N-Aroyl-3,5-bis(benzylidene)-4-piperidones: a novel class of antimycobacterial agents.


:A number of 3,5-bis(benzylidene)-4-piperidones 1 and some N-4-(2-aminoethoxy)phenylcarbonyl analogs 3-6 display excellent in vitro antimycobacterial properties. In particular, 1c and 6d are potent antimycobacterials which are well tolerated in mice and are identified as important lead molecules. The nature of both the benzylidene aryl rings and the terminal basic groups which affect the antimycobacterial potencies and the absence of neurotoxic side effects were identified. Several representative compounds stimulated respiration in mitochondria isolated from rat liver and this effect was not caused by the swelling of these organelles. Various guidelines for the creation of further related novel antimycobacterial agents are provided.


Bioorg Med Chem


Das U,Das S,Bandy B,Stables JP,Dimmock JR




Has Abstract


2008-04-01 00:00:00














  • A new opioid designed multiple ligand derived from the micro opioid agonist endomorphin-2 and the delta opioid antagonist pharmacophore Dmt-Tic.

    abstract::Opioid compounds with mixed micro agonist/delta antagonist properties could be used as analgesics with low propensity to induce tolerance and dependence. Here we report the synthesis of a new designed multiple ligand deriving from the micro selective agonist endomorphin-2 and the delta selective antagonist pharmacopho...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Salvadori S,Trapella C,Fiorini S,Negri L,Lattanzi R,Bryant SD,Jinsmaa Y,Lazarus LH,Balboni G

    更新日期:2007-11-15 00:00:00

  • Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity.

    abstract::4-Aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and its analogues have been found to be compounds of interest for their anti-inflammatory, analgesic, antiviral, antipyretic, antirheumatic and antimicrobial activities. In the present study, Schiff base analogues of 4-aminoantipyrine were synthesized by ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Alam MS,Choi JH,Lee DU

    更新日期:2012-07-01 00:00:00

  • 3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.

    abstract::Following our studies on structure-activity relationships of anti-rhinovirus chromene and chroman derivatives, we designed and synthesized new series of 3-phenylalkyl-2H-chromenes and -chromans bearing differently sized, aliphatic linker chains between the two cycles. The cytotoxicity and the antiviral activity of the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Conti C,Proietti Monaco L,Desideri N

    更新日期:2017-04-01 00:00:00

  • Synthesis and studies of 3'-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base.

    abstract::3'-Deoxy-3'-C-CF3, 2',3'-dideoxy-3'-C-CF3 and 2',3'-unsaturated-3'-C-CF3 nucleoside derivatives of adenosine and cytidine have been synthesized. All these derivatives were prepared by glycosylation of adenine and uracil with a suitable peracylated 3-trifluoromethyl sugar precursor. The resulting protected nucleosides ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Jeannot F,Gosselin G,Standring D,Bryant M,Sommadossi JP,Giulia Loi A,La Colla P,Mathé C

    更新日期:2002-10-01 00:00:00

  • Synthesis of indomethacin analogues for evaluation as modulators of MRP activity.

    abstract::Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Maguire AR,Plunkett SJ,Papot S,Clynes M,O'Connor R,Touhey S

    更新日期:2001-03-01 00:00:00

  • Conversion of iodine to fluorine-18 based on iodinated chalcone and evaluation for β-amyloid PET imaging.

    abstract::In the amyloid cascade hypothesis, β-amyloid (Aβ) plaques is one of the major pathological biomarkers in the Alzheimer's disease (AD) brain. We report the synthesis and evaluation of novel radiofluorinated chalcones, [18F]4-dimethylamino-4'-fluoro-chalcone ([18F]DMFC) and [18F]4'-fluoro-4-methylamino-chalcone ([18F]FM...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kaide S,Ono M,Watanabe H,Shimizu Y,Nakamoto Y,Togashi K,Yamaguchi A,Hanaoka H,Saji H

