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  1. Article ; Online: Design and synthesis of reboxetine analogs morpholine derivatives as selective norepinephrine reuptake inhibitors.

    Xu, Wenjian / Gray, David L / Glase, Shelly A / Barta, Nancy S

    Bioorganic & medicinal chemistry letters

    2008  Volume 18, Issue 20, Page(s) 5550–5553

    Abstract: As part of a discovery effort aimed at identifying novel norepinephrine reuptake inhibitors (NRIs), a number of substituted morpholines were designed and synthesized. The target compounds contain vicinal stereogenic centers, and the program was greatly ... ...

    Abstract As part of a discovery effort aimed at identifying novel norepinephrine reuptake inhibitors (NRIs), a number of substituted morpholines were designed and synthesized. The target compounds contain vicinal stereogenic centers, and the program was greatly facilitated by the adoption of efficient synthetic routes which allowed for the late stage incorporation of structural and physicochemical diversity into the targets. Structure-activity relationships were developed by optimizing individual ring components of the structure for NRI potency and for selectivity against other monoamine reuptake transporters. Several novel morpholine derivatives with a potent and selective NRI profile are described.
    MeSH term(s) Adrenergic Uptake Inhibitors/chemical synthesis ; Adrenergic Uptake Inhibitors/pharmacology ; Central Nervous System Agents/chemistry ; Chemistry, Pharmaceutical/methods ; Drug Design ; Humans ; Ketones/chemistry ; Models, Chemical ; Morpholines/chemical synthesis ; Morpholines/chemistry ; Morpholines/pharmacology ; Norepinephrine/antagonists & inhibitors ; Norepinephrine/chemistry ; Stereoisomerism ; Structure-Activity Relationship ; Toluene/chemistry
    Chemical Substances Adrenergic Uptake Inhibitors ; Central Nervous System Agents ; Ketones ; Morpholines ; Toluene (3FPU23BG52) ; morpholine (8B2ZCK305O) ; reboxetine (947S0YZ36I) ; Norepinephrine (X4W3ENH1CV)
    Language English
    Publishing date 2008-10-15
    Publishing country England
    Document type Journal Article
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2008.09.007
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Oligonucleotide tagging for copper-free click conjugation.

    Jawalekar, Anup M / Malik, Sudip / Verkade, Jorge M M / Gibson, Brian / Barta, Nancy S / Hodges, John C / Rowan, Alan / van Delft, Floris L

    Molecules (Basel, Switzerland)

    2013  Volume 18, Issue 7, Page(s) 7346–7363

    Abstract: Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while ... ...

    Abstract Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while the reported cyclooctynes are large and hydrophobic. In this work, it is demonstrated that the introduction of bicyclo[6.1.0]nonyne (BCN) into synthetic oligonucleotides is feasible by standard solid-phase phosphoramidite chemistry. A range of phosphoramidite building blocks is presented for incoporation of BCN or azide, either on-support or in solution. The usefulness of the approach is demonstrated by the straightforward and high-yielding conjugation of the resulting oligonucleotides, including biotinylation, fluorescent labeling, dimerization and attachment to polymer.
    MeSH term(s) Azides/chemistry ; Catalysis ; Click Chemistry ; Copper/chemistry ; Molecular Structure ; Oligonucleotides/chemistry ; Stereoisomerism
    Chemical Substances Azides ; Oligonucleotides ; Copper (789U1901C5)
    Language English
    Publishing date 2013-06-24
    Publishing country Switzerland
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules18077346
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Derivatives of (3S)-N-(biphenyl-2-ylmethyl)pyrrolidin-3-amine as selective noradrenaline reuptake inhibitors: Reducing P-gp mediated efflux by modulation of H-bond acceptor capacity.

    Fish, Paul V / Barta, Nancy S / Gray, David L F / Ryckmans, Thomas / Stobie, Alan / Wakenhut, Florian / Whitlock, Gavin A

    Bioorganic & medicinal chemistry letters

    2008  Volume 18, Issue 15, Page(s) 4355–4359

    Abstract: Derivatives of (3S)-N-(biphenyl-2-ylmethyl)pyrrolidin-3-amine are disclosed as a new series of noradrenaline reuptake inhibitors (NRI). Carboxamide 9e, carbamate 11b and sulfonamide 13a were identified as potent NRIs with excellent selectivity over SRI ... ...

