Arylnaphthalene lactone analogues: synthesis and development as excellent biological candidates for future drug discovery

Arylnaphthalene lactones are natural products extracted from a wide range of different parts of plants. The progressing interest in the synthesis of these compounds is due to their significant biological activities, which have made them potential candidates in drug discovery and development. This review mainly covers recent developments in the synthesis and biological applications of arylnaphthalene lactone analogs.

[1]  Lijun Rong,et al.  Potent Inhibitor of Drug-Resistant HIV-1 Strains Identified from the Medicinal Plant Justicia gendarussa. , 2017, Journal of natural products.

[2]  D. Mal,et al.  Transpositive Tandem Annulation of Phthalides with Allene Carboxylates: Regioselective Synthesis of Arylnaphthalene Lignans. , 2016, The Journal of organic chemistry.

[3]  Dongyun Shin,et al.  Synthesis of arylnaphthalene lignan lactone using benzoin condensation, intramolecular thermal cyclization and Suzuki coupling , 2015 .

[4]  P. Forgó,et al.  Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain. , 2014, Journal of natural products.

[5]  L. Kocsis,et al.  Intramolecular Dehydro-Diels–Alder Reaction Affords Selective Entry to Arylnaphthalene or Aryldihydronaphthalene Lignans , 2014, Organic letters.

[6]  A. Kinghorn,et al.  Potent Cytotoxic Arylnaphthalene Lignan Lactones from Phyllanthus poilanei , 2014, Journal of natural products.

[7]  Xuesen Fan,et al.  Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles. , 2014, Chemical communications.

[8]  W. Kong,et al.  Evaluation and Structure-Activity Relationship Analysis of a New Series of Arylnaphthalene lignans as Potential Anti-Tumor Agents , 2014, PloS one.

[9]  Seung‐Yong Seo,et al.  Regioselective route for arylnaphthalene lactones: convenient synthesis of taiwanin C, justicidin E, and daurinol , 2014 .

[10]  Rui Ge,et al.  Catalyst-free intramolecular formal carbon insertion into σ-C-C bonds: a new approach toward phenanthrols and naphthols. , 2013, Angewandte Chemie.

[11]  M. Heravi,et al.  Recent Applications of the Suzuki Reaction in Total Synthesis , 2012 .

[12]  Wei Zhang,et al.  Design, synthesis and biological evaluation of novel glycosylated diphyllin derivatives as topoisomerase II inhibitors. , 2012, European journal of medicinal chemistry.

[13]  Jie Hui,et al.  Synthesis and in vitro anticancer activities of novel aryl-naphthalene lignans , 2011, Medicinal Chemistry Research.

[14]  R. Balamurugan,et al.  Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation. , 2011, The Journal of organic chemistry.

[15]  A. Mohagheghzadeh,et al.  Lignans in flowering aerial parts of Linum species--chemodiversity in the light of systematics and phylogeny. , 2010, Phytochemistry.

[16]  P. Anastas,et al.  Advances in the methodology of a multicomponent synthesis of arylnaphthalene lactones , 2010 .

[17]  P. Anastas,et al.  Silver-catalyzed one-pot synthesis of arylnaphthalene lactone natural products. , 2010, Journal of natural products.

[18]  S. Yeh,et al.  Synthesis and the Biological Evaluation of Arylnaphthalene Lignans as Anti‐hepatitis B Virus Agents , 2010, Bioorganic & medicinal chemistry.

[19]  Wang Dan,et al.  Synthesis and bioevaluation of novel analogues of justicidin A , 2010, Medicinal Chemistry Research.

[20]  Herbert Waldmann,et al.  Synthesis of natural product inspired compound collections. , 2009, Angewandte Chemie.

[21]  P. Arya,et al.  Advances in solution- and solid-phase synthesis toward the generation of natural product-like libraries. , 2009, Chemical reviews.

[22]  P. Anastas,et al.  Silver-catalyzed one-pot synthesis of arylnaphthalene lactones. , 2008, The Journal of organic chemistry.

[23]  T. Schmidt,et al.  (+)‐Pinoresinol/(−)‐lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B , 2007, FEBS letters.

[24]  D. Newman,et al.  Natural products as sources of new drugs over the last 25 years. , 2007, Journal of natural products.

[25]  Shwu-Jen Wu,et al.  Cytotoxic arylnaphthalene lignans from Phyllanthus oligospermus. , 2006, Chemical & pharmaceutical bulletin.

[26]  Y. Li,et al.  Inhibition of Hepatitis B Virus Gene Expression and Replication by Helioxanthin and its Derivative , 2005, Antiviral chemistry & chemotherapy.

[27]  E. Yoshida,et al.  Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of unsymmetrically substituted alpha-arylnaphthalenes: application to total synthesis of natural lignan lactones. , 2005, The Journal of organic chemistry.

[28]  E. Huang,et al.  Synthesis and antiviral activity of helioxanthin analogues. , 2005, Journal of medicinal chemistry.

[29]  Shoei‐Sheng Lee,et al.  Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans. , 2004, Bioorganic & medicinal chemistry.

[30]  M. Mori,et al.  Arylnaphthalene lignans through Pd-Catalyzed [2+2+2] cocyclization of arynes and diynes: total synthesis of Taiwanins C and E. , 2004, Angewandte Chemie.

[31]  Chun-nan Lin,et al.  Two New Arylnaphthalide Lignans and Antiplatelet Constituents from Justicia procumbens , 2004, Archiv der Pharmazie.

