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145231-45-4 | Carbamimidothioic acid, N-[(4-chlorophenyl)methyl]-, 3-(1H-imidazol-5-yl)propyl ester
CAS No: 145231-45-4 Catalog No: AG001KP1 MDL No:MFCD00926125
Product Description
Catalog Number:
AG001KP1
Chemical Name:
Carbamimidothioic acid, N-[(4-chlorophenyl)methyl]-, 3-(1H-imidazol-5-yl)propyl ester
CAS Number:
145231-45-4
Molecular Formula:
C14H17ClN4S
Molecular Weight:
308.8296
MDL Number:
MFCD00926125
IUPAC Name:
3-(1H-imidazol-5-yl)propyl N'-[(4-chlorophenyl)methyl]carbamimidothioate
InChI:
InChI=1S/C14H17ClN4S/c15-12-5-3-11(4-6-12)8-18-14(16)20-7-1-2-13-9-17-10-19-13/h3-6,9-10H,1-2,7-8H2,(H2,16,18)(H,17,19)
InChI Key:
UCAIEVHKDLMIFL-UHFFFAOYSA-N
SMILES:
N=C(NCc1ccc(cc1)Cl)SCCCc1cnc[nH]1
UNII:
RKU631JF4H
Properties
Complexity:
306
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
308.086g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
308.828g/mol
Monoisotopic Mass:
308.086g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
92.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3
Literature
| Title | Journal |
|---|---|
| Reversal of oxidative stress by histamine H₃ receptor-ligands in experimental models of schizophrenia. | Arzneimittel-Forschung 20120501 |
| Histamine H₃ receptors modulate depolarization-evoked [³H]-noradrenaline release from rat olfactory bulb slices. | Neuropharmacology 20120201 |
| Histamine 3 receptor activation reduces the expression of neuronal angiotensin II type 1 receptors in the heart. | The Journal of pharmacology and experimental therapeutics 20120101 |
| Deletion and down-regulation of HRH4 gene in gastric carcinomas: a potential correlation with tumor progression. | PloS one 20120101 |
| Protective effects of histamine H3-receptor ligands in schizophrenic behaviors in experimental models. | Pharmacological reports : PR 20120101 |
| Histamine h3 receptor: a novel therapeutic target in alcohol dependence? | Frontiers in systems neuroscience 20120101 |
| Integrative role of the histaminergic system in feeding and taste perception. | Frontiers in systems neuroscience 20120101 |
| Molecular determinants of ligand binding modes in the histamine H(4) receptor: linking ligand-based three-dimensional quantitative structure-activity relationship (3D-QSAR) models to in silico guided receptor mutagenesis studies. | Journal of medicinal chemistry 20111208 |
| The H4 histamine receptor agonist, clobenpropit, suppresses human cholangiocarcinoma progression by disruption of epithelial mesenchymal transition and tumor metastasis. | Hepatology (Baltimore, Md.) 20111101 |
| Role of H4 receptor in histamine-mediated responses in human melanoma. | Melanoma research 20111001 |
| Regulation of ERK2 phosphorylation by histamine in splenocytes. | Immunopharmacology and immunotoxicology 20110601 |
| N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands. | Bioorganic & medicinal chemistry 20110501 |
| Agonist-biased signaling at the histamine H4 receptor: JNJ7777120 recruits β-arrestin without activating G proteins. | Molecular pharmacology 20110401 |
| Histamine H(3) receptor-mediated modulation of perivascular nerve transmission in rat mesenteric arteries. | European journal of pharmacology 20110325 |
| Beneficial interaction between clobenpropit and pyridoxine in prevention of electroshock-induced seizures in mice: lack of histaminergic mechanisms. | Human & experimental toxicology 20110101 |
| Modulation of hematopoiesis through histamine receptor signaling. | Frontiers in bioscience (Scholar edition) 20110101 |
| Attenuated expression of HRH4 in colorectal carcinomas: a potential influence on tumor growth and progression. | BMC cancer 20110101 |
| Histaminergic mechanisms for modulation of memory systems. | Neural plasticity 20110101 |
| Comparison of the pharmacological properties of human and rat histamine H(3)-receptors. | Biochemical pharmacology 20101101 |
| Investigation of 4-piperidinols as novel H3 antagonists. | Bioorganic & medicinal chemistry letters 20101101 |
| Withdrawal from repeated administration of morphine alters histamine-induced anxiogenic effects produced by intra-ventral hippocampal microinjection. | Journal of psychopharmacology (Oxford, England) 20100601 |
| Implementation of a fluorescence-based screening assay identifies histamine H3 receptor antagonists clobenpropit and iodophenpropit as subunit-selective N-methyl-D-aspartate receptor antagonists. | The Journal of pharmacology and experimental therapeutics 20100601 |
