New potential inhibitors of DNA topoisomerase. Part II: Design and synthesis of alpha-lapachone derivatives under microwave irradiation.

Abstract:

:A new series of potential inhibitors of DNA topoisomerase II were synthesized from facile materials (aromatic aldehydes, Meldrum's acid and 2-hydroxynaphthalene-1,4-dione) under microwave irradiation. The method provides a valuable tool in designing new and more potent cytotoxic analogues. This procedure is advantageous both economically and environmentally.

journal_name

Bioorg Med Chem Lett

authors

Wei P,Zhang X,Tu S,Yan S,Ying H,Ouyang P

doi

10.1016/j.bmcl.2008.12.006

subject

Has Abstract

pub_date

2009-02-01 00:00:00

pages

828-30

issue

3

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(08)01509-6

journal_volume

19

pub_type

杂志文章
  • Pharmacophore-based search, synthesis, and biological evaluation of anthranilic amides as novel blockers of the Kv1.5 channel.

    abstract::The search for novel, potent Kv1.5 blockers based on an anthranilic amide scaffold employing a pharmacophore-based virtual screening approach is described. The synthesis and structure-activity relationships (SAR) with respect to inhibition of the Kv1.5 channel are discussed. The most potent compounds display sub-micro...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.03.057

    authors: Peukert S,Brendel J,Pirard B,Strübing C,Kleemann HW,Böhme T,Hemmerle H

    更新日期:2004-06-07 00:00:00

  • Indole-based heterocyclic inhibitors of p38alpha MAP kinase: designing a conformationally restricted analogue.

    abstract::p38alpha Mitogen Activated Protein Kinase (MAP kinase) is an intracellular soluble serine threonine kinase. p38alpha kinase is activated in response to cellular stresses, growth factors and cytokines such as interleukin-1 (IL-1) and tumor necrosis factor alpha (TNF-alpha). The central role of p38alpha activation in se...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00653-x

    authors: Mavunkel BJ,Chakravarty S,Perumattam JJ,Luedtke GR,Liang X,Lim D,Xu YJ,Laney M,Liu DY,Schreiner GF,Lewicki JA,Dugar S

    更新日期:2003-09-15 00:00:00

  • Near-infrared fluorescent divalent RGD ligand for integrin αvβ₃-targeted optical imaging.

    abstract::A new near-infrared fluorescent compound containing two cyclic RGD motifs, cypate-[c(RGDfK)](2) (1), was synthesized based on a carbocyanine fluorophore bearing two carboxylic acid groups (cypate) for integrin α(v)β(3)-targeting. Compared with its monovalent counterpart cypate-c(RGDfK) (2), 1 exhibited remarkable impr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.07.044

    authors: Ye Y,Akers W,Xu B,Bloch S,Odonkor C,Achilefu S

    更新日期:2012-09-01 00:00:00

  • Design and synthesis of potent, orally-active DGAT-1 inhibitors containing a dioxino[2,3-d]pyrimidine core.

    abstract::A novel series of potent DGAT-1 inhibitors was developed originating from the lactam-based clinical candidate PF-04620110. Incorporation of a dioxino[2,3-d]pyrimidine-based core afforded good alignment of pharmacophore features and resulted in improved passive permeability. Development of an efficient, homochiral synt...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.08.028

    authors: Dow RL,Andrews M,Aspnes GE,Balan G,Michael Gibbs E,Guzman-Perez A,Karki K,Laperle JL,Li JC,Litchfield J,Munchhof MJ,Perreault C,Patel L

    更新日期:2011-10-15 00:00:00

  • Substituted tetrahydro-beta-carbolines as potential agents for the treatment of human papillomavirus infection.

    abstract::The identification and optimization of a series of substituted tetrahydro-beta-carbolines with potent activity against human papillomavirus is described. Structure-activity studies focused on the substitution pattern and chirality of the beta-carboline ring system are discussed. Optimization of these parameters led to...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.10.123

    authors: Miller JF,Turner EM,Sherrill RG,Gudmundsson K,Spaltenstein A,Sethna P,Brown KW,Harvey R,Romines KR,Golden P

    更新日期:2010-01-01 00:00:00

  • Synthesis and anti-angiogenesis activity of coumarin derivatives.

    abstract::A series of 7-diethylaminocoumarin compounds were synthesized and the cytotoxicities were tested against human umbilical vein endothelial cell (HUVEC) and some cancer cells. We found that the introduction of cyano groups at the 4-position will promote the bioactivity. In particular, compounds 9 and 10 strongly inhibit...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.06.007

    authors: Lee S,Sivakumar K,Shin WS,Xie F,Wang Q

    更新日期:2006-09-01 00:00:00

  • Design and synthesis of phosphotyrosine mimetics.

