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


: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 the pyridine moiety. Structure-activity relationship studies were subsequently conducted over a larger range of 1,4-diarylbutadienes in order to determine the scope of active compounds, to identify structural patterns governing activity and to enhance in vitro potency against E. tenella. In addition, the efficacy of many compounds for treating coccidiosis in chickens was measured by testing the ability of the compound to prevent or reduce intestinal and cecal lesions when administered by oral gavage. A few compounds in the series were identified that exhibited a moderate degree of in vitro and in vivo activity.


Bioorg Med Chem


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




Has Abstract


2003-09-01 00:00:00














  • Biochemical and transcriptional profiling to triage additional activities in a series of IGF-1R/IR inhibitors.

    abstract::Therapeutic development of a targeted agent involves a series of decisions over additional activities that may be ignored, eliminated or pursued. This paper details the concurrent application of two methods that provide a spectrum of information about the biological activity of a compound: biochemical profiling on a l...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ross-Macdonald P,de Silva H,Patel V,Truong A,He A,Neuhaus I,Tilford C,Ji R,Siemers N,Greer A,Carboni J,Gottardis M,Menard K,Lee F,Dodier M,Frennesson D,Sampognaro A,Saulnier M,Trainor G,Vyas D,Zimmermann K,Wittm

    更新日期:2012-03-15 00:00:00

  • Xanthones for melanogenesis inhibition: Molecular docking and QSAR studies to understand their anti-tyrosinase activity.

    abstract::The human skin is constantly exposed to external factors that affect its integrity, UV radiation being one of the main stress factors. The repeated exposure to this radiation leads to increased production of Reactive Oxygen Species (ROS) which activate a series of processes involved in photoaging. Excessive UV exposur...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Rosa GP,Palmeira A,Resende DISP,Almeida IF,Kane-Pagès A,Barreto MC,Sousa E,Pinto MMM

    更新日期:2021-01-01 00:00:00

  • Total syntheses of three copper (II) tetracarboranylphenylporphyrins containing 40 or 80 boron atoms and their biological properties in EMT-6 tumor-bearing mice.

    abstract::Three carboranyltetraphenylporphyrins containing 40 or 80 boron atoms were synthesized and evaluated for their biodistribution and toxicity in EMT-6 tumor-bearing mice. Copper (II) meso-5,10,15,20-tetrakis[3-methoxy-4-(o-carboranylmethoxy)phenyl]porphyrin, 6, and copper (II) meso-5,10,15,20-tetrakis[3-hydroxy-4-(o-car...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wu H,Micca PL,Makar MS,Miura M

    更新日期:2006-08-01 00:00:00

  • Fused-ring structure of decahydroisoquinolin as a novel scaffold for SARS 3CL protease inhibitors.

    abstract::The design and evaluation of a novel decahydroisoquinolin scaffold as an inhibitor for severe acute respiratory syndrome (SARS) chymotrypsin-like protease (3CL(pro)) are described. Focusing on hydrophobic interactions at the S2 site, the decahydroisoquinolin scaffold was designed by connecting the P2 site cyclohexyl g...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Shimamoto Y,Hattori Y,Kobayashi K,Teruya K,Sanjoh A,Nakagawa A,Yamashita E,Akaji K

    更新日期:2015-02-15 00:00:00

  • Novel sulfonamide bearing coumarin scaffolds as selective inhibitors of tumor associated carbonic anhydrase isoforms IX and XII.

    abstract::Four novel scaffolds consisting of total 24 compounds (1a-1o, 2a-2c, 3a-3c and 4a-4c) bearing aromatic sulfonamide and coumarin moieties connected through various linkers were synthesized in order to synergize the inhibition potential of both the moieties against four selected human carbonic anhydrase isoforms (hCA I,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chandak N,Ceruso M,Supuran CT,Sharma PK

    更新日期:2016-07-01 00:00:00

  • Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines.

    abstract::A series of novel twenty-eight rigid 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines were synthesized and evaluated for their topoisomerase inhibitory activity as well as their cytotoxicity against several human cancer cell lines. Generally, hydroxylated compounds (16-18, 22-25, and 29-31) containi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kadayat TM,Song C,Shin S,Magar TB,Bist G,Shrestha A,Thapa P,Na Y,Kwon Y,Lee ES

