Molecular design, chemical synthesis, and biological evaluation of '4-1' pentacyclic aryl/heteroaryl-imidazonaphthalimides.


:A novel series of '4-1' pentacyclic naphthalimides, where the chromophore consists of a naphthalimide moiety, fused to an imidazole ring containing an unfused aryl or heteroaryl ring, were synthesized and evaluated for in vitro antitumor activity. In general, the new derivatives showed an improved cytotoxic activity over amonafide. DNA binding experiments supported that this class of compounds behaves as effective DNA-intercalating agents.


Bioorg Med Chem


Li F,Cui J,Guo L,Qian X,Ren W,Wang K,Liu F




Has Abstract


2007-08-01 00:00:00














  • Synthesis and evaluation of [14C]-labelled and fluorescent-tagged paclitaxel derivatives as new biological probes.

    abstract::Our present report deals with the preparation of hitherto unreported 7-([carbonyl-14C]-acetyl)paclitaxel 4 and two new bioactive 7-substituted fluorescent taxoids (FITC 9 and rhodamine 11), as well as evaluation towards their applications as biological probes. The results in this report demonstrate that (a) the new pa...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Rao CS,Chu JJ,Liu RS,Lai YK

    更新日期:1998-11-01 00:00:00

  • Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).

    abstract::High-throughput screening of a small-molecule library identified a 5-triazolo-2-arylpyridazinone as a novel inhibitor of the important glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3). Such inhibitors are of interest due to PFKFB3's control of the important glycolytic pathway used by cancer cel...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Brooke DG,van Dam EM,Watts CK,Khoury A,Dziadek MA,Brooks H,Graham LJ,Flanagan JU,Denny WA

    更新日期:2014-02-01 00:00:00

  • Synthesis and anti-HIV-1 evaluation of phosphonates which mimic the 5'-monophosphate of 4'-branched 2',3'-didehydro-2',3'-dideoxy nucleosides.

    abstract::Synthesis of the 4'-ethynyl and 4'-cyano phosphonates 8-11, which mimic the 5'-monophosphate of 4'-branched 2',3'-didehydro-2',3'-dideoxy nucleosides, was investigated by employing the 3',4'-unsaturated nucleosides (13 and 28) as the starting material. The synthesis was initiated by the electrophilic addition of NIS/(...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kubota Y,Ishizaki N,Haraguchi K,Hamasaki T,Baba M,Tanaka H

    更新日期:2010-10-15 00:00:00

  • The splicing modulator sulfonamide indisulam reduces AR-V7 in prostate cancer cells.

    abstract::Alternative splicing of the androgen receptor (AR) is frequently observed in castration resistant prostate cancer (CRPC). One AR isoform, the AR-V7 splice variant, is a constitutively active transcription factor which lacks a ligand binding domain and is therefore undruggable. AR-V7 expression correlates with resistan...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Melnyk JE,Steri V,Nguyen HG,Hann B,Feng FY,Shokat KM

    更新日期:2020-10-15 00:00:00

  • α-Glucosidase inhibition activity and in silico study of 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one, a synthetic derivative of flavone.

    abstract::A synthetic flavone derivative 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one (BDC) was synthesized by the one pot reaction method and assessed for α-glucosidase inhibitory activity. The BDC demonstrated dose dependent inhibition of α-glucosidase activity. A maximum inhibition (99.3 ± 0.26%) of α-glucosidase was observ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Meena SN,Kumar U,Naik MM,Ghadi SC,Tilve SG

    更新日期:2019-06-15 00:00:00

  • Targeting pancreatic cancer with a G-quadruplex ligand.

    abstract::The integrity of telomeres in most cancer cells is maintained by the action of the telomerase enzyme complex, which catalyzes the synthesis of telomeric DNA repeats in order to replace those lost during replication. Telomerase is especially up-regulated in metastatic cancer and is thus emerging as a major therapeutic ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gunaratnam M,de la Fuente M,Hampel SM,Todd AK,Reszka AP,Schätzlein A,Neidle S

    更新日期:2011-12-01 00:00:00

  • Solid phase synthesis and antiprotozoal evaluation of di- and trisubstituted 5'-carboxamidoadenosine analogues.