    Abstract Derivatives of (3S)-N-(biphenyl-2-ylmethyl)pyrrolidin-3-amine are disclosed as a new series of noradrenaline reuptake inhibitors (NRI). Carboxamide 9e, carbamate 11b and sulfonamide 13a were identified as potent NRIs with excellent selectivity over SRI and DRI, good in vitro metabolic stability and weak CYP inhibition. Carbamate 11b demonstrated superior transit performance in MDCK-mdr1 cell lines with minimal P-gp efflux which was attributed to reduced HBA capacity of the carbamate group. Evaluation in vivo, in rat microdialysis experiments, showed 11b increased noradrenaline levels by 400% confirming good CNS penetration.
    MeSH term(s) Animals ; Central Nervous System/drug effects ; Combinatorial Chemistry Techniques ; Humans ; Microsomes, Liver/drug effects ; Microsomes, Liver/metabolism ; Molecular Structure ; Pyrrolidines/chemical synthesis ; Pyrrolidines/chemistry ; Pyrrolidines/pharmacology ; Rats ; Serotonin Uptake Inhibitors/chemical synthesis ; Serotonin Uptake Inhibitors/chemistry ; Serotonin Uptake Inhibitors/pharmacology ; Stereoisomerism
    Chemical Substances PF-3609113 ; Pyrrolidines ; Serotonin Uptake Inhibitors
    Language English
    Publishing date 2008-08-01
    Publishing country England
    Document type Journal Article
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2008.06.071
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  4. Article ; Online: Synthesis and pharmacological evaluation of aminopyrimidine series of 5-HT1A partial agonists.

    Dounay, Amy B / Barta, Nancy S / Bikker, Jack A / Borosky, Susan A / Campbell, Brian M / Crawford, Terry / Denny, Lynne / Evans, Lori M / Gray, David L / Lee, Pil / Lenoir, Edward A / Xu, Wenjian

    Bioorganic & medicinal chemistry letters

    2009  Volume 19, Issue 4, Page(s) 1159–1163

    Abstract: Aminopyrimidine 2 (4-(1-(2-(1H-indol-3-yl)ethyl)piperidin-3-yl)-N-cyclopropylpyrimidin-2-amine) emerged from a high throughput screen as a novel 5-HT(1A) agonist. This compound showed moderate potency for 5-HT(1A) in binding and functional assays, as ... ...

    Abstract Aminopyrimidine 2 (4-(1-(2-(1H-indol-3-yl)ethyl)piperidin-3-yl)-N-cyclopropylpyrimidin-2-amine) emerged from a high throughput screen as a novel 5-HT(1A) agonist. This compound showed moderate potency for 5-HT(1A) in binding and functional assays, as well as moderate metabolic stability. Implementation of a strategy for improving metabolic stability by lowering the lipophilicity (cLogD) led to identification of methyl ether 31 (4-(1-(2-(1H-indol-3-yl)ethyl)piperidin-3-yl)-N-(2-methoxyethyl)pyrimidin-2-amine) as a substantially improved compound within the series.
    MeSH term(s) Buspirone/pharmacology ; Combinatorial Chemistry Techniques ; Drug Design ; Humans ; Indoles/chemical synthesis ; Indoles/chemistry ; Indoles/pharmacology ; Microsomes, Liver/drug effects ; Microsomes, Liver/metabolism ; Molecular Structure ; Pyrimidines/chemical synthesis ; Pyrimidines/chemistry ; Pyrimidines/pharmacology ; Receptor, Serotonin, 5-HT1A/drug effects ; Serotonin Receptor Agonists/chemical synthesis ; Serotonin Receptor Agonists/chemistry ; Serotonin Receptor Agonists/pharmacology ; Structure-Activity Relationship
    Chemical Substances 4-(1-(2-(1H-indol-3-yl)ethyl)piperidin-3-yl)-N-(2-methoxyethyl)pyrimidin-2-amine ; 4-(1-(2-(1H-indol-3-yl)ethyl)piperidin-3-yl)-N-cyclopropylpyrimidin-2-amine ; Indoles ; Pyrimidines ; Serotonin Receptor Agonists ; Receptor, Serotonin, 5-HT1A (112692-38-3) ; Buspirone (TK65WKS8HL)
    Language English
    Publishing date 2009-02-15
    Publishing country England
    Document type Journal Article
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2008.12.087
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  5. Article ; Online: Design, synthesis, and pharmacological evaluation of phenoxy pyridyl derivatives as dual norepinephrine reuptake inhibitors and 5-HT1A partial agonists.