| The H3 receptor antagonist clobenpropit protects against Abeta42-induced neurotoxicity in differentiated rat PC12 cells. | Die Pharmazie 20100401 |
| Modeling G protein-coupled receptors for structure-based drug discovery using low-frequency normal modes for refinement of homology models: application to H3 antagonists. | Proteins 20100201 |
| R-(-)-alpha-methylhistamine, a histamine H3 receptor agonist, induces endothelium-dependent vasodilation in rat mesenteric resistance arteries. | Biological & pharmaceutical bulletin 20100101 |
| Histamine H3 and H4 receptor affinity of branched 3-(1H-imidazol-4-yl)propyl N-alkylcarbamates. | Bioorganic & medicinal chemistry letters 20091201 |
| [Effects of clobenpropit and histidine on reinstatement of morphine-induced conditioned place preference]. | Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20091101 |
| The histamine H receptor as a new target for treatment of canine inflammatory skin diseases. | Veterinary dermatology 20091001 |
| Development of a selective and potent radioactive ligand for histamine H(3) receptors: A compound potentially useful for receptor occupancy studies. | Bioorganic & medicinal chemistry letters 20090801 |
| Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: synthesis, pharmacological evaluation, and cross-target QSAR studies. | Bioorganic & medicinal chemistry 20090601 |
| The histamine H4 receptor is functionally expressed on T(H)2 cells. | The Journal of allergy and clinical immunology 20090301 |
| The role of histamine 3 receptors in the control of food intake in a seasonal model of obesity: the Siberian hamster. | Behavioural pharmacology 20090301 |
| Histamine H4 receptor antagonism reduces hapten-induced scratching behaviour but not inflammation. | Experimental dermatology 20090101 |
| H4 histamine receptors mediate cell cycle arrest in growth factor-induced murine and human hematopoietic progenitor cells. | PloS one 20090101 |
| Histamine H4 receptors modulate dendritic cell migration through skin--immunomodulatory role of histamine. | Allergy 20081001 |
| Electrophysiology-based analysis of human histamine H(4) receptor pharmacology using GIRK channel coupling in Xenopus oocytes. | European journal of pharmacology 20080904 |
| Apomorphine-induced turning behavior in 6-hydroxydopamine lesioned rats is increased by histidine and decreased by histidine decarboxylase, histamine H1 and H2 receptor antagonists, and an H3 receptor agonist. | Pharmacology, biochemistry, and behavior 20080901 |
| Substance P is involved in the effect of histamine H3 receptor agonist, Sch 50971 on nasal allergic symptoms in mice. | International immunopharmacology 20080801 |
| Human inflammatory dendritic epidermal cells express a functional histamine H4 receptor. | The Journal of investigative dermatology 20080701 |
| Discovery of novel human histamine H4 receptor ligands by large-scale structure-based virtual screening. | Journal of medicinal chemistry 20080612 |
| Zebrafish: An in vivo model for the study of neurological diseases. | Neuropsychiatric disease and treatment 20080601 |
| 4-benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists. | Journal of medicinal chemistry 20080522 |
| Comparison of the effect of an H(3)-inverse agonist on energy intake and hypothalamic histamine release in normal mice and leptin resistant mice with high fat diet-induced obesity. | Behavioural brain research 20080409 |
| Efficient approaches to S-alkyl-N-alkylisothioureas: syntheses of histamine H3 antagonist clobenpropit and its analogues. | The Journal of organic chemistry 20080321 |
| Carnosine protects against Abeta42-induced neurotoxicity in differentiated rat PC12 cells. | Cellular and molecular neurobiology 20080201 |
| The role of histamine in human mammary carcinogenesis: H3 and H4 receptors as potential therapeutic targets for breast cancer treatment. | Cancer biology & therapy 20080101 |
| Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells. | BMC pharmacology 20080101 |
| Histamine-induced itch and its relationship with pain. | Molecular pain 20080101 |
| Histamine excites neurones in the human submucous plexus through activation of H1, H2, H3 and H4 receptors. | The Journal of physiology 20070901 |
| Histamine downregulates monocyte CCL2 production through the histamine H4 receptor. | The Journal of allergy and clinical immunology 20070801 |
| The human histamine H3 receptor couples to GIRK channels in Xenopus oocytes. | European journal of pharmacology 20070719 |
| Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses. | Immunology 20070601 |