    更新日期:2015-07-01 00:00:00

  • Synthesis, stability and in vitro dermal evaluation of aminocarbonyloxymethyl esters as prodrugs of carboxylic acid agents.

    abstract::Aminocarbonyloxymethyl esters based on (S)-amino acid carriers were synthesised and evaluated as potential prodrugs of carboxylic acid agents. In addition, the compounds were evaluated as topical prodrugs with the aim of improving the dermal delivery of two non-steroidal anti-inflammatory agents: naproxen and flufenam...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Mendes E,Furtado T,Neres J,Iley J,Jarvinen T,Rautio J,Moreira R

    更新日期:2002-03-01 00:00:00

  • Synthesis and anti-inflammatory activity of indole glucosinolates.

    abstract::The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-i...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Vo QV,Trenerry C,Rochfort S,Wadeson J,Leyton C,Hughes AB

    更新日期:2014-01-15 00:00:00

  • Tryptophan-based fluorophores for studying protein conformational changes.

    abstract::With the continuing interest in deciphering the interplay between protein function and conformational changes, small fluorescence probes will be especially useful for tracking changes in the crowded protein interior space. Presently, we describe the potential utility of six unnatural amino acid fluorescence donors str...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Talukder P,Chen S,Liu CT,Baldwin EA,Benkovic SJ,Hecht SM

    更新日期:2014-11-01 00:00:00

  • Synthesis and evaluation of homo-bivalent GnRHR ligands.

    abstract::G protein coupled receptors (GPCRs) are important drug targets in pharmaceutical research. Traditionally, most research efforts have been devoted towards the design of small molecule agonists and antagonists. An interesting, yet poorly investigated class of GPCR modulators comprise the bivalent ligands, in which two r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Bonger KM,van den Berg RJ,Heitman LH,IJzerman AP,Oosterom J,Timmers CM,Overkleeft HS,van der Marel GA

    更新日期:2007-07-15 00:00:00

  • Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.

    abstract::A methanolic extract and its ethyl acetate-soluble fraction from Sri Lankan curry-leaf, the leaves of Murraya koenigii, inhibited melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Two new carbazole alkaloids, karapinchamines A and B, were isolated from the ethyl acetate-soluble fraction together ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Nakamura S,Nakashima S,Oda Y,Yokota N,Fujimoto K,Matsumoto T,Ohta T,Ogawa K,Maeda S,Nishida S,Matsuda H,Yoshikawa M

    更新日期:2013-03-01 00:00:00

  • DNA double helix destabilizing properties of cyclobisintercaland compounds and competition with a single strand binding protein.

    abstract::The DNA helix destabilizing activity of a series of cyclobisintercaland compounds (CBIs) has been evaluated by measuring their ability to displace a 32P-labelled oligonucleotide primer (17-mer) hybridized to the single stranded DNA of M13. This destabilizing activity appears to be strongly dependent on the cyclic stru...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Teulade-Fichou MP,Fauquet M,Baudoin O,Vigneron JP,Lehn JM

    更新日期:2000-01-01 00:00:00

  • Synthesis and evaluation of amino-threoses in D- and L-series: are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

    abstract::Cyclic D- and L-4-aminothreose were synthesised from ethyl D- and L-tartrate, respectively. D-aminothreose was a potent inhibitor of alpha-glucosidase and of alpha-mannosidase. From the glycosidase inhibition potencies of the four 4-amino-4-deoxy-tetroses, the contribution of binding of each functionality of the 5 and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chevrier C,Defoin A,Tarnus C

    更新日期:2007-06-15 00:00:00

  • Novel designed enediynes: molecular design, chemical synthesis, mode of cycloaromatization and guanine-specific DNA cleavage.

    abstract::The molecular design and chemical synthesis of novel enediyne molecules related to the neocarzinostatin chromophore (1), and their chemical and DNA cleaving properties are described. The 10-membered enediyne triols 16-18 were effectively synthesized from xylitol (10) in a short step, and found to be quite stable when ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Toshima K,Ohta K,Kano T,Nakamura T,Nakata M,Kinoshita M,Matsumura S