    Dounay, Amy B / Barta, Nancy S / Campbell, Brian M / Coleman, Corey / Collantes, Elizabeth M / Denny, Lynne / Dutta, Satavisha / Gray, David L / Hou, Dongfeng / Iyer, Rathna / Maiti, Samarendra N / Ortwine, Daniel F / Probert, Al / Stratman, Nancy C / Subedi, Rajendra / Whisman, Tammy / Xu, Wenjian / Zoski, Kim

    Bioorganic & medicinal chemistry letters

    2010  Volume 20, Issue 3, Page(s) 1114–1117

    Abstract: Preclinical studies suggest that compounds with dual norepinephrine reuptake inhibitor (NRI) and 5-HT(1A) partial agonist properties may provide an important new therapeutic approach to ADHD, depression, and anxiety. Reported herein is the discovery of a ...

    Abstract Preclinical studies suggest that compounds with dual norepinephrine reuptake inhibitor (NRI) and 5-HT(1A) partial agonist properties may provide an important new therapeutic approach to ADHD, depression, and anxiety. Reported herein is the discovery of a novel chemical series with a favorable NRI and 5-HT(1A) partial agonist pharmacological profile as well as excellent selectivity for the norepinephrine transporter over the dopamine transporter.
    MeSH term(s) Adrenergic Uptake Inhibitors/chemical synthesis ; Adrenergic Uptake Inhibitors/metabolism ; Adrenergic Uptake Inhibitors/pharmacology ; Cell Line ; Crystallography, X-Ray ; Drug Design ; Drug Evaluation, Preclinical/methods ; Humans ; Microsomes, Liver/drug effects ; Microsomes, Liver/metabolism ; Norepinephrine Plasma Membrane Transport Proteins/antagonists & inhibitors ; Norepinephrine Plasma Membrane Transport Proteins/metabolism ; Phenols/chemical synthesis ; Phenols/metabolism ; Phenols/pharmacology ; Pyridines/chemical synthesis ; Pyridines/metabolism ; Pyridines/pharmacology ; Receptor, Serotonin, 5-HT1A/metabolism ; Serotonin 5-HT1 Receptor Agonists ; Serotonin Receptor Agonists/chemical synthesis ; Serotonin Receptor Agonists/metabolism ; Serotonin Receptor Agonists/pharmacology
    Chemical Substances Adrenergic Uptake Inhibitors ; Norepinephrine Plasma Membrane Transport Proteins ; Phenols ; Pyridines ; Serotonin 5-HT1 Receptor Agonists ; Serotonin Receptor Agonists ; Receptor, Serotonin, 5-HT1A (112692-38-3) ; phenoxy radical (3229-70-7)
    Language English
    Publishing date 2010-02-01
    Publishing country England
    Document type Comparative Study ; Journal Article
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2009.12.023
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  6. Article: Design, synthesis, and biological activity of novel polycyclic aza-amide FKBP12 ligands.

    Hudack, Raymond A / Barta, Nancy S / Guo, Chuangxing / Deal, Judith / Dong, Liming / Fay, Lorraine K / Caprathe, Bradley / Chatterjee, Arindam / Vanderpool, Darin / Bigge, Christopher / Showalter, Richard / Bender, Steve / Augelli-Szafran, Corinne E / Lunney, Elizabeth / Hou, Xinjun

    Journal of medicinal chemistry

    2006  Volume 49, Issue 3, Page(s) 1202–1206

    Abstract: Since the discovery that FK-506 promotes neurite outgrowth, considerable attention has been focused on the development of potent nonimmunosuppressive ligands for FK-506 binding proteins (FKBPs). Such neuroimmunophilin agents have been reported to show ... ...

