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Cas Database

3937-16-4

3937-16-4

Identification

  • Product Name:Benzeneethanamine,2,3,4-trimethoxy-

  • CAS Number: 3937-16-4

  • EINECS:

  • Molecular Weight:211.261

  • Molecular Formula: C11H17 N O3

  • HS Code:2922299090

  • Mol File:3937-16-4.mol

Synonyms:Phenethylamine,2,3,4-trimethoxy- (7CI,8CI); 2,3,4-Trimethoxy-b-phenethylamine; 2,3,4-Trimethoxybenzeneethanamine;2,3,4-Trimethoxyphenethylamine; 2,3,4-Trimethoxyphenylethylamine;2-(2,3,4-Trimethoxyphenyl)ethylamine

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  • Manufacture/Brand:TRC
  • Product Description:2-(2,3,4-trimethoxyphenyl)ethan-1-amine
  • Packaging:250mg
  • Price:$ 330
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  • Manufacture/Brand:Labseeker
  • Product Description:2-(2,3,4-trimethoxyphenyl)ethanamine 95
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:2-(2,3,4-TRIMETHOXYPHENYL)ETHANAMINE 95.00%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:2-(2,3,4-TRIMETHOXYPHENYL)ETHANAMINE 95.00%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:2-(2,3,4-TRIMETHOXYPHENYL)ETHANAMINE 95.00%
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  • Manufacture/Brand:AK Scientific
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Relevant articles and documentsAll total 15 Articles be found

Synthesis, binding, and functional properties of tetrahydroisoquinolino-2-alkyl phenones as selective σ2R/TMEM97 ligands

Xie, Xiao-Yang,Li, Yu-Yun,Ma, Wen-Hui,Chen, Ai-Fang,Sun, Yu-Tong,Lee, Ji Youn,Riad, Aladdin,Xu, Dao-Hua,Mach, Robert H.,Huang, Yun-Sheng

, (2021)

Sigma-2 receptor (σ2R/TMEM97) has been implicated to play important roles in multiple cellular dysfunctions, such as cell neoplastic proliferation, neuro-inflammation, neurodegeneration, etc. Selective σ2 ligands are believed to be promising pharmacological tools to regulate or diagnose various disorders. As an ongoing effort of discovery of new and selective σ2 ligands, we have synthesized a series of tetrahydroisoquinolino-2-alkyl phenone analogs and identified that 10 of them have moderate to potent affinity and selectivity for σ2R/TMEM97. Especially, 4 analogs showed Ki values ranging from 0.38 to 5.1 nM for σ2R/TMEM97 with no or low affinity for sigma-1 receptor (σ1R). Functional assays indicated that these 4 most potent analogs had no effects on intracellular calcium concentration and were classified as putative σ2R/TMEM97 antagonists according to current understanding. The σ2R/TMEM97 has been suggested to play important roles in the central nervous system. Based on published pharmacological and clinical results from several regarded σ2R/TMEM97 antagonists, these analogs may potentially be useful for the treatment of various neurodegenerative diseases.

Seiler et al.

, p. 306 (1965)

Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents

Fan, Tian-Yun,Yang, Yu-Xin,Zeng, Qing-Xuan,Wang, Xue-Lei,Wei, Wei,Guo, Xi-Xi,Zhao, Li-Ping,Song, Dan-Qing,Wang, Yan-Xiang,Wang, Li,Hong, Bin

, (2021/06/01)

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhanced the survival rate of patient with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives were synthesized and evaluated for their activities on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure–activity relationship (SAR) analysis revealed that 2,3-dimethoxy moiety might be beneficial for activity. Among them, 9k displayed the most potent activity with IC50 value of 9.5 ± 0.5 μM, better than that of BBR. Also, it significantly decreased PCSK9 protein level at cellular level, as well as in the liver and serum of mice in vivo. Furthermore, 9k markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of 9k is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, 9k might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet-Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

Bartel, Karin,Bracher, Franz,Geisslinger, Franz,Keller, Marco,Sauvageot-Witzku, Karl,Schaefer, Michael,Urban, Nicole

supporting information, p. 2716 - 2725 (2022/01/12)

We present a systematic investigation on an improved variant of the N-acyl-Pictet-Spengler condensation for the synthesis of 1-benzyltetrahydroisoquinolines, based on our recently published synthesis of N-methylcoclaurine, exemplified by the total syntheses of 10 alkaloids in racemic form. Major advantages are a) using ω-methoxystyrenes as convenient alternatives to arylacetaldehydes, and b) using the ethoxycarbonyl residue for both activating the arylethylamine precursors for the cyclization reaction, and, as a significant extension, also as protective group for phenolic residues. After ring closure, the ethoxycarbonyl-protected phenols are deprotected simultaneously with the further processing of the carbamate group, either following route A (lithium alanate reduction) to give N-methylated phenolic products, or following route B (treatment with excess methyllithium) to give the corresponding alkaloids with free N-H function. This dual use of the ethoxycarbonyl group shortens the synthetic routes to hydroxylated 1-benzyltetrahydroisoquinolines significantly. Not surprisingly, these ten alkaloids did not show noteworthy effects on TPC2 cation channels and the tumor cell line VCR-R CEM, and did not exhibit P-glycoprotein blocking activity. But due to their free phenolic groups they can serve as valuable intermediates for novel derivatives addressing all of these targets, based on previous evidence for structure-activity relationships in this chemotype.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Zheng, Bo,Qu, Hui-Ya,Meng, Tian-Zhuo,Lu, Xia,Zheng, Jie,He, Yun-Gang,Fan, Qi-Qi,Shi, Xiao-Xin