    abstract::The rapid increase of resistance to drugs commonly used in the treatment of tropical diseases such as malaria and African sleeping sickness calls for the prompt development of new safe and efficacious drugs. The pathogenic protozoan parasites lack the capability of synthesising purines de novo and they take up preform...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Rodenko B,Detz RJ,Pinas VA,Lambertucci C,Brun R,Wanner MJ,Koomen GJ

    更新日期:2006-03-01 00:00:00

  • CC-1065 CBI analogs: an example of enhancement of DNA alkylation efficiency through introduction of stabilizing electrostatic interactions.

    abstract::The three trimethylammonium salts 3-5 proved to be 100 times more efficient at alkylating DNA than 2 and exhibited DNA alkylation efficiencies identical to that of (+)-CC-1065 (1). In addition, the agents 3 and 4 exhibited DNA alkylation selectivities identical to that of 2. This may be attributed to spatially well-de...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Boger DL,Yun W,Han N,Johnson DS

    更新日期:1995-06-01 00:00:00

  • Synthesis and evaluation of a series of 1,4-diarylbutadienes for anticoccidial activity.

    abstract::During the course of a collaborative screening program, a set of 1-phenyl-4-pyridyl-butadienes was found to exhibit in vitro activity against Eimeria tenella in a cell-based assay. Activity was dependent on the chain length and degree of unsaturation of the linker between the two aryl groups as well as substitution of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gage JL,Kirst HA,O'Neil D,David BA,Smith CK 2nd,Naylor SA

    更新日期:2003-09-01 00:00:00

  • Palladium(II) saccharinate complexes with bis(2-pyridylmethyl)amine induce cell death by apoptosis in human breast cancer cells in vitro.

    abstract::The outcomes of breast cancer patients are still poor although new compounds have recently been introduced into the clinic. Therefore, novel chemical approaches are required. In the present study, palladium(II) and corresponding platinum(II) complexes containing bis(2-pyridylmethyl)amine (bpma) and saccharine were syn...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ari F,Ulukaya E,Sarimahmut M,Yilmaz VT

    更新日期:2013-06-01 00:00:00

  • Design, synthesis and biological evaluation of novel 4-phenoxy-6,7-disubstituted quinolines possessing (thio)semicarbazones as c-Met kinase inhibitors.

    abstract::In continuing our efforts to identify small molecules able to inhibit c-Met kinase, three series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives (23a-w, 26a-d and 30a-d) bearing (thio)semicarbazone scaffold were designed, synthesized and evaluated for their cytotoxicity. The biological data revealed that mos...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zhai X,Bao G,Wang L,Cheng M,Zhao M,Zhao S,Zhou H,Gong P

    更新日期:2016-03-15 00:00:00

  • Synthesis and preliminary cytotoxicity study of glucuronide derivatives of CC-1065 analogues.

    abstract::Glucuronide derivatives of CBI-bearing CC-1065 analogues have been synthesized, and their cytotoxicities tested against U937 leukemia cells. The new compounds show potent antitumor activity in vitro. Compounds 1 and 2, and their corresponding glucuronides 3 and 4 have IC(50) values of 0.6, 0.1, 1.4 and 0.6 nM, respect...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wang Y,Yuan H,Wright SC,Wang H,Larrick JW

    更新日期:2003-04-03 00:00:00

  • Design, synthesis, antiviral and cytostatic activity of ω-(1H-1,2,3-triazol-1-yl)(polyhydroxy)alkylphosphonates as acyclic nucleotide analogues.

    abstract::The efficient synthesis of a new series of polyhydroxylated dibenzyl ω-(1H-1,2,3-triazol-1-yl)alkylphosphonates as acyclic nucleotide analogues is described starting from dibenzyl ω-azido(polyhydroxy)alkylphosphonates and selected alkynes under microwave irradiation. Selected O,O-dibenzylphosphonate acyclonucleotides ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Głowacka IE,Balzarini J,Andrei G,Snoeck R,Schols D,Piotrowska DG

    更新日期:2014-07-15 00:00:00

  • Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives.

    abstract::3-Aryl-4-formylsydnone 4'-phenylthiosemicarbazones (3a-d) and 3-aryl-4-formylsydnone thiosemicarbazones (3e-h), which are precursors of 3-aryl-4-heterocyclic sydnones, are prepared by the condensation of 3-aryl-4-formylsydnones (1a-d) with 4'-phenylthiosemicarbazide (2a) and thiosemicarbazide (2b), respectively. The t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Shih MH,Ke FY

