Synthesis, in vivo evaluation, and molecular modeling studies of new pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide derivatives. Identification of a bifunctional hydrogen bond area related to the inverse agonism.

PubWeight™: 0.76‹?›

🔗 View Article (PMID 19591485)

Published in J Med Chem on August 13, 2009

Authors

Gabriella Guerrini1, Giovanna Ciciani, Giovanni Cambi, Fabrizio Bruni, Silvia Selleri, Chiara Guarino, Fabrizio Melani, Marina Montali, Claudia Martini, Carla Ghelardini, Monica Norcini, Annarella Costanzo

Author Affiliations

1: Dipartimento di Scienze Farmaceutiche, Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamente attivi (HeteroBioLab), Università degli Studi di Firenze, Via U. Schiff 6, 50019 Polo Scientifico, Sesto Fiorentino-Firenze, Italy. gabriella.guerrini@unifi.it

Articles citing this

Implications of GABAergic Neurotransmission in Alzheimer's Disease. Front Aging Neurosci (2016) 0.79

Articles by these authors

The orphan receptor GPR17 identified as a new dual uracil nucleotides/cysteinyl-leukotrienes receptor. EMBO J (2006) 2.17

Integration of retroviral vectors induces minor changes in the transcriptional activity of T cells from ADA-SCID patients treated with gene therapy. Blood (2009) 1.88

Oxytocin receptor polymorphisms and adult attachment style in patients with depression. Psychoneuroendocrinology (2009) 1.70

DPA-714, a new translocator protein-specific ligand: synthesis, radiofluorination, and pharmacologic characterization. J Nucl Med (2008) 1.49

Prevention of excessive endothelin-1 release in sclerotherapy: in vitro and in vivo studies. Dermatol Surg (2014) 1.44

The recently identified P2Y-like receptor GPR17 is a sensor of brain damage and a new target for brain repair. PLoS One (2008) 1.44

Sequential gene profiling of basal cell carcinomas treated with imiquimod in a placebo-controlled study defines the requirements for tissue rejection. Genome Biol (2007) 1.38

Plasma and serum brain-derived neurotrophic factor (BDNF) in depressed patients during 1 year of antidepressant treatments. J Affect Disord (2007) 1.38

Degranulation of paneth cells via toll-like receptor 9. Am J Pathol (2004) 1.36

Menthol: a natural analgesic compound. Neurosci Lett (2002) 1.32

The spontaneous Ala147Thr amino acid substitution within the translocator protein influences pregnenolone production in lymphomonocytes of healthy individuals. Endocrinology (2009) 1.27

Cloning, pharmacological characterisation and distribution of the rat G-protein-coupled P2Y(13) receptor. Biochem Pharmacol (2004) 1.26

Insight into 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamides as peripheral benzodiazepine receptor ligands: synthesis, biological evaluation and 3D-QSAR investigation. Bioorg Med Chem (2005) 1.26

Conservation of genetic alterations in recurrent melanoma supports the melanoma stem cell hypothesis. Cancer Res (2008) 1.22

Molecular signatures induced by interleukin-2 on peripheral blood mononuclear cells and T cell subsets. J Transl Med (2006) 1.21

Activation of enteroendocrine cells via TLRs induces hormone, chemokine, and defensin secretion. J Immunol (2007) 1.15

Low molecular weight hyaluronic acid increases the self-defense of skin epithelium by induction of beta-defensin 2 via TLR2 and TLR4. J Immunol (2008) 1.14

Development of ligands for the peripheral benzodiazepine receptor. Curr Med Chem (2006) 1.13

Ala147Thr substitution in translocator protein is associated with adult separation anxiety in patients with depression. Psychiatr Genet (2009) 1.13

Activation of smooth muscle and myenteric plexus cells of jejunum via Toll-like receptor 4. J Cell Physiol (2006) 1.13

Genomic scale analysis of racial impact on response to IFN-alpha. Proc Natl Acad Sci U S A (2009) 1.08

Identification of changes in Triticum durum L. leaf proteome in response to salt stress by two-dimensional electrophoresis and MALDI-TOF mass spectrometry. Anal Bioanal Chem (2008) 1.07

Selective culture of mesodermal progenitor cells. Stem Cells Dev (2009) 1.06

CMV pp65 and IE-1 T cell epitopes recognized by healthy subjects. J Transl Med (2007) 1.06