| The histamine H3 receptor antagonist clobenpropit enhances GABA release to protect against NMDA-induced excitotoxicity through the cAMP/protein kinase A pathway in cultured cortical neurons. | European journal of pharmacology 20070601 |
| Histamine H3-receptor agonists and imidazole-based H3-receptor antagonists can be thermodynamically discriminated. | British journal of pharmacology 20070601 |
| Correlation of apparent affinity values from H3-receptor binding assays with apparent affinity (pKapp) and intrinsic activity (alpha) from functional bioassays. | British journal of pharmacology 20070501 |
| Role of histamine in ghrelin-induced gastroprotection against acute gastric lesions. | Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20070401 |
| Histamine augments beta2-adrenoceptor-induced cyclic AMP accumulation in human prostate cancer cells DU-145 independently of known histamine receptors. | Biochemical pharmacology 20070315 |
| [Reversing effect of histamine on neurotoxicity induced by beta-amyloid1-42]. | Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20070301 |
| Pre-synaptic histamine H3 receptors regulate glutamate, but not GABA release in rat thalamus. | Neuropharmacology 20070201 |
| Role of apolipoprotein E in anxiety. | Neural plasticity 20070101 |
| STAT1 phosphorylation and cleavage is regulated by the histamine (H4) receptor in human atopic and non-atopic lymphocytes. | International immunopharmacology 20061001 |
| Constitutive activity of H3 autoreceptors modulates histamine synthesis in rat brain through the cAMP/PKA pathway. | Neuropharmacology 20060901 |
| Detection of multiple H3 receptor affinity states utilizing [3H]A-349821, a novel, selective, non-imidazole histamine H3 receptor inverse agonist radioligand. | British journal of pharmacology 20060701 |
| Effect of endogenous histamine in the ventral hippocampus on fear memory deficits induced by scopolamine as evaluated by step-through avoidance response in rats. | Physiology & behavior 20060415 |
| Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors. | Journal of neurophysiology 20060401 |
| Probing the importance of N-glycosylation for [(3)H] clobenpropit binding to human H (3) receptors expressed in HEK 293 cells . 3. Molecular and chemical aspects of the histamine receptors. | Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20060401 |
| Role of substance P on histamine H(3) antagonist-induced scratching behavior in mice. | Journal of pharmacological sciences 20060401 |
| N-(4-Trifluoromethylphenyl)amide group of the synthetic histamine receptor agonist inhibits nicotinic acetylcholine receptor-mediated catecholamine secretion. | Biochemical pharmacology 20060227 |
| Histamine increases sickle erythrocyte adherence to endothelium. | British journal of haematology 20060201 |
| Histaminergic neurons protect the developing hippocampus from kainic acid-induced neuronal damage in an organotypic coculture system. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20060125 |
| Effects of intracerebroventricular administration of ultra low doses of histaminergic drugs on morphine state-dependent memory of passive avoidance in mice. | Behavioural brain research 20060106 |
| Histamine (H3) receptors modulate the excitatory amino acid receptor response of the vestibular afferents. | Brain research 20051207 |
| Cross state-dependent retrieval between histamine and lithium. | Physiology & behavior 20050915 |
| Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first potent and selective H4 receptor agonist. | The Journal of pharmacology and experimental therapeutics 20050901 |
| G protein-dependent pharmacology of histamine H3 receptor ligands: evidence for heterogeneous active state receptor conformations. | The Journal of pharmacology and experimental therapeutics 20050701 |
| Histamine-3 receptor antagonists reduce superoxide anion generation and lipid peroxidation in rat brain homogenates. | The Journal of pharmacy and pharmacology 20050601 |
| Generation of cell lines for drug discovery through random activation of gene expression: application to the human histamine H3 receptor. | Assay and drug development technologies 20050601 |
| Histamine H4 receptor stimulation suppresses IL-12p70 production and mediates chemotaxis in human monocyte-derived dendritic cells. | Journal of immunology (Baltimore, Md. : 1950) 20050501 |
| Influence of intracerebroventricular administration of histaminergic drugs on morphine state-dependent memory in the step-down passive avoidance test. | Pharmacology 20050501 |