    更新日期:2018-07-23 00:00:00

  • Interaction between double helix DNA fragments and a new topopyrone acting as human topoisomerase I poison.

    abstract::A water soluble derivative (2) of topopyrones was selected for NMR studies directed to elucidate the mode of binding with specific oligonucleotides. Topopyrone 2 can intercalate into the CG base pairs, but the residence time into the double helix is very short and a fast chemical exchange averaging occurs at room temp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Scaglioni L,Mazzini S,Mondelli R,Dallavalle S,Gattinoni S,Tinelli S,Beretta GL,Zunino F,Ragg E

    更新日期:2009-01-15 00:00:00

  • Photo-control of nitric oxide synthase activity using a caged isoform specific inhibitor.

    abstract::Nitric oxide (NO) plays a critical role in a number of physiological processes and is produced in mammalian cells by nitric oxide synthase (NOS) isozymes. Because of the diverse functions of NO, pharmaceutical interventions which seek to abrogate adverse effects of excess NOS activity must not interfere with the norma...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Montgomery HJ,Perdicakis B,Fishlock D,Lajoie GA,Jervis E,Guy Guillemette J

    更新日期:2002-06-01 00:00:00

  • Synthesis and characterization of modified nucleotides in the 970 hairpin loop of Escherichia coli 16S ribosomal RNA.

    abstract::The synthesis of the 6-O-DPC-2-N-methylguanosine (m(2)G) nucleoside and the corresponding 5'-O-DMT-2'-O-TOM-protected 6-O-DPC-2-N-methylguanosine phosphoramidite is reported [DPC, diphenyl carbamoyl; DMT, 4,4'-dimethoxytrityl; TOM, [(triisopropylsilyl)oxy]methyl]. The availability of the phosphoramidite allows for syn...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Abeydeera ND,Chow CS

    更新日期:2009-08-15 00:00:00

  • Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site.

    abstract::A number of N-phenyl-N'-(2-chloroethyl)ureas (CEUs) have been shown to be potent antimitotics through their covalent binding to the colchicine-binding site on intracellular beta-tubulin. The present communication aimed to evaluate the role of the electrophilic 2-chloroethyl amino moiety of CEU on cell growth inhibitio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Fortin JS,Lacroix J,Desjardins M,Patenaude A,Petitclerc E,C-Gaudreault R

    更新日期:2007-07-01 00:00:00

  • Synthesis and dopamine receptor binding of sulfur-containing aporphines.

    abstract::We investigated acid-catalyzed rearrangement of thebaine 14 and its N-propyl analog 15 with methanesulfonic acid in the presence of the nucleophiles methanethiol and hydrogen sulfide. R(-)-2-methylthioapocodeine 16, R(-)-2-methylthioapomorphine 18, and their N-n-propyl analogs 17, 19 were obtained by rearrangement in ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tóth M,Berényi S,Csutorás C,Kula NS,Zhang K,Baldessarini RJ,Neumeyer JL

    更新日期:2006-03-15 00:00:00

  • Synthesis and anti-influenza virus activity of dihydrofuran-fused perhydrophenanthrenes with a benzyloxy-type side-chain.

    abstract::As one of our ongoing research project concerning development of a novel anti-influenza virus agent, dihydrofuran-fused perhydrophenanthrenes were derivatized by means of Williamson ether synthesis and Suzuki-Miyaura cross coupling reactions. Newly synthesized compounds were subjected to evaluation of anti-influenza v...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Matsuya Y,Suzuki N,Kobayashi SY,Miyahara T,Ochiai H,Nemoto H

    更新日期:2010-02-15 00:00:00

  • Synergistic reduction of HIV-1 infectivity by 5-azacytidine and inhibitors of ribonucleotide reductase.

    abstract::Although many compounds have been approved for the treatment of human immunodeficiency type-1 (HIV-1) infection, additional anti-HIV-1 drugs (particularly those belonging to new drug classes) are still needed due to issues such as long-term drug-associated toxicities, transmission of drug-resistant variants, and devel...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Rawson JM,Roth ME,Xie J,Daly MB,Clouser CL,Landman SR,Reilly CS,Bonnac L,Kim B,Patterson SE,Mansky LM