    更新日期:2004-09-01 00:00:00

  • Synthesis and evaluation of 18F labeled crizotinib derivative [18F]FPC as a novel PET probe for imaging c-MET-positive NSCLC tumor.

    abstract::c-MET-positive NSCLC is an important subtype accounting for about 5%~22% of lung cancer. NSCLC patients with activating c-MET are intensively sensitive to c-MET selective receptor tyrosine kinase (RTK) inhibitors, so we aimed to develop a specific PET probe targeting to c-MET-positive NSCLC for potential patients scre...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lin Q,Zhang Y,Fu Z,Hu B,Si Z,Zhao Y,Shi H,Cheng D

    更新日期:2020-08-01 00:00:00

  • A novel sesquiterpene lactone from Centaurea pullata: structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties.

    abstract::A novel elemanolide with an alpha-methyl-gamma-lactone moiety, 8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)melitensine, in addition to four known sesquiterpene lactones also bearing the same lactone ring, melitensin, 11beta,13 dihydrosalonitenolide, 8alpha-hydroxy-11beta,13-dihydro-4-epi-sonchucarpolide, and 8alpha-hyd...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Djeddi S,Karioti A,Sokovic M,Koukoulitsa C,Skaltsa H

    更新日期:2008-04-01 00:00:00

  • Adenosine receptors: new opportunities for future drugs.

    abstract::This review summarises current knowledge on adenosine receptors, an important G protein-coupled receptor. The four known adenosine receptor subtypes A1, A2A, A2B, and A3 are discussed with special reference to the opportunities for drug development. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Poulsen SA,Quinn RJ

    更新日期:1998-06-01 00:00:00

  • The square conformation of phenylglycine-incorporated ascidiacyclamide is stabilized by CH/π interactions between amino acid side chains.

    abstract::We designed a phenylglycine (Phg)-incorporated ascidiacyclamide (ASC) analogue, cyclo(-Phg-oxazoline-d-Val-thiazole-Ile-oxazoline-d-Val-thiazole- ([Phg]ASC), with the aim of stabilizing the square conformation of ASC through interactions between amino acid side chains. X-ray diffraction analysis showed that [Phg]ASC h...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Asano A,Yamada T,Doi M

    更新日期:2011-06-01 00:00:00

  • Anti-HBV and cytotoxic activities of pyranocoumarin derivatives.

    abstract::Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human ca...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Su CR,Yeh SF,Liu CM,Damu AG,Kuo TH,Chiang PC,Bastow KF,Lee KH,Wu TS

    更新日期:2009-08-15 00:00:00

  • Structural advantage of dendritic poly(L-lysine) for gene delivery into cells.

    abstract::This study aimed to investigate the relationships between structures of gene carrier molecules and their activities for gene delivery into cells. We compared 2 types of poly(L-lysine) as carriers, that is, dendritic poly(L-lysine) (KG6) and linear poly(L-lysine) (PLL). KG6 formed a neutral DNA complex, and its DNA com...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yamagata M,Kawano T,Shiba K,Mori T,Katayama Y,Niidome T

    更新日期:2007-01-01 00:00:00

  • Synthesis and testing of azaglutamine derivatives as inhibitors of hepatitis A virus (HAV) 3C proteinase.

    abstract::Hepatitis A virus (HAV) 3C proteinase is a picornaviral cysteine proteinase that is essential for cleavage of the initially synthesized viral polyprotein precursor to mature fragments and is therefore required for viral replication in vivo. Since the enzyme generally recognizes peptide substrates with L-glutamine at t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Huang Y,Malcolm BA,Vederas JC

    更新日期:1999-04-01 00:00:00

  • Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials.

    abstract::Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Xiao ZP,He XB,Peng ZY,Xiong TJ,Peng J,Chen LH,Zhu HL

    更新日期:2011-03-01 00:00:00

  • Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol.

    abstract::Using 3β-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Saini R,Kataeva O,Schmidt AW,Wang Y,Meljon A,Griffiths WJ,Knölker HJ

    更新日期:2013-09-15 00:00:00

  • 3D-chiral quadratic indices of the 'molecular pseudograph's atom adjacency matrix' and their application to central chirality codification: classification of ACE inhibitors and prediction of sigma-receptor antagonist activities.