The oxysterol-CXCR2 axis plays a key role in the recruitment of tumor-promoting neutrophils. J Exp Med (2013) 1.06

Phenotypic changes, signaling pathway, and functional correlates of GPR17-expressing neural precursor cells during oligodendrocyte differentiation. J Biol Chem (2011) 1.05

Morphologic features and glial activation in rat oxaliplatin-dependent neuropathic pain. J Pain (2013) 1.05

Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors. J Med Chem (2012) 1.03

Novel pathogenic mechanisms of congenital insensitivity to pain with anhidrosis genetic disorder unveiled by functional analysis of neurotrophic tyrosine receptor kinase type 1/nerve growth factor receptor mutations. J Biol Chem (2001) 1.03

Oxaliplatin-induced neuropathy: oxidative stress as pathological mechanism. Protective effect of silibinin. J Pain (2012) 1.02

Signaling pathway of morphine induced acute thermal hyperalgesia in mice. Pain (2006) 1.01

Synthesis of new pyrazolo[5,1-c][1,2,4] benzotriazines, pyrazolo[5,1-c]pyrido[4,3-e][1,2,4] triazines and their open analogues as cytotoxic agents in normoxic and hypoxic conditions. Bioorg Med Chem (2008) 0.98

Novel, highly potent adenosine deaminase inhibitors containing the pyrazolo[3,4-d]pyrimidine ring system. Synthesis, structure-activity relationships, and molecular modeling studies. J Med Chem (2005) 0.98

Functional characterization of two isoforms of the P2Y-like receptor GPR17: [35S]GTPgammaS binding and electrophysiological studies in 1321N1 cells. Am J Physiol Cell Physiol (2009) 0.97

[(3-Chlorophenyl)piperazinylpropyl]pyridazinones and analogues as potent antinociceptive agents. J Med Chem (2003) 0.97

Helper B cells promote cytotoxic T cell survival and proliferation independently of antigen presentation through CD27/CD70 interactions. J Immunol (2008) 0.97

A TRPA1 antagonist reverts oxaliplatin-induced neuropathic pain. Sci Rep (2013) 0.95

Synthesis and 3D QSAR of new pyrazolo[3,4-b]pyridines: potent and selective inhibitors of A1 adenosine receptors. J Med Chem (2005) 0.95

Constitutive expression of pluripotency-associated genes in mesodermal progenitor cells (MPCs). PLoS One (2010) 0.95

Peripheral benzodiazepine receptor ligands: mitochondrial transmembrane potential depolarization and apoptosis induction in rat C6 glioma cells. Biochem Pharmacol (2004) 0.95

Identification and purification of mesodermal progenitor cells from human adult bone marrow. Stem Cells Dev (2009) 0.94

Effects of dietary extra-virgin olive oil on behaviour and brain biochemical parameters in ageing rats. Br J Nutr (2010) 0.93

Structure-based optimization of pyrazolo[3,4-d]pyrimidines as Abl inhibitors and antiproliferative agents toward human leukemia cell lines. J Med Chem (2008) 0.93

Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis. J Med Chem (2008) 0.93

Therapeutic synergism of gemcitabine and CpG-oligodeoxynucleotides in an orthotopic human pancreatic carcinoma xenograft. Cancer Res (2005) 0.93

Human glioblastoma multiforme: p53 reactivation by a novel MDM2 inhibitor. PLoS One (2013) 0.93

Different involvement of type 1, 2, and 3 ryanodine receptors in memory processes. Learn Mem (2008) 0.93

Regulation of A2B adenosine receptor functioning by tumour necrosis factor a in human astroglial cells. J Neurochem (2004) 0.93

Protective effect of alpha7 nAChR: behavioural and morphological features on neuropathy. Pain (2010) 0.92

Neuroprotective effects of acetyl-L-carnitine on neuropathic pain and apoptosis: a role for the nicotinic receptor. J Neurosci Res (2009) 0.91

Novel potent 5-HT(3) receptor ligands based on the pyrrolidone structure: synthesis, biological evaluation, and computational rationalization of the ligand-receptor interaction modalities. Bioorg Med Chem (2002) 0.91

Therapeutic efficacy of cord blood-derived mesenchymal stromal cells for the prevention of acute graft-versus-host disease in a xenogenic mouse model. Stem Cells Dev (2011) 0.91

