Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens.


:Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived.


Bioorg Med Chem


Mazu TK,Etukala JR,Zhu XY,Jacob MR,Khan SI,Walker LA,Ablordeppey SY




Has Abstract


2011-01-01 00:00:00














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    abstract::The syntheses of new nitroimidazole compounds using silicon-[(18)F]fluorine chemistry for the potential detection of tumor hypoxia are described. [(18)F]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic ex...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Joyard Y,Azzouz R,Bischoff L,Papamicaël C,Labar D,Bol A,Bol V,Vera P,Grégoire V,Levacher V,Bohn P

    更新日期:2013-07-01 00:00:00

  • γ-Hydroxyethyl piperidine iminosugar and N-alkylated derivatives: a study of their activity as glycosidase inhibitors and as immunosuppressive agents.

    abstract::An efficient and practical strategy for the synthesis of (3R,4s,5S)-4-(2-hydroxyethyl) piperidine-3,4,5-triol and its N-alkyl derivatives 8a-f, starting from the D-glucose, is reported. The chiral pool methodology involves preparation of the C-3-allyl-α-D-ribofuranodialdose 10, which was converted to the C-5-amino der...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Markad PR,Sonawane DP,Ghosh S,Chopade BA,Kumbhar N,Louat T,Herman J,Waer M,Herdewijn P,Dhavale DD

    更新日期:2014-11-01 00:00:00

  • Synthesis and characterization of a small analogue of the anticancer natural product leinamycin.

    abstract::Leinamycin (1) is a Streptomyces-derived natural product that displays nanomolar IC(50) values against human cancer cell lines. In the work described here, we report the synthesis and characterization of a small leinamycin analogue 19 that closely resembles the 'upper-right quadrant' of the natural product, consisting...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Keerthi K,Rajapakse A,Sun D,Gates KS

    更新日期:2013-01-01 00:00:00

  • New triterpenoid saponins with strong alpha-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana.

    abstract::Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (2-4, 12) and 3, 28-O-bidesmosides (5-7, ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Luo JG,Ma L,Kong LY

    更新日期:2008-03-15 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

  • Bisubstrate Inhibitors of the MYST HATs Esa1 and Tip60.

    abstract::Esa1 (essential Sas2-related acetyltransferase 1) and Tip60 (HIV-1 TAT-interactive protein, 60 kDa) are key members of the MYST family of histone acetyltransferases (HATs) and play important functions in many cellular processes. In this work, we designed, synthesized and evaluated a series of substrate-based analogs f...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wu J,Xie N,Wu Z,Zhang Y,Zheng YG

    更新日期:2009-02-01 00:00:00

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Su J,McKittrick BA,Tang H,Czarniecki M,Greenlee WJ,Hawes BE,O'Neill K

    更新日期:2005-03-01 00:00:00

  • A new small molecule that directly inhibits the DNA binding of NF-kappaB.

    abstract::Nuclear factor-kappaB (NF-kappaB) has been considered as a good target for the treatment of many diseases. Although a lot of NF-kappaB inhibitors have already been reported, many of them have several common problems. Thus, we attempted to identify novel NF-kappaB inhibitors to be unique lead compounds for creating new...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kobayashi T,Yoshimori A,Kino K,Komori R,Miyazawa H,Tanuma SI

    更新日期:2009-07-15 00:00:00

  • Structure-activity relationship study of pyrimido[1,2-c][1,3]benzothiazin-6-imine derivatives for potent anti-HIV agents.

    abstract::3,4-Dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182) is an antiretroviral agent with submicromolar inhibitory activity against human immunodeficiency virus-1 (HIV-1) and HIV-2 infection. In the current study, the structure-activity relationships of accessory groups at the 3- and 9-positions of pyrimi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Mizuhara T,Oishi S,Ohno H,Shimura K,Matsuoka M,Fujii N

    更新日期:2012-11-01 00:00:00

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    abstract::Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Opsenica D,Angelovski G,Pocsfalvi G,Juranić Z,Zizak Z,Kyle D,Milhous WK,Solaja BA

    更新日期:2003-07-03 00:00:00

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    abstract::Dicationic 2,6-diphenylpyrazines, aza-analogues and prodrugs were synthesized; evaluated for DNA affinity, activity against Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.) in vitro, efficacy in T. b. r. STIB900 acute and T. b. brucei GVR35 CNS mouse models. Most diamidines gave poly(dA-dT)2...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hu L,Patel A,Bondada L,Yang S,Wang MZ,Munde M,Wilson WD,Wenzler T,Brun R,Boykin DW

    更新日期:2013-11-01 00:00:00

  • Insect neuropeptides: structures, chemical modifications and potential for insect control.

    abstract::Insect neuropeptides are involved in almost all physiological processes in insects, such as diuresis, ecdysis, pheromone biosynthesis and control of muscle activity. Thus, these small peptide hormones and their receptors are promising targets for a novel generation of selective and non-neurotoxic insecticides. However...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Scherkenbeck J,Zdobinsky T

    更新日期:2009-06-15 00:00:00

  • Identification and characterisation of 2-aminopyridine inhibitors of checkpoint kinase 2.