    abstract::Quadratic indices of the 'molecular pseudograph's atom adjacency matrix' have been generalized to codify chemical structure information for chiral drugs. These 3D-chiral quadratic indices make use of a trigonometric 3D-chirality correction factor. These indices are nonsymmetric and reduced to classical (2D) descriptor...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ponce YM,Diaz HG,Zaldivar VR,Torrens F,Castro EA

    更新日期:2004-10-15 00:00:00

  • Probing linker design in citric acid-ciprofloxacin conjugates.

    abstract::A series of structurally related citric acid-ciprofloxacin conjugates was synthesised to investigate the influence of the linker between citric acid and ciprofloxacin on antibacterial activities. Minimum inhibitory concentrations (MICs) were determined against a panel of reference strains and clinical isolates of bact...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Milner SJ,Snelling AM,Kerr KG,Abd-El-Aziz A,Thomas GH,Hubbard RE,Routledge A,Duhme-Klair AK

    更新日期:2014-08-15 00:00:00

  • New acridone-4-carboxylic acid derivatives as potential inhibitors of hepatitis C virus infection.

    abstract::A new class of compounds--acridone derivatives--was tested using the direct fluorometric helicase activity assay to determine the inhibitory properties of the derivatives towards the NS3 helicase of Hepatitis C virus (HCV). The compounds were also tested as putative transcription inhibitors of in vitro transcription b...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Stankiewicz-Drogon A,Palchykovska LG,Kostina VG,Alexeeva IV,Shved AD,Boguszewska-Chachulska AM

    更新日期:2008-10-01 00:00:00

  • Induction of potent cell growth inhibition by schizophyllan/K-ras antisense complex in combination with gemcitabine.

    abstract::Antisense oligonucleotides (AS-ODNs) specifically hybridize with target mRNAs, resulting in interference with the splicing mechanism or the regulation of protein translation. In our previous reports, we demonstrated that β-glucan schizophyllan (SPG) can form a complex with AS-ODNs attached with oligo deoxyadenosine dA...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sasaki S,Izumi H,Morimoto Y,Sakurai K,Mochizuki S

    更新日期:2020-09-15 00:00:00

  • Synthesis and biological evaluation of irreversible EGFR tyrosine kinase inhibitors containing pyrido[3,4-d]pyrimidine scaffold.

    abstract::In the present study, a new class of compounds containing pyrido[3,4-d]pyrimidine scaffold with an acrylamide moiety was designed as irreversible EGFR-TKIs to overcome acquired EGFR-T790M resistance. The most promising compound 25h inhibited HCC827 and H1975 cells growth with the IC50 values of 0.025 μM and 0.49 μM, r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zhang H,Wang J,Zhao HY,Yang XY,Lei H,Xin M,Cao YX,Zhang SQ

    更新日期:2018-07-23 00:00:00

  • Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: toward a structure/activity correlation.

    abstract::On the grounds of previous encouraging results on the antitumor activity of (1E,3E)-1,4-bis(1-naphthyl)-2,3-dinitro-1,3-butadiene (1), we have designed and synthesized two new molecules [(1E,3E)-1,4-bis(4-carboxy-1-naphthyl)-2,3-dinitro-1,3-butadiene (2) and methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Petrillo G,Mariggiò MA,Aiello C,Cordazzo C,Fenoglio C,Morganti S,Croce M,Rizzato E,Spinelli D,Maccagno M,Bianchi L,Prevosto C,Tavani C,Viale M

    更新日期:2008-01-01 00:00:00

  • Hippuryl-alpha-methylphenylalanine and hippuryl-alpha-methylphenyllactic acid as substrates for carboxypeptidase A. Syntheses, kinetic evaluation and mechanistic implication.

    abstract::(R)- and (S)-Hippuryl-alpha-methylphenylalanine [(R)- and (S)-Hipp-alpha-MePhe] and (S)-hippuryl-alpha-methylphenyllactic acid [(S)-Hipp-alpha-MeOPhe] were synthesized and evaluated as substrates for carboxypeptidase A (CPA) in an effort to shed further light on the catalytic mechanism of the enzyme. The rate of CPA-c...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lee M,Kim DH

    更新日期:2000-04-01 00:00:00