| Effect of combined histamine H1 and H3 receptor blockade on cutaneous microvascular permeability elicited by compound 48/80. | Life sciences 20050304 |
| Inhibition of tryptase release from human colon mast cells by histamine receptor antagonists. | Asian Pacific journal of allergy and immunology 20050301 |
| 2-(4-alkylpiperazin-1-yl)quinolines as a new class of imidazole-free histamine H3 receptor antagonists. | Journal of medicinal chemistry 20050113 |
| Histamine H3 receptors modulate reactive hyperemia in rat gut. | Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20040901 |
| Histamine H3 receptor activation inhibits dopamine D1 receptor-induced cAMP accumulation in rat striatal slices. | Neuroscience letters 20040708 |
| Presynaptic cannabinoid CB(1) receptors are involved in the inhibition of the neurogenic vasopressor response during septic shock in pithed rats. | British journal of pharmacology 20040601 |
| Ligand identification for G-protein-coupled receptors: a lead generation perspective. | Current opinion in chemical biology 20040601 |
| 1-alkyl-4-acylpiperazines as a new class of imidazole-free histamine H(3) receptor antagonists. | Journal of medicinal chemistry 20040520 |
| Effect of the histamine H3-antagonist clobenpropit on spatial memory deficits induced by MK-801 as evaluated by radial maze in Sprague-Dawley rats. | Behavioural brain research 20040505 |
| Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in Balb C mice. | British journal of pharmacology 20040501 |
| Histamine H4 receptor mediates eosinophil chemotaxis with cell shape change and adhesion molecule upregulation. | British journal of pharmacology 20040501 |
| [Mechanisms of the effect of brain histamine on chronic epilepsy induced by pentylenetetrazole]. | Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20040501 |
| Intracerebroventricular administration of histamine H3 receptor antagonists decreases seizures in rat models of epilepsia. | Methods and findings in experimental and clinical pharmacology 20040501 |
| Histamine h3 receptor antagonists potentiate methamphetamine self-administration and methamphetamine-induced accumbal dopamine release. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20040401 |
| Inhibitory effect of iodophenpropit, a selective histamine H3 antagonist, on amygdaloid kindled seizures. | Brain research bulletin 20040315 |
| Involvement of central and peripheral histamine H(3) receptors in the control of the vascular tone and oxygen uptake in the mesenteric circulation of the rat. | Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20040301 |
| Activation of histamine H3 receptors in human nasal mucosa inhibits sympathetic vasoconstriction. | European journal of pharmacology 20040119 |
| Effects of clobenpropit on pentylenetetrazole-kindled seizures in rats. | European journal of pharmacology 20031215 |
| Histamine induces cytoskeletal changes in human eosinophils via the H(4) receptor. | British journal of pharmacology 20031101 |
| Histamine H3 receptors regulate vascular permeability changes in the skin of mast cell-deficient mice. | International immunopharmacology 20031101 |
| Effects of endogenous histamine on seizure development of pentylenetetrazole-induced kindling in rats. | Pharmacology 20030901 |
| Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice. | The British journal of dermatology 20030701 |
| Two novel and selective nonimidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects. | The Journal of pharmacology and experimental therapeutics 20030601 |
| An in vitro study of histamine on the pulmonary artery of the Wistar-Kyoto and spontaneously hypertensive rats. | European journal of pharmacology 20030530 |
| Molecular and pharmacological characterization of the mouse histamine H3 receptor. | European journal of pharmacology 20030425 |
| Novel nonimidazole histamine H3 receptor antagonists: 1-(4-(phenoxymethyl)benzyl)piperidines and related compounds. | Journal of medicinal chemistry 20030410 |
| Replacement of imidazole by a piperidine moiety differentially affects the potency of histamine H3-receptor antagonists. | Naunyn-Schmiedeberg's archives of pharmacology 20030101 |
| Increased brain histamine H3 receptor expression during hibernation in golden-mantled ground squirrels. | BMC neuroscience 20030101 |
| Coordination of histamine H3 receptor antagonists with human adrenal cytochrome P450 enzymes. | Pharmacology 20021101 |
| Activation of the extraneuronal monoamine transporter (EMT) from rat expressed in 293 cells. | British journal of pharmacology 20021101 |
