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Home > Indoles and Oxindole > 84-26-4
84-26-4 | Indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13-dihydro-
CAS No: 84-26-4 Catalog No: AG00IDCD MDL No:MFCD00210551
Product Description
Catalog Number:
AG00IDCD
Chemical Name:
Indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13-dihydro-
CAS Number:
84-26-4
Molecular Formula:
C18H13N3O
Molecular Weight:
287.3153
MDL Number:
MFCD00210551
IUPAC Name:
3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
InChI:
InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
InChI Key:
ACVGWSKVRYFWRP-UHFFFAOYSA-N
SMILES:
O=c1c2ccccc2nc2n1CCc1c2[nH]c2c1cccc2
UNII:
8XZV289PRY
NSC Number:
258317
Properties
Complexity:
517
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
287.106g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
287.322g/mol
Monoisotopic Mass:
287.106g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
48.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3
Literature
| Title | Journal |
|---|---|
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| Simultaneous determination and pharmacokinetic analysis of seven alkaloids and two flavonoids from rat plasma by HPLC-DAD after oral administration of Wuzhuyu decoction. | Journal of Asian natural products research 20120101 |
| New glycosidic alkaloid from the nearly ripe fruits of Euodia rutaecarpa. | Journal of Asian natural products research 20120101 |
| In vitro cellular uptake of evodiamine and rutaecarpine using a microemulsion. | International journal of nanomedicine 20120101 |
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| Bicyclic 1,2,3-triazolium ionic liquids: synthesis, characterization, and application to rutaecarpine synthesis. | Organic letters 20110819 |
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| Reversal of isoprenaline-induced cardiac remodeling by rutaecarpine via stimulation of calcitonin gene-related peptide production. | Canadian journal of physiology and pharmacology 20101001 |
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| Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO. | Journal of cellular biochemistry 20100815 |
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| Accelerated senescence of endothelial progenitor cells in hypertension is related to the reduction of calcitonin gene-related peptide. | Journal of hypertension 20100501 |
| Synthesis and evaluation of novel rutaecarpine derivatives and related alkaloids derivatives as selective acetylcholinesterase inhibitors. | European journal of medicinal chemistry 20100401 |
| Pharmacological effects of rutaecarpine as a cardiovascular protective agent. | Molecules (Basel, Switzerland) 20100315 |
| Synthesis and biological properties of benzo-annulated rutaecarpines. | Biological & pharmaceutical bulletin 20100101 |
| Up-regulation of CYP1A1 by rutaecarpine is dependent on aryl hydrocarbon receptor and calcium. | Toxicology 20091221 |
| Rutecarpine ameliorates bodyweight gain through the inhibition of orexigenic neuropeptides NPY and AgRP in mice. | Biochemical and biophysical research communications 20091120 |
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| [Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091101 |
| Effects of evodiamine and rutaecarpine on the secretion of corticosterone by zona fasciculata-reticularis cells in male rats. | Journal of cellular biochemistry 20091001 |
| Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. | Nature chemical biology 20091001 |
| A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine. | The Journal of organic chemistry 20090807 |
| Calcitonin gene-related peptide mediates the cardioprotective effects of rutaecarpine against ischaemia-reperfusion injury in spontaneously hypertensive rats. | Clinical and experimental pharmacology & physiology 20090701 |
| Isolation of secondary metabolites from Hortia oreadica (Rutaceae) leaves through high-speed counter-current chromatography. | Journal of chromatography. A 20090508 |
| Evodiamine and rutaecarpine inhibit migration by LIGHT via suppression of NADPH oxidase activation. | Journal of cellular biochemistry 20090501 |
| [Study on vitro release and transdermal behaviors of Yulian cataplasm]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090401 |
| Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1). | Bioorganic & medicinal chemistry 20090315 |
| Involvement of prolylcarboxypeptidase in the effect of rutaecarpine on the regression of mesenteric artery hypertrophy in renovascular hypertensive rats. | Clinical and experimental pharmacology & physiology 20090301 |
| The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model. | Phytotherapy research : PTR 20090101 |
| Rutaecarpine inhibits hypoxia/reoxygenation-induced apoptosis in rat hippocampal neurons. | Neuropharmacology 20081201 |
| Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection. | Journal of pharmaceutical and biomedical analysis 20081201 |
| Solid dispersion of rutaecarpine improved its antihypertensive effect in spontaneously hypertensive rats. | Biopharmaceutics & drug disposition 20081201 |
| Calcitonin gene-related peptide-mediated antihypertensive and anti-platelet effects by rutaecarpine in spontaneously hypertensive rats. | Peptides 20081001 |
| Reduction of asymmetric dimethylarginine in the protective effects of rutaecarpine on gastric mucosal injury. | Canadian journal of physiology and pharmacology 20081001 |
| Induction of NAD(P)H: quinone reductase by rutaecarpine isolated from the fruits of Evodia rutaecarpa in the murine hepatic Hepa-1c1c7 cell line. | Planta medica 20080901 |
| Rutaecarpine induces chloride secretion across rat isolated distal colon. | The Journal of pharmacology and experimental therapeutics 20080401 |
| One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine. | Chemical & pharmaceutical bulletin 20080401 |
| Progress in the studies on rutaecarpine. | Molecules (Basel, Switzerland) 20080206 |