    abstract::Selective inhibitors of protein tyrosine phosphatases (PTPases) are of great interest as therapeutic agents and research tools. Several phenylalanine derivatives (1, 2) designed as phosphotyrosine mimetics or irreversible active site inhibitors were successfully synthesized, then incorporated into a combinatorial libr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00253-1

    authors: Yan Z,Kahn M,Qabar M,Urban J,Kim HO,Blaskovich MA

    更新日期:2003-06-16 00:00:00

  • 4,4-Disubstituted cyclohexylamine based CCR5 chemokine receptor antagonists as anti-HIV-1 agents.

    abstract::A series of 4,4-disubstituted cyclohexylamine based CCR5 antagonists has been designed and synthesized. Their antiviral structure-activity relationship has been extensively explored. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.07.074

    authors: Duan M,Aquino C,Dorsey GF Jr,Ferris R,Kazmierski WM

    更新日期:2009-09-01 00:00:00

  • Condensed E. coli cultures for highly efficient production of proteins containing unnatural amino acids.

    abstract::Current biosynthetic methods for producing proteins containing site-specifically incorporated unnatural amino acids are inefficient because the majority of the amino acid goes unused. Here we present a universal approach to improve the efficiency of such processes using condensed Escherichia coli cultures. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.08.049

    authors: Liu J,Castañeda CA,Wilkins BJ,Fushman D,Cropp TA

    更新日期:2010-10-01 00:00:00

  • Bicyclo((aryl)methyl)benzamides as inhibitors of GlyT1.

    abstract::A series of isoquinuclidine benzamides as glycine uptake inhibitors for the treatment of schizophrenia are described. Potency, lipophilicity, and intrinsic human microsomal clearance were parameters for optimization. Potency correlated with the nature of the ortho substituents of the benzamide ring, and reductions in ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.02.029

    authors: Varnes JG,Xiong H,Forst JM,Holmquist CR,Ernst GE,Frietze W,Dembofsky B,Andisik DW,Palmer WE,Hinkley L,Steelman GB,Wilkins DE,Tian G,Jonak G,Potts WM,Wang X,Brugel TA,Alhambra C,Wood MW,Veale CA,Albert JS

    更新日期:2018-04-01 00:00:00

  • Diphenyl ethers as androgen receptor antagonists for the topical suppression of sebum production.

    abstract::A series of diphenyl ethers was prepared and evaluated for androgen receptor antagonist activity in human androgen receptor binding and cellular functional assays. Analogs with potent in vitro activities were evaluated for topical in vivo efficacy in the Golden Syrian Hamster ear model. Several compounds showed reduct...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.02.104

    authors: Mitchell LH,Hu LY,Nguyen M,Fakhoury S,Smith Y,Iula D,Kostlan C,Carroll M,Dettling D,Du D,Pocalyko D,Wade K,Lefker B

    更新日期:2009-04-15 00:00:00

  • A new backbone of artificial enzymes obtained by cross-linkage of poly(ethylenimine).

    abstract::Cross-linkage of the branches of poly(ethylenimine) (PEI) suppresses flexibility of the polymer as revealed by decreased affinity of the amino groups on PEI backbone towards proton or Ni(II) ion. The cross-linkage improves ability of the PEI derivative equipped with beta-cyclodextrin to deacylate an ester containing t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00212-1

    authors: Suh J,Noh YS

    更新日期:1998-06-02 00:00:00

  • Structural characterization of P1'-diversified urea-based inhibitors of glutamate carboxypeptidase II.

    abstract::Urea-based inhibitors of human glutamate carboxypeptidase II (GCPII) have advanced into clinical trials for imaging metastatic prostate cancer. In parallel efforts, agents with increased lipophilicity have been designed and evaluated for targeting GCPII residing within the neuraxis. Here we report the structural and c...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.03.066

    authors: Pavlicek J,Ptacek J,Cerny J,Byun Y,Skultetyova L,Pomper MG,Lubkowski J,Barinka C

    更新日期:2014-05-15 00:00:00

  • Preparation of novel anthranilic acids as antibacterial agents: extensive evaluation of structural and physical properties on antibacterial activity and human serum albumin affinity.

    abstract::In the past few years a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected analogs ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.03.036

    authors: Thorarensen A,Li J,Wakefield BD,Romero DL,Marotti KR,Sweeney MT,Zurenko GE,Sarver RW

    更新日期:2007-06-01 00:00:00

  • Synthesis and evaluation of 5-HT(2A) and 5-HT(2C) receptor binding affinities of novel pyrimidine derivatives.