    更新日期:1996-01-01 00:00:00

  • Three new bioactive bis-adjacent THF-ring acetogenins from the bark of Annona squamosa.

    abstract::Continuing work on the bioactivity-directed fractionation of the bark of Annona squamosa has resulted in the discovery of three new Annonaceous acetogenins, (2,4-cis and trans)-squamolinone (1), (2,4-cis and trans)-9-oxoasimicinone (2), and bullacin B (3). Compounds 1-3 are all adjacent bis-THF ring acetogenins with 2...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hopp DC,Alali FQ,Gu ZM,McLaughlin JL

    更新日期:1998-05-01 00:00:00

  • Probes for narcotic receptor mediated phenomena. 47. Novel C4a- and N-substituted-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols.

    abstract::A series of N-methyl rac-cis-4a-aralkyl- and alkyl-substituted-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols have been prepared (2a-l) using a simple previously designed synthetic route, in order to find a ligand that would interact with both μ- and δ-opioid receptors. A C4a-phenethyl derivative 2a, was found t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Iyer MR,Rothman RB,Dersch CM,Jacobson AE,Rice KC

    更新日期:2013-06-01 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

  • An efficient preparation of polyanionic affinity agent and its evaluation for the measurement of glycated hemoglobin.

    abstract::An efficient method was developed for the preparation of polyanionic affinity agent (3), a key component in the measurement of glycated hemoglobin (GHb). Glycated hemoglobin is an important clinical marker for diagnosis of patients with diabetes and useful to monitor the management of disease. The affinity agent (3) w...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Reddy RE,Pan Y,Johnson DD,Chen YY,Datwyler SA,Hauptman MS,Thottathil JK

    更新日期:2005-05-16 00:00:00

  • Properties of diacetyl (acetoin) reductase from Bacillus stearothermophilus.

    abstract::The cells of Bacillus stearothermophilus contain an NADH-dependent diacetyl (acetoin) reductase. The enzyme was easily purified to homogeneity, partially characterised, and found to be composed of two subunits with the same molecular weight. In the presence of NADH, it catalyses the stereospecific reduction of diacety...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Giovannini PP,Medici A,Bergamini CM,Rippa M

    更新日期:1996-08-01 00:00:00

  • Synthesis and anticonvulsant activity of new N-Mannich bases derived from 3-(2-fluorophenyl)- and 3-(2-bromophenyl)-pyrrolidine-2,5-diones. Part II.

    abstract::Synthesis and anticonvulsant activity of new N-Mannich bases of 3-(2-fluorophenyl)- and 3-(2-bromophenyl)-pyrrolidine-2,5-diones have been described. Initial anticonvulsant screening was performed in mice after intraperitoneal administration in the maximal electroshock seizure test (MES) and subcutaneous pentylenetetr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Obniska J,Rzepka S,Kamiński K

    更新日期:2012-08-01 00:00:00

  • Binding ability of a thymine-functionalized oligolysine towards nucleic acids.

    abstract::In this Letter, we investigated the binding properties towards nucleic acids of a thymine-functionalized oligolysine, composed of nucleobase-bearing amino acid moieties and underivatized l-lysine residues alternate in the backbone. The basic nucleopeptide proved to be well soluble in water and able to interact with bo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Roviello GN,Musumeci D,D'Alessandro C,Pedone C

    更新日期:2014-02-01 00:00:00

  • Catechol derivatives of aminopyrazine and cell protection against UVB-induced mortality.

    abstract::A series of 5-aryl- and 3,5-bis-aryl-2-amino-1,4-pyrazine derivatives 4 and 6, and related imidazolopyrazinones 7, has been synthesized, the aryl groups of which are catechol and/or phenol substituents. These compounds, tested against human keratinocyte cells stressed by UVB irradiation, showed high antioxidative prop...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Cavalier JF,Burton M,Dussart F,Marchand C,Rees JF,Marchand-Brynaert J

    更新日期:2001-04-01 00:00:00

  • Heptaoxygenated xanthones as anti-austerity agents from Securidaca longepedunculata.

    abstract::In a course of our search for anticancer agent based on a novel anti-austerity strategy, we found that the CHCl3 extract of the roots of Securidaca longepedunculata (Polygalaceae), collected at Democratic Republic of Congo, killed PANC-1 human pancreatic cancer cells preferentially in nutrient-deprived medium (NDM). P...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Dibwe DF,Awale S,Kadota S,Morita H,Tezuka Y

