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76-66-4,MFCD00221748
Catalog No.:AA00ICLW

76-66-4 | Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid,6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-a-(methoxymethylene)-2-oxo-,methyl ester, (aE,1'R,6'R,7'S,8'aS)-

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1mg
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5mg
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10mg
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20mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00ICLW
Chemical Name:
Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid,6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-a-(methoxymethylene)-2-oxo-,methyl ester, (aE,1'R,6'R,7'S,8'aS)-
CAS Number:
76-66-4
Molecular Formula:
C22H28N2O4
Molecular Weight:
384.4687
MDL Number:
MFCD00221748
SMILES:
COC=C(C1CC2N(CC1CC)CCC12C(=O)Nc2c1cccc2)C(=O)OC
Properties
Computed Properties
 
Complexity:
663  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
2.3  

Literature

Title: Rhynchophylline prevents cardiac dysfunction and improves survival in lipopolysaccharide-challenged mice via suppressing macrophage I-κBα phosphorylation.

Journal: International immunopharmacology 20121101

Title: Rhynchophylline attenuates LPS-induced pro-inflammatory responses through down-regulation of MAPK/NF-κB signaling pathways in primary microglia.

Journal: Phytotherapy research : PTR 20121001

Title: Isorhynchophylline: A plant alkaloid with therapeutic potential for cardiovascular and central nervous system diseases.

Journal: Fitoterapia 20120601

Title: Protective effect of isorhynchophylline against β-amyloid-induced neurotoxicity in PC12 cells.

Journal: Cellular and molecular neurobiology 20120401

Title: Isorhynchophylline, a natural alkaloid, promotes the degradation of alpha-synuclein in neuronal cells via inducing autophagy.

Journal: Autophagy 20120101

Title: Macrophyllionium and macrophyllines A and B, oxindole alkaloids from Uncaria macrophylla.

Journal: Journal of natural products 20110128

Title: Antihypertensive and neuroprotective activities of rhynchophylline: the role of rhynchophylline in neurotransmission and ion channel activity.

Journal: Journal of ethnopharmacology 20101028

Title: Effect of rhynchophylline on central neurotransmitter levels in amphetamine-induced conditioned place preference rat brain.

Journal: Fitoterapia 20101001

Title: Effects of rhynchophylline and isorhynchophylline on nitric oxide and endothelin-1 secretion from RIMECs induced by Listeriolysin O in vitro.

Journal: Veterinary microbiology 20100714

Title: Rhynchophylline down-regulates NR2B expression in cortex and hippocampal CA1 area of amphetamine-induced conditioned place preference rat.

Journal: Archives of pharmacal research 20100401

Title: Metabolism and pharmacokinetics of rhynchophylline in rats.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Metabolism of isorhynchophylline in rats detected by LC-MS.

Journal: Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20100101

Title: [Effect of major components of maijunan tablets on the transport of hydrochlorothiazide in Caco-2 cell monolayer model].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100101

Title: Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism.

Journal: International immunopharmacology 20091201

Title: [HPLC determination of rhynchophylline and isorhynchophylline in Anshen Yangxue oral liquid].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090701

Title: Rhynchophylline from Uncaria rhynchophylla functionally turns delayed rectifiers into A-Type K+ channels.

Journal: Journal of natural products 20090522

Title: Uncaria rhynchophylla and Rhynchophylline inhibit c-Jun N-terminal kinase phosphorylation and nuclear factor-kappaB activity in kainic acid-treated rats.

Journal: The American journal of Chinese medicine 20090101

Title: Effects of isorhynchophylline on angiotensin II-induced proliferation in rat vascular smooth muscle cells.

Journal: The Journal of pharmacy and pharmacology 20081201

Title: Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia.

Journal: Journal of natural products 20080701

Title: General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.

Journal: The Journal of organic chemistry 20060818

Title: Inhibitory effect of rhynchophylline on human ether-a-go-go related gene channel.

Journal: Sheng li xue bao : [Acta physiologica Sinica] 20051025

Title: Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies.

Journal: European journal of pharmacology 20050711

Title: Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action.

Journal: Life sciences 20041203

Title: In vitro vasodilator mechanisms of the indole alkaloids rhynchophylline and isorhynchophylline, isolated from the hook of Uncaria rhynchophylla (Miquel).

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20040201

Title: Pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline.

Journal: Acta pharmacologica Sinica 20030201

Title: Rhynchophylline and isorhynchophylline inhibit NMDA receptors expressed in Xenopus oocytes.

Journal: European journal of pharmacology 20021122

Title: Effect of rhynchophylline on apoptosis induced by dopamine in NT2 cells.

Journal: Acta pharmacologica Sinica 20020501

Title: Dan Yuan, et al. Anti-inflammatory effects of rhynchophylline and isorhynchophylline in mouse N9 microglial cells and the molecular mechanism. International ImmunopharmacologyVolume 9, Issues 13–14, December 2009, Pages 1549–1554

Title: Houcai Huang, et al. Neuroprotective Effects of Rhynchophylline Against Ischemic Brain Injury via Regulation of the Akt/mTOR and TLRs Signaling Pathways. Molecules 2014, 19 (8): 11196-11210; doi:10.3390/molecules190811196

Title: Tai-Hyun Kang, et al. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life SciencesVolume 76, Issue 3, 3 December 2004, Pages 331–343

Title: Kinzo Matsumoto, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: Behavioural and electrophysiological studies. European Journal of PharmacologyVolume 517, Issue 3, 11 July 2005, Pages 191–199

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Tags:76-66-4 Molecular Formula|76-66-4 MDL|76-66-4 SMILES|76-66-4 Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid,6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-a-(methoxymethylene)-2-oxo-,methyl ester, (aE,1'R,6'R,7'S,8'aS)-