    abstract::In an effort to find potential anxiolytic and/or antipsychotic agents with selective 5-HT(2C) affinity a series of new pyrimidine derivatives was prepared and the binding affinities for 5-HT(2A) and 5-HT(2C) receptors were determined. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00660-1

    authors: Bózsing D,Simonek I,Simig G,Jakóczi I,Gacsályi I,Lévay G,Tihanyi K,Schmidt E

    更新日期:2002-11-04 00:00:00

  • Discovery of 3-aminopicolinamides as metabotropic glutamate receptor subtype 4 (mGlu4) positive allosteric modulator warheads engendering CNS exposure and in vivo efficacy.

    abstract::This letter describes the further chemical optimization of the picolinamide-derived family of mGlu4 PAMs wherein we identified a 3-amino substituent to the picolinamide warhead that engendered potency, CNS penetration and in vivo efficacy. From this optimization campaign, VU0477886 emerged as a potent (EC50=95nM, 89% ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.04.041

    authors: Gogliotti RD,Engers DW,Garcia-Barrantes PM,Panarese JD,Gentry PR,Blobaum AL,Morrison RD,Daniels JS,Thompson AD,Jones CK,Conn PJ,Niswender CM,Lindsley CW,Hopkins CR

    更新日期:2016-06-15 00:00:00

  • Synthesis and in vivo antihyperglycemic activity of 5-(1H-pyrazol-3-yl)methyl-1H-tetrazoles.

    abstract::A series of 5-[(5-aryl-1H-pyrazol-3-yl)methyl]-1H-tetrazoles 3a-h have been synthesized and evaluated for their in vivo antihyperglycemic activity. Some of the synthesized compounds have shown significant glucose lowering activity in male Sprague-Dawley rats in sucrose loaded model. These compounds were also evaluated...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.02.060

    authors: Sharon A,Pratap R,Tiwari P,Srivastava A,Maulik PR,Ram VJ

    更新日期:2005-04-15 00:00:00

  • A tetradecapeptide somatostatin dicarba-analog: Synthesis, structural impact and biological activity.

    abstract::We described here the first tetradecapeptide somatostatin-analogue where the disulfide bridge has been replaced by a carbon-carbon double bond. This analogue was prepared using microwave assisted ring closing metathesis (RCM) using the 2nd generation Grubbs as catalyst. Under our optimized conditions the cyclization b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.11.065

    authors: Martín-Gago P,Ramón R,Aragón E,Fernández-Carneado J,Martin-Malpartida P,Verdaguer X,López-Ruiz P,Colás B,Cortes MA,Ponsati B,Macias MJ,Riera A

    更新日期:2014-01-01 00:00:00

  • Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives.

    abstract::Ionic liquid ethyl ammonium nitrate is used as an excellent catalyst and solvent for three-component one-pot reaction of an aldehydes, amines and diethylphosphite to form novel α-aminophosphonates at room temperature. Among the various catalysts, the preparation of ethyl ammonium nitrate is an environmental friendly, ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.02.039

    authors: Dake SA,Raut DS,Kharat KR,Mhaske RS,Deshmukh SU,Pawar RP

    更新日期:2011-04-15 00:00:00

  • Carbonic anhydrase activators: the first X-ray crystallographic study of an adduct of isoform I.

    abstract::The X-ray crystallographic structure for the adduct of an activator with human carbonic anhydrase isozyme I (hCA I) is reported. L-Histidine binds deep within the enzyme active site, participating in a network of hydrogen bonds involving its carboxylate moiety and the zinc-bound water molecule, as well as the imidazol...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.07.021

    authors: Temperini C,Scozzafava A,Supuran CT

    更新日期:2006-10-01 00:00:00

  • Synthesis, antiproliferative and antibacterial activity of new amides of salinomycin.

    abstract::A series of 11 novel amides of salinomycin were synthesized for the first time. All the obtained compounds were found to show potent antiproliferative activity against human cancer cell lines including the drug-resistant cancer cells. Four new salinomycin derivatives revealed good antibacterial activity against clinic...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.02.042

    authors: Antoszczak M,Maj E,Stefańska J,Wietrzyk J,Janczak J,Brzezinski B,Huczyński A

    更新日期:2014-04-01 00:00:00

  • Synthesis of 2'-O-(N-methylcarbamoylethyl) 5-methyl-2-thiouridine and its application to splice-switching oligonucleotides.

    abstract::The effect of 2'-O-(N-methylcarbamoyl)ethyl (MCE) modification on splice-switching oligonucleotides (SSO) was systematically evaluated. The incorporation of five MCE nucleotides at the 5'-termini of SSOs effectively improved the splice switching effect. In addition, the incorporation of 2'-O-(N-methylcarbamoylethyl)-5...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.12.005

    authors: Masaki Y,Yamamoto K,Inde T,Yoshida K,Maruyama A,Nagata T,Tanihata J,Takeda S,Sekine M,Seio K