    abstract::5-(Hetero)aryl-3-(4-carboxamidophenyl)-2-aminopyridine inhibitors of CHK2 were identified from high throughput screening of a kinase-focussed compound library. Rapid exploration of the hits through straightforward chemistry established structure-activity relationships and a proposed ATP-competitive binding mode which ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hilton S,Naud S,Caldwell JJ,Boxall K,Burns S,Anderson VE,Antoni L,Allen CE,Pearl LH,Oliver AW,Wynne Aherne G,Garrett MD,Collins I

    更新日期:2010-01-15 00:00:00

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lewandowska H,Stępkowski TM,Sadło J,Wójciuk GP,Wójciuk KE,Rodger A,Kruszewski M

    更新日期:2012-11-15 00:00:00

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    abstract::Four new palladium(II) complexes with the formula Pd(L)(2), where L are quinoxaline-2-carbonitrile N(1),N(4)-dioxide derivatives, were synthesized as a contribution to the chemistry and pharmacology of metal compounds with this class of pharmacologically interesting bioreductive prodrugs. Compounds were characterized ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Urquiola C,Vieites M,Torre MH,Cabrera M,Lavaggi ML,Cerecetto H,González M,Cerain AL,Monge A,Smircich P,Garat B,Gambino D

    更新日期:2009-02-15 00:00:00

  • Synthesis of egonol derivatives and their antimicrobial activities.

    abstract::Eighteen derivatives of egonol (A-R) were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231 and Escherichia coli ATCC 8739 microorganisms comparing with egonol. The obtained data reported that compound B exhib...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Emirdağ-Öztürk S,Karayildirim T,Anil H

    更新日期:2011-02-01 00:00:00

  • Synthesis of (R)- or (S)-valinol using ω-transaminases in aqueous and organic media.

    abstract::Valinol is part of numerous pharmaceuticals and has various other important applications. Optically pure valinol (ee >99%) was prepared employing different ω-transaminases from the corresponding prochiral hydroxy ketone. By the choice of the enzyme the (R)- as well as the (S)-enantiomer were accessible. Reductive amin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Fuchs CS,Simon RC,Riethorst W,Zepeck F,Kroutil W

    更新日期:2014-10-15 00:00:00

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    abstract::Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Weber A,Döhl K,Sachs J,Nordschild ACM,Schröder D,Kulik A,Fischer T,Schmitt L,Teusch N,Pietruszka J

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Venkateswararao E,Manickam M,Boggu P,Kim Y,Jung SH

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sato I,Morihira K,Inami H,Kubota H,Morokata T,Suzuki K,Iura Y,Nitta A,Imaoka T,Takahashi T,Takeuchi M,Ohta M,Tsukamoto S

    更新日期:2008-09-15 00:00:00

  • Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Webb TR,Lvovskiy D,Kim SA,Ji Xd,Melman N,Linden J,Jacobson KA

    更新日期:2003-01-02 00:00:00

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

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


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

    更新日期:2007-08-01 00:00:00

  • Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Boa AN,Canavan SP,Hirst PR,Ramsey C,Stead AM,McConkey GA

    更新日期:2005-03-15 00:00:00

  • 1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: da Cruz EH,Hussene CM,Dias GG,Diogo EB,de Melo IM,Rodrigues BL,da Silva MG,Valença WO,Camara CA,de Oliveira RN,de Paiva YG,Goulart MO,Cavalcanti BC,Pessoa C,da Silva Júnior EN

    更新日期:2014-03-01 00:00:00

  • Synthesis and cytotoxic activity of novel C7-functionalized spongiane diterpenes.

    abstract::Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hydroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Arnó M,Betancur-Galvis L,González MA,Sierra J,Zaragozá RJ

    更新日期:2003-07-17 00:00:00

  • Design and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling.

    abstract::A novel radioisotope-free photo-affinity probe containing the 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group was designed and synthesized. This very compact functionality is envisaged to allow photochemically-induced coupling of a compound to its target followed by click reaction coupling with an azido-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kumar NS,Young RN

    更新日期:2009-08-01 00:00:00

  • Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives.

    abstract::A series of perbutyrylated glycosides of podophyllotoxin and its derivatives were synthesized and evaluated for their antitumor activity in vitro. Most of them exhibit cytotoxic activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Among the synthesized comp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zi CT,Yang D,Dong FW,Li GT,Li Y,Ding ZT,Zhou J,Jiang ZH,Hu JM

    更新日期:2015-04-01 00:00:00

  • Flavonoids as noncompetitive inhibitors of Dengue virus NS2B-NS3 protease: inhibition kinetics and docking studies.

    abstract::NS2B-NS3 is a serine protease of the Dengue virus considered a key target in the search for new antiviral drugs. In this study flavonoids were found to be inhibitors of NS2B-NS3 proteases of the Dengue virus serotypes 2 and 3 with IC50 values ranging from 15 to 44 μM. Agathisflavone (1) and myricetin (4) turned out to...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: de Sousa LR,Wu H,Nebo L,Fernandes JB,da Silva MF,Kiefer W,Kanitz M,Bodem J,Diederich WE,Schirmeister T,Vieira PC

    更新日期:2015-02-01 00:00:00

  • Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate.

    abstract::Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Dodo K,Minato T,Noguchi-Yachide T,Suganuma M,Hashimoto Y

    更新日期:2008-09-01 00:00:00

  • Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration.

    abstract::Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Acc...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Matralis AN,Xanthopoulos D,Huot G,Lopes-Paciencia S,Cole C,de Vries H,Ferbeyre G,Tsantrizos YS

    更新日期:2018-11-01 00:00:00