)
Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepare
Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes
Ramdayal, Frank D.,Kiemle, David J.,LaLonde, Robert T.
, p. 4607 - 4609 (2007/10/03)
Positional preferences for para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,
Photoinduced Molecular Transformations. Part 135. New Synthesis of Taiwanin C and Justicidin E based on a Radical Cascade Process involving β-Scission of Alkoxy Radicals generated from 3- and 8-Aryl-1-ethyl-1,2-dihydrocyclobutanaphthalen-1-ols prepared by Thermolysis of (Z)-tert-...
Kobayashi, Kazuhiro,Kanno, Yoshikazu,Seko, Shinzo,Suginome, Hiroshi
, p. 3111 - 3118 (2007/10/02)
A new general synthesis of naturally occuring phthalide lignans, based on a radical cascade process triggered by a regioselective β-scission of the alkoxy radicals generated by photolysis of the hypoiodites of 8-aryl-1-ethyl-1,2-dihydrocyclobutanaphthalen-1-ols, is described.Two phases are involved in the present synthesis of phthalide lignans; the first is a new general synthesis of tert-butyl 4-aryl-3- and 4-aryl-8-aminonaphthalene-2-carboxylates by an electrocyclic reaction of o-quinonedimethides thermally generated from (Z)-tert-butyl 3-amino-3-(bicycloocta-1,3,5-trien-7-yl)propenoates; the second is a transformation of the protected 4-aryl-3-aminonaphthalene-2-carboxylic acids into the phthalide lignans.This latter phase involves their successive conversions into 3- and 8-arylcyclobutanaphthalen-1(2H)-ones via the formation of a benzyne intermediate, and then into 3- and 8-aryl-1-ethyl-1,2-dihydrocyclobutanaphthalen-1-ols, followed by β-scission of the alkoxy radicals generated by photolysis of their hypoiodites, generated in situ with the mercury(II) oxide-iodine reagent in benzene.Simultaneous syntheses of the naturally occuring phthalide lignans taiwanin C and justicidin E were thus achieved.
Synthetic Experiments in Lignans: Part XI - Use of Pyridinium Chlorochromate as a Regioselective Reagent in the Synthesis of 1-Phenylnaphthalene Lactones
Anjaneyulu, A. S. R.,Sastry, Ch. V. M.,Umasundari, P.,Satyanarayana, P.
, p. 305 - 307 (2007/10/02)
Pyridinium chlorochromate has been found to be a regioselective reagent in the oxidation of 2,3-bis(hydroxymethyl)-1-phenylnaphthalenes with preferential attack on 2-hydroxymethyl to yield normal lactones as the major products (>65percent).
HIGHLY REGIOSELECTIVE LACTONE FORMATION CATALYZED BY RUTHENIUM COMPLEXES. AN APPLICATION TO SYNTHESIS OF ARYLNAPHTHALENE LIGNANS
Ishii, Youichi,Ikariya, Takao,Saburi, Masahiko,Yoshikawa, Sadao
, p. 365 - 368 (2007/10/02)
Ruthenium catalyzed hydrogenation of cyclic anhydrides and dehydrogenation of diols have been successfully applied to the highly regioselective synthesis of arylnaphthalene lignans.