[32]  Chun-chung Lee,et al.  A Novel Topoisomerase II Poison GL331 Preferentially Induces DNA Cleavage at (C/G)T Sites and Can Cause Telomere DNA Damage , 2001, Pharmaceutical Research.

[33]  J. Whang‐Peng,et al.  In vitro evaluation of GL331's cancer cell killing and apoptosis-inducing activity in combination with other chemotherapeutic agents , 2000, Apoptosis.

[34]  W. Berdel,et al.  Phase I clinical and pharmacokinetic trial of the podophyllotoxin derivative NK611 administered as intravenous short infusion , 1998, Investigational New Drugs.

[35]  S. Apers,et al.  Lignans and neolignans as lead compounds , 2004, Phytochemistry Reviews.

[36]  C. Yuan,et al.  A Novel Podophyllotoxin-Derived Compound GL331 Is More Potent than Its Congener VP-16 in Killing Refractory Cancer Cells , 2004, Pharmaceutical Research.

[37]  B. Das,et al.  Arylnaphthalide lignans from Cleistanthus collinus. , 2003, Chemical & pharmaceutical bulletin.

[38]  B. Hill,et al.  F 11782, a novel catalytic inhibitor of topoisomerases I and II, induces atypical, yet cytotoxic DNA double-strand breaks in CHO-K1 cells. , 2002, Anticancer research.

[39]  A. Arai,et al.  The carboxyl terminus of the prolactin-releasing peptide receptor interacts with PDZ domain proteins involved in alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptor clustering. , 2001, Molecular pharmacology.

[40]  H. Huang,et al.  GL331 induces down-regulation of cyclin D1 expression via enhanced proteolysis and repressed transcription. , 2001, Molecular pharmacology.

[41]  K. Kawazoe,et al.  Phenylnaphthalene compounds from the subterranean part of Vitex rotundifolia and their antibacterial activity against methicillin-resistant Staphylococcus aureus. , 2001, Journal of natural products.

[42]  P. Renard,et al.  Antitumor agents. Synthesis and biological evaluation of new compounds related to podophyllotoxin, containing the 2,3-dihydro-1,4-benzodioxin system. , 2001, European journal of medicinal chemistry.

[43]  J. Charlton,et al.  Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans , 2000 .

[44]  S. Yamazaki Chromium(VI) Oxide-Catalyzed Benzylic Oxidation with Periodic Acid , 1999 .

[45]  J. Kotera,et al.  1-Arylnaphthalene lignan: a novel scaffold for type 5 phosphodiesterase inhibitor. , 1999, Journal of medicinal chemistry.

[46]  K. Lee,et al.  A high yield preparation of 2-fluoropodophyllotoxin☆ , 1999 .

[47]  B. Hill,et al.  Synthesis and antitumor activity of new glycosides of epipodophyllotoxin, analogues of etoposide, and NK 611. , 1998, Journal of medicinal chemistry.

[48]  C. Monneret,et al.  A one-pot, efficient synthesis of the potent cytotoxic podophyllotoxin derivative NPF , 1997 .

[49]  C. Teng,et al.  Antiplatelet arylnaphthalide lignans from Justicia procumbens , 1996 .

[50]  J. Falgueyret,et al.  Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: structure-activity relationship study directed toward the improvement of metabolic stability. , 1996, Journal of medicinal chemistry.

[51]  O. Kaminuma,et al.  Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene lignans. , 1996, Journal of medicinal chemistry.

[52]  T. Tsuruo,et al.  Antitumor activity of a novel podophyllotoxin derivative (TOP-53) against lung cancer and lung metastatic cancer. , 1996, Cancer research.

[53]  C. L. Liu,et al.  Six lignans from Phyllanthus myrtifolius. , 1996, Journal of natural products.

[54]  J. Lin,et al.  Differential inhibition of reverse transcriptase and cellular DNA polymerase-alpha activities by lignans isolated from Chinese herbs, Phyllanthus myrtifolius Moon, and tannins from Lonicera japonica Thunb and Castanopsis hystrix. , 1995, Antiviral research.

[55]  J. Falgueyret,et al.  Naphthalenic lignan lactones as selective, nonredox 5-lipoxygenase inhibitors. Synthesis and biological activity of (methoxyalkyl)thiazole and methoxytetrahydropyran hybrids. , 1994, Journal of medicinal chemistry.

[56]  R. Ward Lignans, neolignans, and related compounds. , 1995, Natural product reports.

[57]  J. Falgueyret,et al.  Justicidin E: A new leukotriene biosynthesis inhibitor. , 1993 .

[58]  H. Ohmizu,et al.  A New Synthesis of Arylnaphthalene Lignan Lactones , 1992 .

[59]  P. Anastas,et al.  Synthesis of Natural Lignan Arylnaphthalene Lactones, Daurinol and Retrochinensin , 1991 .

[60]  R. Stevenson,et al.  Synthesis of lignan aryldihydronaphthalene lactones by cyclization of cinnamyl arylpropiolate esters: revised structure of beta-apopolygamatin. , 1991, Journal of natural products.

[61]  R. Stevenson,et al.  Improved Methods of Synthesis of Lignan Arylnaphthalene Lactones via Arylpropargyl Arylpropiolate Esters , 1989 .

[62]  R. Ward,et al.  Synthesis of lignan lactones by conjugate addition of thioacetal carbanions to butenolide , 1983 .

[63]  R. Ahmed,et al.  Hydroxymethylphenylnaphthoie acid lactones , 1974 .

[64]  J. R. Cole,et al.  Antitumor activity of Bursera schlechtendalii (burseraceae): isolation and structure determination of two new lignans. , 1972, Journal of pharmaceutical sciences.