    更新日期:2019-01-15 00:00:00

  • Synthesis and evaluation of thiophenyl derivatives as inhibitors of alkaline phosphatase.

    abstract::Pathological calcifications induced by deposition of basic phosphate crystals or hydroxyapatite (HA) on soft tissues are a large family of diseases comprising of ankylosing spondylitis (AS), end-stage osteoarthritis (OA) and vascular calcification. High activity of tissue non-specific alkaline phosphatase (TNAP) is a ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.02.089

    authors: Chang L,Duy do L,Mébarek S,Popowycz F,Pellet-Rostaing S,Lemaire M,Buchet R

    更新日期:2011-04-15 00:00:00

  • Zwitterionic uracil derivatives as potent GnRH receptor antagonists with improved pharmaceutical properties.

    abstract::A novel series of potent zwitterionic uracil GnRH antagonists were discovered that showed reduced liability for CYP3A4 enzyme inhibition. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.07.059

    authors: Regan CF,Guo Z,Chen Y,Huang CQ,Chen M,Jiang W,Rueter JK,Coon T,Chen C,Saunders J,Brown MS,Betz SF,Struthers RS,Yang C,Wen J,Madan A,Zhu YF

    更新日期:2008-08-15 00:00:00

  • Identification of synthetic compounds active against VRE: the role of the lipidated aminoglucose and the structure of glycopeptide binding pocket.

    abstract::A modified vancomycin binding pocket (D-O-E ring) incorporating an alpha-hydroxy-beta-amino acid at the AA4 position is designed and synthesized. Some of these compounds display potent bioactivities against both sensitive- and resistant-strains (8 microg/ml against VREF). Both the lipidated aminoglucose and the struct...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.06.098

    authors: Jia Y,Gonzalez-Zamora E,Ma N,Liu Z,Bois-Choussy M,Malabarba A,Brunati C,Zhu J

    更新日期:2005-10-15 00:00:00

  • Azabicyclic sulfonamides as potent 11beta-HSD1 inhibitors.

    abstract::Inhibition of 11beta-HSD1 has demonstrated potential in the treatment of various components of metabolic syndrome. We wish to report herein the discovery of novel azabicyclic sulfonamide based 11beta-HSD1 inhibitors. Highly potent compounds exhibiting inhibitory activities at both human and mouse 11beta-HSD1 were iden...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.01.082

    authors: Shah U,Boyle CD,Chackalamannil S,Baker H,Kowalski T,Lee J,Terracina G,Zhang L

    更新日期:2010-03-01 00:00:00

  • Benzimidazole derivatives protect against cytokine-induced apoptosis in pancreatic β-Cells.

    abstract::Apoptotic cell death is the cause of the loss of insulin-producing β-cells in all forms of diabetes mellitus. The identification of small molecules capable of protecting cytokine-induced apoptosis could form the basis of useful therapeutic interventions. Here in, we present the discovery and synthesis of new benzimida...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.08.022

    authors: Zawawi NK,Rajput SA,Taha M,Ahmat N,Ismail NH,Abdullah N,Khan KM,Choudhary MI

    更新日期:2015-10-15 00:00:00

  • Synthesis of cynaropicrin-d(4).

    abstract::Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.10.065

    authors: Sato T,Hara S,Sato M,Ogawa K,Adams M,Usuki T

    更新日期:2015-12-01 00:00:00

  • Potent and selective CC-chemokine receptor-2 (CCR2) antagonists as a potential treatment for asthma.

    abstract::A number of compounds bearing a quaternary ammonium moiety were found to be antagonists with nanomolar binding affinity for the chemokine receptor-2. The structure-activity relationships in the series are described herein along with some detailed characterization of the interesting compounds. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.115

    authors: Lagu B,Gerchak C,Pan M,Hou C,Singer M,Malaviya R,Matheis M,Olini G,Cavender D,Wachter M

    更新日期:2007-08-01 00:00:00

  • Novel 1-alkynyl substituted 1,2-dihydroquinoline derivatives from nimesulide (and their 2-oxo analogues): a new strategy to identify inhibitors of PDE4B.

    abstract::A number of novel 1-(3-arylprop-2-ynyl) substituted 1,2-dihydroquinoline derivatives related to nimesulide and their 2-oxo analogues have been designed as potential inhibitors of PDE4. All these compounds were synthesized by using Sonogashira coupling as a key step. In vitro PDE4B inhibitory properties and molecular m...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.08.033

    authors: Pal S,Durgadas S,Nallapati SB,Mukkanti K,Kapavarapu R,Meda CL,Parsa KV,Pal M

    更新日期:2011-11-01 00:00:00