Arylpiperazinylalkylpyridazinones and analogues as potent and orally active antinociceptive agents: synthesis and studies on mechanism of action. J Med Chem (2006) 0.91

Regulation of PC12 cell survival and differentiation by the new P2Y-like receptor GPR17. Cell Signal (2010) 0.91

Benzodiazepine receptor ligands. 8: synthesis and pharmacological evaluation of new pyrazolo[5,1-c] [1,2,4]benzotriazine 5-oxide 3- and 8-disubstituted: high affinity ligands endowed with inverse-agonist pharmacological efficacy. Bioorg Med Chem (2005) 0.91

Development, characterization and in vivo evaluation of benzocaine-loaded liposomes. Eur J Pharm Biopharm (2007) 0.91

N,N-dialkyl-2-phenylindol-3-ylglyoxylamides. A new class of potent and selective ligands at the peripheral benzodiazepine receptor. J Med Chem (2004) 0.90

Effect of preparation technique on the properties and in vivo efficacy of benzocaine-loaded ethosomes. J Liposome Res (2009) 0.90

Frontal affinity chromatography-mass spectrometry useful for characterization of new ligands for GPR17 receptor. J Med Chem (2010) 0.90

New fluoro derivatives of the pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide system: evaluation of fluorine binding properties in the benzodiazepine site on γ-aminobutyrric acid type A (GABA(A)) receptor. Design, synthesis, biological, and molecular modeling investigation. J Med Chem (2010) 0.90

Ethyl 8-fluoro-6-(3-nitrophenyl)-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate as novel, highly potent, and safe antianxiety agent. J Med Chem (2008) 0.89

4-amino-5-substituted-3(2H)-pyridazinones as orally active antinociceptive agents: synthesis and studies on the mechanism of action. J Med Chem (2007) 0.89

Alpha-2 agonist-induced memory impairment is mediated by the alpha-2A-adrenoceptor subtype. Behav Brain Res (2004) 0.89

Mesodermal progenitor cells (MPCs) differentiate into mesenchymal stromal cells (MSCs) by activation of Wnt5/calmodulin signalling pathway. PLoS One (2011) 0.89

Combining galantamine and memantine in multitargeted, new chemical entities potentially useful in Alzheimer's disease. J Med Chem (2012) 0.88

Pleiotropic effect of histamine H4 receptor modulation in the central nervous system. Neuropharmacology (2013) 0.88

Regulation of A(2A) adenosine receptor expression and functioning following permanent focal ischemia in rat brain. J Neurochem (2007) 0.88

Low dose native type II collagen prevents pain in a rat osteoarthritis model. BMC Musculoskelet Disord (2013) 0.88

5'-Carbamoyl derivatives of 2'-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 receptor from different species. Bioorg Med Chem (2007) 0.88

New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists. Bioorg Med Chem Lett (2007) 0.88

A smart platform for hyperthermia application in cancer treatment: cobalt-doped ferrite nanoparticles mineralized in human ferritin cages. ACS Nano (2014) 0.88

Novel N2-substituted pyrazolo[3,4-d]pyrimidine adenosine A3 receptor antagonists: inhibition of A3-mediated human glioblastoma cell proliferation. J Med Chem (2010) 0.87

Receptor crosstalk: haloperidol treatment enhances A(2A) adenosine receptor functioning in a transfected cell model. Purinergic Signal (2010) 0.87

Alpha2-agonists as analgesic agents. Med Res Rev (2009) 0.87

Regulation of Erythropoietin Receptor Activity in Endothelial Cells by Different Erythropoietin (EPO) Derivatives: An in Vitro Study. Int J Mol Sci (2013) 0.87

Molecular interaction in the mouse PAG between NMDA and opioid receptors in morphine-induced acute thermal nociception. J Neurochem (2007) 0.87

Synthesis and biological evaluation of 4-phenylquinazoline-2-carboxamides designed as a novel class of potent ligands of the translocator protein. J Med Chem (2012) 0.87

TSPO over-expression increases motility, transmigration and proliferation properties of C6 rat glioma cells. Biochim Biophys Acta (2007) 0.87

The GABAA-BZR complex as target for the development of anxiolytic drugs. Curr Top Med Chem (2012) 0.86