    更新日期:2013-12-15 00:00:00

  • Novel 4-acetamide-2-alkylthio-N-acetanilides resembling nimesulide: Synthesis, cell viability evaluation and in silico studies.

    abstract::Since nimesulide, a nonsteroidal anti-inflammatory drug, is known to be a selective inhibitor of cyclooxygenase-2 and shows activity against cancer cells, there has been much interest in developing related molecules with enhanced anticancer properties. Taking in consideration structural features of nimesulide analogue...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Catarro M,Serrano J,Cavalheiro E,Ramos S,Santos AO,Silvestre S,Almeida P

    更新日期:2017-08-15 00:00:00

  • Dihydrofolate reductase and cell growth activity inhibition by the beta-carboline-benzoquinolizidine plant alkaloid deoxytubulosine from Alangium lamarckii: its potential as an antimicrobial and anticancer agent.

    abstract::Beta-carboline-benzoquinolizidine plant alkaloid deoxytubulosine (DTB) was evaluated and assessed for the first time for its biochemical and biological activity employing the biomarker dihydrofolate reductase (DHFR) (5,6,7,8-tetrahydrofolate: NADP+ oxidoreductase, EC as the probe enzyme, a key target in cance...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Rao KN,Venkatachalam SR

    更新日期:1999-06-01 00:00:00

  • Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 2: optimization of inhibitors of human thymidine phosphorylase and their selectivity with uridine phosphorylase.

    abstract::A series of novel 6-methylene-bridged uracil derivatives have been optimized for clinical use as the inhibitors of human thymidine phosphorylase (TP). We describe their synthesis and evaluation. Introduction of a guanidino or an amidino group enhanced the in vitro inhibitory activity of TP comparing with formerly repo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yano S,Kazuno H,Sato T,Suzuki N,Emura T,Wierzba K,Yamashita J,Tada Y,Yamada Y,Fukushima M,Asao T

    更新日期:2004-07-01 00:00:00

  • A new and efficient synthesis of substituted 6-[(2'-dialkylamino)ethyl] pyrimidine and 4-N,N-dialkyl-6-vinyl-cytosine derivatives and evaluation of their anti-rubella activity.

    abstract::New 6-[(2'-dialkylamino)ethyl]-4(3H)-pyrimidinones were prepared by a multistep procedure starting from acetone dicarboxylic acid diethyl ester and urea derivatives. These compounds were used as starting materials to obtain 4-N,N-dialkyl-6-vinyl-pyrimidine derivatives by an unprecedented tandem C-6 side chain Hofmann-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Saladino R,Ciambecchini U,Maga G,Mastromarino P,Conti C,Botta M

    更新日期:2002-07-01 00:00:00

  • Structure-based approach to falcipain-2 inhibitors: synthesis and biological evaluation of 1,6,7-trisubstituted dihydroisoquinolines and isoquinolines.

    abstract::1,4,7-Trisubstituted isoquinolines were designed, synthesized and evaluated for their inhibition against Plasmodium falciparum cysteine protease falcipain-2. The 1-benzyloxyphenyl-dihydroisoquinoline and -isoquinoline derivatives were found to exhibit better activity against falcipain-2 than their corresponding 1-hydr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Batra S,Sabnis YA,Rosenthal PJ,Avery MA

    更新日期:2003-05-15 00:00:00

  • Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs.

    abstract::A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gibbs JH,Robins LT,Zhou Z,Bobadova-Parvanova P,Cottam M,McCandless GT,Fronczek FR,Vicente MG

    更新日期:2013-09-15 00:00:00

  • Design and synthesis of novel androgen receptor antagonists with sterically bulky icosahedral carboranes.

    abstract::Carboranes (dicarba-closo-dodecaboranes) are a class of carbon-containing polyhedral boron-cluster compounds having remarkable chemical and thermal stability, and hydrophobic character. These features may allow application of carboranes as a new hydrophobic core structure in biologically active molecules that interact...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Goto T,Ohta K,Suzuki T,Ohta S,Endo Y

    更新日期:2005-12-01 00:00:00