Home Indole and Oxindoles 68573-23-9
68573-23-9,MFCD28125425
Catalog No.:AA005P8A

68573-23-9 | N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enamide

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1mg
99%
1 week  
$336.00   $235.00
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5mg
99%
1 week  
$685.00   $480.00
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10mg
99%
1 week  
$1,035.00   $724.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA005P8A
Chemical Name:
N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enamide
CAS Number:
68573-23-9
Molecular Formula:
C20H20N2O4
Molecular Weight:
352.3838
MDL Number:
MFCD28125425
SMILES:
COc1cc(C=CC(=O)NCCc2c[nH]c3c2cc(O)cc3)ccc1O
NSC Number:
369502
Properties
Properties
 
Form:
Solid  
MP:
115-118°C  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
498  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
6  
XLogP3:
3  

Downstream Synthesis Route

[1]Somei,Masanori;Morikawa,Harunobu;Yamada,Koji;Yamada,Fumio[Heterocycles,1998,vol.48,#6,p.1117-1120]

[2]Takao,Koichi;Toda,Kazuhiro;Saito,Takayuki;Sugita,Yoshiaki[ChemicalandPharmaceuticalBulletin,2017,vol.65,#11,p.1020-1027]

[3]Tanaka,Eiji;Tanaka,Chihiro;Mori,Naoki;Kuwahara,Yasumasa;Tsuda,Mitsuya[Phytochemistry,2003,vol.64,#5,p.965-969]

[1]Takahashi,Toshiyuki;Miyazawa,Mitsuo[BioorganicandMedicinalChemistryLetters,2011,vol.21,#7,p.1983-1986]

[2]Locationinpatent:experimentalpartTakahashi;Miyazawa,Mitsuo[Pharmazie,2011,vol.66,#4,p.301-305]

[3]Takahashi,Toshiyuki;Miyazawa,Mitsuo[MedicinalChemistryResearch,2012,vol.21,#8,p.1762-1770]

[4]Hu,Weimin;Qin,Hua;Cui,Yuxin;Jia,Yanxing[Chemistry-AEuropeanJournal,2013,vol.19,#9,p.3139-3147]

Literature

Title: N-Caffeoyl serotonin as selective COX-2 inhibitor.

Journal: Bioorganic & medicinal chemistry letters 20120401

Title: Synthesis, biological activities and bioavailability of moschamine, a safflomide-type phenylpropenoic acid amide found in Centaurea cyanus.

Journal: Natural product research 20120101

Title: Effect of N-(p-coumaroyl)serotonin and N-feruloylserotonin, major anti-atherogenic polyphenols in safflower seed, on vasodilation, proliferation and migration of vascular smooth muscle cells.

Journal: Molecular nutrition & food research 20111001

Title: Methanol elicits the biosynthesis of 4-coumaroylserotonin and feruloylserotonin in rice seedlings.

Journal: Plant signaling & behavior 20110601

Title: Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition.

Journal: Bioorganic & medicinal chemistry letters 20110401

Title: Naturally appearing N-feruloylserotonin isomers suppress oxidative burst of human neutrophils at the protein kinase C level.

Journal: Pharmacological reports : PR 20110101

Title: Protective effect of serotonin derivatives on glucose-induced damage in PC12 rat pheochromocytoma cells.

Journal: The British journal of nutrition 20100101

Title: Suppression of oxidative burst in human neutrophils with the naturally occurring serotonin derivative isomer from Leuzea carthamoides.

Journal: Neuro endocrinology letters 20100101

Title: Safflower seed polyphenols (N-(p-coumaroyl)serotonin and N-feruloylserotonin) ameliorate atherosclerosis and distensibility of the aortic wall in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits.

Journal: Hypertension research : official journal of the Japanese Society of Hypertension 20091101

Title: N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells.

Journal: Bioorganic & medicinal chemistry letters 20090801

Title: Inhibitory effect of serotonin derivatives on high glucose-induced adhesion and migration of monocytes on human aortic endothelial cells.

Journal: The British journal of nutrition 20090701

Title: The selective effect of N-feruloylserotonins isolated from Leuzea carthamoides on nociception and anxiety in rats.

Journal: Journal of ethnopharmacology 20070613

Title: Serotonin derivatives, major safflower (Carthamus tinctorius L.) seed antioxidants, inhibit low-density lipoprotein (LDL) oxidation and atherosclerosis in apolipoprotein E-deficient mice.

Journal: Journal of agricultural and food chemistry 20060712

Title: Shin-ichiro Katsuda, et al. Safflower Seed Polyphenols (N-(p-coumaroyl)serotonin and N-feruloylserotonin) Ameliorate Atherosclerosis and Distensibility of the Aortic Wall in Kurosawa and Kusanagi-hypercholesterolemic (KHC) Rabbits. Hypertens Res. 2009 Nov;32(11):944-9.

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Tags:68573-23-9 Molecular Formula|68573-23-9 MDL|68573-23-9 SMILES|68573-23-9 N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enamide