    Abstract Since the discovery that FK-506 promotes neurite outgrowth, considerable attention has been focused on the development of potent nonimmunosuppressive ligands for FK-506 binding proteins (FKBPs). Such neuroimmunophilin agents have been reported to show neuroregenerative activity in a variety of cell and animal models including neurite outgrowth, age-related cognitive decline, Parkinson's disease, peripheral nerve injury, optic nerve degeneration, and diabetic neuropathy. We have designed and synthesized a unique series of tetracyclic aza-amides that have been shown to be potent FKBP12 rotamase inhibitors. The structure-activity relationships established in this study have demonstrated diverse structural modifications that result in potent rotamase inhibitory activity.
    MeSH term(s) Amides/chemical synthesis ; Amides/chemistry ; Aza Compounds/chemical synthesis ; Aza Compounds/chemistry ; Binding Sites ; Heterocyclic Compounds, 4 or More Rings/chemical synthesis ; Heterocyclic Compounds, 4 or More Rings/chemistry ; Hydrogen Bonding ; Isoquinolines/chemical synthesis ; Isoquinolines/chemistry ; Ligands ; Neuroprotective Agents/chemical synthesis ; Neuroprotective Agents/chemistry ; Structure-Activity Relationship ; Tacrolimus/chemistry ; Tacrolimus Binding Protein 1A/antagonists & inhibitors ; Tacrolimus Binding Protein 1A/chemistry
    Chemical Substances Amides ; Aza Compounds ; Heterocyclic Compounds, 4 or More Rings ; Isoquinolines ; Ligands ; Neuroprotective Agents ; Tacrolimus Binding Protein 1A (EC 5.2.1.-) ; Tacrolimus (WM0HAQ4WNM)
    Language English
    Publishing date 2006-02-09
    Publishing country United States
    Document type Journal Article
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/jm049161u
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    Zs.MB 1: Show issues

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  7. Article: Carboxylate bioisosteres of pregabalin.

    Schwarz, Jacob B / Colbry, Norman L / Zhu, Zhijian / Nichelson, Brian / Barta, Nancy S / Lin, Kristin / Hudack, Raymond A / Gibbons, Sian E / Galatsis, Paul / DeOrazio, Russell J / Manning, David D / Vartanian, Mark G / Kinsora, Jack J / Lotarski, Susan M / Li, Zheng / Dickerson, Melvin R / El-Kattan, Ayman / Thorpe, Andrew J / Donevan, Sean D /
    Taylor, Charles P / Wustrow, David J

    Bioorganic & medicinal chemistry letters

    2006  Volume 16, Issue 13, Page(s) 3559–3563

    Abstract: Several beta-amino tetrazole analogs of gabapentin 1 and pregabalin 2 were prepared by one of two convergent, highly efficient routes, and their affinity for the alpha(2)-delta protein examined. Two select compounds with potent affinity for alpha(2)- ... ...

    Abstract Several beta-amino tetrazole analogs of gabapentin 1 and pregabalin 2 were prepared by one of two convergent, highly efficient routes, and their affinity for the alpha(2)-delta protein examined. Two select compounds with potent affinity for alpha(2)-delta, 8a and 16a, were subsequently tested in vivo in an audiogenic seizure model and found to elicit protective effects.
    MeSH term(s) Amines/chemical synthesis ; Amines/chemistry ; Amines/pharmacology ; Animals ; Anticonvulsants/chemical synthesis ; Anticonvulsants/chemistry ; Anticonvulsants/pharmacology ; Binding Sites ; Carboxylic Acids/chemistry ; Cyclohexanecarboxylic Acids/chemical synthesis ; Cyclohexanecarboxylic Acids/chemistry ; Cyclohexanecarboxylic Acids/pharmacology ; Disease Models, Animal ; Drug Evaluation, Preclinical ; Epilepsy, Reflex/prevention & control ; Mice ; Mice, Inbred DBA ; Molecular Structure ; Pregabalin ; Protein Subunits/drug effects ; Stereoisomerism ; Structure-Activity Relationship ; gamma-Aminobutyric Acid/analogs & derivatives ; gamma-Aminobutyric Acid/chemical synthesis ; gamma-Aminobutyric Acid/chemistry ; gamma-Aminobutyric Acid/pharmacology
    Chemical Substances Amines ; Anticonvulsants ; Carboxylic Acids ; Cyclohexanecarboxylic Acids ; Protein Subunits ; Pregabalin (55JG375S6M) ; gamma-Aminobutyric Acid (56-12-2) ; gabapentin (6CW7F3G59X)
    Language English
    Publishing date 2006-07-01
    Publishing country England
    Document type Journal Article
    ZDB-ID 1063195-1
    ISSN 1464-3405 ; 0960-894X
    ISSN (online) 1464-3405
    ISSN 0960-894X
    DOI 10.1016/j.bmcl.2006.03.083
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