, p. 28997 - 29007 (2018/08/29)

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Tangdenpaisal, Kassrin,Worayuthakarn, Rattana,Karnkla, Supatra,Ploypradith, Poonsakdi,Intachote, Pakamas,Sengsai, Suchada,Saimanee, Busakorn,Ruchirawat, Somsak,Chittchang, Montakarn

, p. 925 - 937 (2015/03/31)

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Process route upstream and downstream products

Process route

1,2,3-trimethoxy-4-(2-nitro-vinyl)benzene
4668-08-0

1,2,3-trimethoxy-4-(2-nitro-vinyl)benzene

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
1,2,3-trimethoxy-4-(2-nitro-vinyl)benzene; With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating / reflux;
With hydrogenchloride; In tetrahydrofuran; water; ethyl acetate;
With ammonia; tartaric acid; more than 3 stages;
84%
With lithium aluminium tetrahydride;
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 80 ℃; for 12h;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 1 h / 20 °C / Cooling with ice
2: 5%-palladium/activated carbon; ammonium formate / ethanol / 2 h / Reflux
With sodium tetrahydroborate; 5%-palladium/activated carbon; ammonium formate; In ethanol;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / 2 h / Reflux
2: zinc; hydrogenchloride / ethanol; water / 3 h
With hydrogenchloride; methanol; sodium tetrahydroborate; zinc; In ethanol; water;
(E)-1-nitro-2-(2',3',4'-trimethoxyphenyl)ethene
118474-94-5

(E)-1-nitro-2-(2',3',4'-trimethoxyphenyl)ethene

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
With lithium borohydride; chloro-trimethyl-silane; In tetrahydrofuran; for 24h; Ambient temperature;
91%
With sulfuric acid; hydrogen; acetic acid; palladium(IV) oxide; under 760 Torr;
91%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 24h;
83%
With lithium aluminium tetrahydride; In tetrahydrofuran; Reflux;
82%
With lithium aluminium tetrahydride; In tetrahydrofuran;
72%
With hydrogenchloride; zinc; In ethanol; water; at 0 ℃; for 4.5h;
9.5%
With hydrogenchloride; ethanol; acetic acid; Reduktion an Blei-Kathoden;
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 65 ℃; Inert atmosphere;
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 75 ℃; for 1.5h; Inert atmosphere;
(Z)-1,2,3-trimethoxy-4-(2-nitrovinyl)benzene
1428796-91-1

(Z)-1,2,3-trimethoxy-4-(2-nitrovinyl)benzene

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 3h; Inert atmosphere; Reflux;
7.7 g
1,2,3-trimethoxy-4-(2-nitroethyl)benzene

1,2,3-trimethoxy-4-(2-nitroethyl)benzene

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
With 5%-palladium/activated carbon; ammonium formate; In ethanol; for 2h; Reflux;
With hydrogenchloride; zinc; In ethanol; water; for 3h;
C<sub>21</sub>H<sub>21</sub>N<sub>3</sub>O<sub>4</sub>
291301-33-2

C21H21N3O4

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In ethanol; for 24h;
82%
C<sub>11</sub>H<sub>15</sub>NO<sub>6</sub>
1111086-84-0

C11H15NO6

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
With lithium aluminium tetrahydride;
3-(2,3,4-trimethoxy-phenyl)-propionic acid amide
857813-99-1

3-(2,3,4-trimethoxy-phenyl)-propionic acid amide

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
With alkaline aqueous sodium hypobromite;
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: AlCl3; HCl; benzene / anschliessend Erhitzen mit Wasser
2: piperidine; pyridine
3: aq. NaOH solution; sodium-amalgam
4: thionyl chloride; chloroform / anschliessendes Behandeln mit einer wss. Loesung von Natriumhydroxid und Ammoniak
5: alkaline aqueous sodium hypobromite
With piperidine; pyridine; hydrogenchloride; sodium hydroxide; sodium amalgam; aluminium trichloride; thionyl chloride; chloroform; alkaline aqueous sodium hypobromite; benzene;
3-(2,3,4-trimethoxy-phenyl)-propionic acid
33130-04-0

3-(2,3,4-trimethoxy-phenyl)-propionic acid

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: thionyl chloride; chloroform / anschliessendes Behandeln mit einer wss. Loesung von Natriumhydroxid und Ammoniak
2: alkaline aqueous sodium hypobromite
With thionyl chloride; chloroform; alkaline aqueous sodium hypobromite;
trans-2,3,4-trimethoxycinnamic acid
116406-19-0

trans-2,3,4-trimethoxycinnamic acid

2-(2,3,4-trimethoxyphenyl)ethylamine
3937-16-4

2-(2,3,4-trimethoxyphenyl)ethylamine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: aq. NaOH solution; sodium-amalgam
2: thionyl chloride; chloroform / anschliessendes Behandeln mit einer wss. Loesung von Natriumhydroxid und Ammoniak
3: alkaline aqueous sodium hypobromite
With sodium hydroxide; sodium amalgam; thionyl chloride; chloroform; alkaline aqueous sodium hypobromite;

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