    更新日期:2016-06-01 00:00:00

  • Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ko H,Carter RL,Cosyn L,Petrelli R,de Castro S,Besada P,Zhou Y,Cappellacci L,Franchetti P,Grifantini M,Van Calenbergh S,Harden TK,Jacobson KA

    更新日期:2008-06-15 00:00:00

  • Dolichylpyrophosphate oligosaccharides: large-scale isolation and evaluation as oligosaccharyltransferase substrates.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gibbs BS,Coward JK

    更新日期:1999-03-01 00:00:00

  • DNA sequence-specific recognition of peptides incorporating the HPRK and polyamide motifs.

    abstract::Three peptide amides, HPRK(Py)(4)HPRK-NH(2) (PyH-12), HPRK(Py)(3)HPRK-NH(2) (PyH-11) and HPRK(Py)(2)HPRK-NH(2) (PyH-10), incorporating two HPRK motifs and various 4-amino-1-methylpyrrole-2-carboxylic acid residues (Py) were synthesized by solid-phase peptide methodology. The binding of these three peptides to a 5'-32P...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chang JC,Yang CH,Chou PY,Yang WH,Chou IC,Lu CT,Lin PH,Hou RC,Jeng KC,Cheng CC,Sheh L

    更新日期:2004-01-02 00:00:00

  • Evaluation of histone deacetylase inhibitors (HDACi) as therapeutic leads for human African trypanosomiasis (HAT).

    abstract::Two of the histone deacetylases, TbDAC1 and TbDAC3, have been reported to be essential genes in trypanosomes. Therefore, we tested the activity of a panel of human histone deacetylase inhibitors (HDACi) for their ability to block proliferation of Trypanosoma brucei brucei. Among the HDACi's, the hydroxamic acid deriva...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Carrillo AK,Guiguemde WA,Guy RK

    更新日期:2015-08-15 00:00:00

  • Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents.

    abstract::KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we furt...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yamazaki Y,Sumikura M,Masuda Y,Hayashi Y,Yasui H,Kiso Y,Chinen T,Usui T,Yakushiji F,Potts B,Neuteboom S,Palladino M,Lloyd GK,Hayashi Y

    更新日期:2012-07-15 00:00:00

  • Decades-old renin inhibitors are still struggling to find a niche in antihypertensive therapy. A fleeting look at the old and the promising new molecules.

    abstract::Hypertension is a diverse illness interlinked with cerebral, cardiovascular (CVS) and renal abnormalities. Presently, the malady is being treated by focusing on Renin- angiotensin system (RAS), voltage-gated calcium channels, peripheral vasodilators, renal and sympathetic nervous systems. Cardiovascular and renal abno...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ramya K,Suresh R,Kumar HY,Kumar BRP,Murthy NBS

    更新日期:2020-05-15 00:00:00

  • Design, synthesis and biological evaluation of N-phenylthieno[2,3-d]pyrimidin-4-amines as inhibitors of FGFR1.

    abstract::Fibroblast grow factor receptor 1 (FGFR1) is an important anti-cancer target that plays crucial role in oncogenesis and oncogenic angiogenesis. The structure-activity relationship (SAR) of N-phenylthieno[2,3-d]pyrimidin-4-amines was investigated. Binding of active compounds with FGFR1 kinase was analyzed by molecular ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gryshchenko AA,Bdzhola VG,Balanda AO,Briukhovetska NV,Kotey IM,Golub AG,Ruban TP,Lukash LL,Yarmoluk SM

    更新日期:2015-05-01 00:00:00

  • The tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold.