| Characteristics of recombinantly expressed rat and human histamine H3 receptors. | European journal of pharmacology 20021018 |
| Histamine H3 receptor activation inhibits neurogenic sympathetic vasoconstriction in porcine nasal mucosa. | European journal of pharmacology 20021011 |
| Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells. | The Journal of pharmacology and experimental therapeutics 20021001 |
| Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa. | British journal of pharmacology 20020901 |
| Differential in vivo effects of H3 receptor ligands in a new mouse dipsogenia model. | Pharmacology, biochemistry, and behavior 20020601 |
| Presynaptic H3 autoreceptors modulate histamine synthesis through cAMP pathway. | Molecular pharmacology 20020101 |
| Identification of a histamine H4 receptor on human eosinophils--role in eosinophil chemotaxis. | Journal of receptor and signal transduction research 20020101 |
| Constitutive activity of histamine h(3) receptors stably expressed in SK-N-MC cells: display of agonism and inverse agonism by H(3) antagonists. | The Journal of pharmacology and experimental therapeutics 20011201 |
| Dynamics of histamine H(3) receptor antagonists on brain histamine metabolism: do all histamine H(3) receptor antagonists act at a single site? | European journal of pharmacology 20011116 |
| Histamine H3 receptor-mediated impairment of contextual fear conditioning and in-vivo inhibition of cholinergic transmission in the rat basolateral amygdala. | The European journal of neuroscience 20011101 |
| Involvement of central histamine in amygdaloid kindled seizures in rats. | Behavioural brain research 20011015 |
| Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation. | The Journal of pharmacology and experimental therapeutics 20011001 |
| Histaminergic modulation of GABAergic transmission in rat ventromedial hypothalamic neurones. | The Journal of physiology 20010801 |
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| Influence of imidazole replacement in different structural classes of histamine H(3)-receptor antagonists. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20010601 |
| Development of a pharmacophore model for histamine H3 receptor antagonists, using the newly developed molecular modeling program SLATE. | Journal of medicinal chemistry 20010524 |
| Histamine H3 receptor-mediated inhibition of sympathetically evoked mydriasis in rats. | European journal of pharmacology 20010504 |
| Histamine H(3) receptor-mediated inhibition of depolarization-induced, dopamine D(1) receptor-dependent release of [(3)H]-gamma-aminobutryic acid from rat striatal slices. | British journal of pharmacology 20010501 |
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| Genomic organization and characterization of splice variants of the human histamine H3 receptor. | The Biochemical journal 20010415 |
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| Novel histamine H(3)-receptor antagonists and partial agonists with a non-aminergic structure. | British journal of pharmacology 20010401 |
| Effect of clobenpropit on regional cerebral blood flow in rat hippocampus. | Acta pharmacologica Sinica 20010401 |
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| Distinct pharmacology of rat and human histamine H(3) receptors: role of two amino acids in the third transmembrane domain. | British journal of pharmacology 20001201 |
| Identification of a histamine H(3)-like receptor in the zebrafish (Danio rerio) brain. | Journal of neurochemistry 20000801 |
| Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles. | The Journal of pharmacology and experimental therapeutics 20000601 |
| Effects of histamine H3 receptor agonists and antagonists on cognitive performance and scopolamine-induced amnesia. | Behavioural brain research 19991001 |
| Histamine inhibits the production of interleukin-12 through interaction with H2 receptors. | The Journal of clinical investigation 19981115 |
| Effect of interleukin-1beta on the ascending and descending reflex in rat small intestine. | European journal of pharmacology 19981023 |
| Inhibitory H3 receptors on sympathetic nerves of the pithed rat: activation by endogenous histamine and operation in spontaneously hypertensive rats. | Naunyn-Schmiedeberg's archives of pharmacology 19970201 |
| Short photoperiod-induced decrease of histamine H3 receptors facilitates activation of hypothalamic neurons in the Siberian hamster. | Endocrinology |
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