| Molecular authentication and quality control using a high performance liquid chromatography technique of Fructus Evodiae. | Biological & pharmaceutical bulletin 20080201 |
| Calcitonin gene-related Peptide-mediated depressor effect and inhibiting vascular hypertrophy of rutaecarpine in renovascular hypertensive rats. | Journal of cardiovascular pharmacology 20071201 |
| The effects of rutaecarpine on the pharmacokinetics of acetaminophen in rats. | Archives of pharmacal research 20071201 |
| [Methodological studies on equivalent relationship between granule for clinical prescription and clinical decoction of fructus evodiae]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070601 |
| Short communication: in vivo evaluation of microemulsion system for oral and parenteral delivery of rutaecarpine to rats. | Drug development and industrial pharmacy 20070501 |
| Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells. | European journal of pharmacology 20070126 |
| Radical reactions with 3H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin. | Organic & biomolecular chemistry 20070107 |
| In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents. | Biological & pharmaceutical bulletin 20070101 |
| Chemical and biological comparisons on Evodia with two related species of different locations and conditions. | Journal of ethnopharmacology 20061124 |
| Elimination of rutaecarpine and its metabolites in rat feces and urine measured by liquid chromatography. | Biomedical chromatography : BMC 20061101 |
| Immunosuppressive effects of rutaecarpine in female BALB/c mice. | Toxicology letters 20060701 |
| Determination of evodiamine and rutecarpine in human serum by liquid chromatography-tandem mass spectrometry. | Analytical and bioanalytical chemistry 20060701 |
| Oxidative metabolism of the alkaloid rutaecarpine by human cytochrome P450. | Drug metabolism and disposition: the biological fate of chemicals 20060501 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Characterization of human liver cytochrome P450 enzymes involved in the metabolism of rutaecarpine. | Journal of pharmaceutical and biomedical analysis 20060411 |
| Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine. | Journal of dermatological science 20060401 |
| Anti-inflammatory principles from the fruits of Evodia rutaecarpa and their cellular action mechanisms. | Archives of pharmacal research 20060401 |
| Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species. | Journal of separation science 20060301 |
| Characterization of the Phase II metabolites of rutaecarpine in rat by liquid chromatography-electrospray ionization-tandem mass spectrometry. | Xenobiotica; the fate of foreign compounds in biological systems 20051201 |
| Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. | Current drug metabolism 20051001 |
| Physicochemical characterization of rutaecarpine-loaded microemulsion system. | Drug development and industrial pharmacy 20050801 |
| Effects of Evodia rutaecarpa and rutaecarpine on the pharmacokinetics of caffeine in rats. | Planta medica 20050701 |
| Identification of the microsomal oxidation metabolites of rutaecarpine, a main active alkaloid of the medicinal herb Evodia rutaecarpa. | Journal of chromatography. A 20050527 |
| The protective effects of rutaecarpine on gastric mucosa injury in rats. | Planta medica 20050501 |
| Evodiamine abolishes constitutive and inducible NF-kappaB activation by inhibiting IkappaBalpha kinase activation, thereby suppressing NF-kappaB-regulated antiapoptotic and metastatic gene expression, up-regulating apoptosis, and inhibiting invasion. | The Journal of biological chemistry 20050429 |
| Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine. | European journal of medicinal chemistry 20050301 |
| Involvement of CGRP in the inhibitory effect of rutaecarpine on vasoconstriction induced by anaphylaxis in guinea pig. | Regulatory peptides 20050215 |
| Alteration of the pharmacokinetics of theophylline by rutaecarpine, an alkaloid of the medicinal herb Evodia rutaecarpa, in rats. | The Journal of pharmacy and pharmacology 20050201 |
| Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract. | Drug metabolism and pharmacokinetics 20050201 |
| Protective effects of rutaecarpine in cardiac anaphylactic injury is mediated by CGRP. | Planta medica 20041201 |
| Inhibition of UVA irradiation-modulated signaling pathways by rutaecarpine, a quinazolinocarboline alkaloid, in human keratinocytes. | European journal of pharmacology 20040913 |
| Stimulation of calcitonin gene-related peptide synthesis and release: mechanisms for a novel antihypertensive drug, rutaecarpine. | Journal of hypertension 20040901 |
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| Involvement of capsaicin-sensitive sensory nerves in cardioprotection of rutaecarpine in rats. | Regulatory peptides 20030615 |
| The depressor and vasodilator effects of rutaecarpine are mediated by calcitonin gene-related peptide. | Planta medica 20030201 |
| Evodiamine, a constituent of Evodiae Fructus, induces anti-proliferating effects in tumor cells. | Cancer science 20030101 |
| Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice. | Life sciences 20020802 |
| The cardioprotection of rutaecarpine is mediated by endogenous calcitonin related-gene peptide through activation of vanilloid receptors in guinea-pig hearts. | Planta medica 20020801 |
| Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. | The Journal of biological chemistry 20020419 |
| The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. | Drug metabolism and disposition: the biological fate of chemicals 20020301 |
| Rutaecarpine-induced block of delayed rectifier K+ current in NG108-15 neuronal cells. | Neuropharmacology 20011201 |
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| Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa. | Life sciences 20011130 |
| Rutaecarpine, a quinazolinocarboline alkaloid, inhibits prostaglandin production in RAW264.7 macrophages. | Planta medica 20010801 |
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