    abstract::Thirteen (Z)-4-(substituted benzylidene)-3-phenylisoxazol-5(4H)-ones were designed to confirm the geometric effect of the double bond of the β-phenyl-α, β-unsaturated carbonyl scaffold on tyrosinase inhibitory activity. Compounds 1a-1m, which all possessed the (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold, were synt...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kim SJ,Yang J,Lee S,Park C,Kang D,Akter J,Ullah S,Kim YJ,Chun P,Moon HR

    更新日期:2018-08-07 00:00:00

  • An efficient substitution reaction for the preparation of thyroid hormone analogues.

    abstract::The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yoshihara HA,Chiellini G,Mitchison TJ,Scanlan TS

    更新日期:1998-08-01 00:00:00

  • Interaction between artemisinin and heme. A Density Functional Theory study of structures and interaction energies.

    abstract::Malaria is an infectious disease caused by the unicellular parasite Plasmodium sp. Currently, the malaria parasite is becoming resistant to the traditional pharmacological alternatives, which are ineffective. Artemisinin is the most recent advance in the chemotherapy of malaria. Since it has been proven that artemisin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Araújo JQ,Carneiro JW,de Araujo MT,Leite FH,Taranto AG

    更新日期:2008-05-01 00:00:00

  • The role of molecular modeling in the design of analogues of the fungicidal natural products crocacins A and D.

    abstract::Extensive molecular modeling based on crystallographic data was used to aid the design of synthetic analogues of the fungicidal naturally occurring respiration inhibitors crocacins A and D, and an inhibitor binding model to the mammalian cytochrome bc(1) complex was constructed. Simplified analogues were made which sh...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Crowley PJ,Berry EA,Cromartie T,Daldal F,Godfrey CR,Lee DW,Phillips JE,Taylor A,Viner R

    更新日期:2008-12-15 00:00:00

  • Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis.

    abstract::Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacter...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Samala G,Brindha Devi P,Saxena S,Gunda S,Yogeeswari P,Sriram D

    更新日期:2016-11-01 00:00:00

  • Mechanism-based inhibitors of serine proteases with high selectivity through optimization of S' subsite binding.

    abstract::A series of mechanism-based inhibitors designed to interact with the S' subsites of serine proteases was synthesized and their inhibitory activity toward the closely-related serine proteases human neutrophil elastase (HNE) and proteinase 3 (PR 3) was investigated. The compounds were found to be time-dependent inhibito...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Li Y,Dou D,He G,Lushington GH,Groutas WC

    更新日期:2009-05-15 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 of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide.

    abstract::In order to increase metabolic stability and water solubility of arenastatin A, an extremely potent cytotoxic depsipeptide from the Okinawan marine sponge of Dysidea arenaria, several 15,20-triamide analogues with a polar substituent on the phenyl ring were synthesized. The 15,20-triamide analogues with a polar substi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kotoku N,Kato T,Narumi F,Ohtani E,Kamada S,Aoki S,Okada N,Nakagawa S,Kobayashi M

    更新日期:2006-11-15 00:00:00

  • Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.

    abstract::A set of 116 structurally very diverse compounds, mainly drugs, was characterized by 1630 molecular descriptors. The biological property modelled in this study was the transdermal permeability coefficient logK(p). The main objective was to find a limited set of suitable model compounds for skin penetration studies. Th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Baert B,Deconinck E,Van Gele M,Slodicka M,Stoppie P,Bodé S,Slegers G,Vander Heyden Y,Lambert J,Beetens J,De Spiegeleer B

    更新日期:2007-11-15 00:00:00

  • Design, synthesis and biological evaluation of novel 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives as potential cholinesterase inhibitors.

    abstract::Hydroxylated 6H-benzo[c]chromen-6-one derivatives (i.e., urolithins) are the main bioavailable metabolites, and biomarkers of ellagitannins present in various nutrition. Although these dietaries, the sources of urolithins, are employed in folk medicine as cognitive enhancer in the treatment of Alzheimer's Disease, uro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gulcan HO,Unlu S,Esiringu I,Ercetin T,Sahin Y,Oz D,Sahin MF

    更新日期:2014-10-01 00:00:00