51061-22-4

Usage

Uses

Used in Psychopharmacological Research:
3-Phenoxyphenethylamine is utilized as a research chemical in the field of psychopharmacology to study its psychoactive effects and mechanisms of action. Understanding its impact on the central nervous system can contribute to the development of new therapeutic agents for various neurological and psychiatric disorders.
Used in Recreational Drug Culture:
Although not recommended due to potential health risks and legal concerns, 3-Phenoxyphenethylamine has been used as a recreational drug for its psychedelic and hallucinogenic effects. Its use in this context provides insights into the effects of psychoactive substances on human perception and consciousness.

InChI:InChI=1/C15H17NO/c16-10-9-13-7-4-8-15(11-13)17-12-14-5-2-1-3-6-14/h1-8,11H,9-10,12,16H2

Upstream product

• 24550-32-1 1-(benzyloxy)-3-(2-nitrovinyl)benzene 
• 24550-32-1 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene 
• 100-44-7 benzyl chloride 
• 20967-96-8 2-(3-benzyloxyphenyl)acetonitrile 
• 14044-65-6 borane-THF 
• 198884-08-1 1-benzyloxy-3-(2-nitro-ethyl)-benzene 
• 100-39-0 benzyl bromide 
• 29973-97-5 2-(3-benzyloxyphenyl)ethyl amine hydrochloride 
• 100-83-4 meta-hydroxybenzaldehyde 
• 1700-37-4 3-Benzyloxybenzaldehyde 

Downstream Products

• 478855-44-6 N-[2-(3-benzyloxy-phenyl)-ethyl]-benzamide 
• 79641-67-1 phenyl-acetic acid-(3-benzyloxy-phenethylamide) 
• 261913-78-4 6-benzyloxy-1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 295320-31-9 2-(4-hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl}acetamide 
• 942302-64-9 [2-(3-benzyloxy-phenyl)-ethyl]-(cyclopropylmethyl)amine 
• 942302-66-1 [2-(3-benzyloxy-phenyl)-ethyl]-(furan-2-ylmethyl)amine 
• 942303-26-6 2-[2-(3-benzyloxy-phenyl)-ethylamino]-N,N-dimethyl-acetamide 
• 942303-52-8 [2-(3-benzyloxy-phenyl)-ethyl]-(tetrahydrofuran-3-yl)amine 
• 1233354-88-5 C₃₂H₃₂FNO₇S 
• 946136-65-8 C₂₁H₂₇NO*ClH 
• 1414380-10-1 ethyl [β-(3-benzyloxy)phenethylamino]-oxobutanoate 
• 1414380-17-8 C₂₀H₂₀N₂O₃ 
• 1414380-16-7 8-(4-fluorobenzyloxy)-1,2,3,5,6,10a-hexahydropyrrolo[2,1-a]isoquinolin-3-one 

Relevant academic research and scientific papers

NOVEL DIHYDROPYRIDOISOQUINOLINONES AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS

A compound according to Formula (I): wherein R1, LA, CyA, RA, R2, R3, and R4 are as described herein. The present invention relates to novel compounds according to Formula I that antagonize GPR84, a G-protein-coupled receptor that is involved in inflammatory conditions, and methods for the production of these novel compounds, pharmaceutical compositions comprising these compounds, and methods for the prevention and/or treatment of inflammatory conditions, pain, neuroinflammatory conditions, neurodegenerative conditions, infectious diseases, autoimmune diseases, endocrine and/or metabolic diseases, cardiovascular diseases, leukemia, and/or diseases involving impairment of immune cell functions by administering a compound of the invention.

The importance of the 6- and 7-positions of tetrahydroisoquinolines as selective antagonists for the orexin 1 receptor

Selective antagonism of the orexin 1 (OX1) receptor has been proposed as a potential mechanism for treatment of drug addiction. We have previously reported studies on the structure-activity relationships of tetrahydroisoquinoline-based antagonists. In this report, we elucidated the respective role of the 6- and 7-substitutions by preparation of a series of either 6-substituted tetrahydroisoquinolines (with no 7-substituents) or vice versa. We found that 7-substituted tetrahydroisoquinolines showed potent antagonism of OX1, indicating that the 7-position is important for OX1 antagonism (10c, Ke = 23.7 nM). While the 6-substituted analogs were generally inactive, several 6-amino compounds bearing ester groups showed reasonable potency (26a, Ke = 427 nM). Further, we show evidence that suggests several compounds initially displaying insurmountable antagonism at the OX1 receptor are competitive antagonists with slow dissociation rates.

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

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.

NOVEL DIHYDROPYRIDOISOQUINOLINONES AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS

A compound according to Formula I: wherein R1, LA, GA, R2a, R2b, R3, R4, R5, and R6 are as described herein. The present invention relates to novel compound

Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones

The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3- ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a] isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively.

Macrocyclic BACE inhibitors: Optimization of a micromolar hit to nanomolar leads

We have identified macrocyclic inhibitors of the aspartic protease BACE, implicated in the etiology of Alzheimer's disease. An X-ray structure of screening hit 1 in the BACE active site revealed a hairpin conformation suggesting that constrained macrocycl

Synthesis and biological evaluation of berberine analogues as novel up-regulators for both low-density-lipoprotein receptor and insulin receptor

Berberine (BBR) is a natural compound with up-regulating activity on both low-density-lipoprotein receptor (LDLR) and insulin receptor (InsR). This one-drug-multiple-target characteristic might be suitable for the treatment of metabolic syndrome. In searching for up-regulators effective for both LDLR and InsR expression, the structure-activity relationship (SAR) analysis for BBR analogues was done. Fourteen BBR analogues were designed, synthesized and biologically evaluated. SAR analysis revealed that appropriate modifications on the phenyl ring A or D of BBR might retain the up-regulatory activities on the expression of both LDLR and InsR. Among these compounds, compound 13a bearing 9-methoxy and 10-hydroxyl on the ring D showed promising activities on either LDLR or InsR gene expression. The 10-hydroxyl of 13a could be an arm to connect proper chemical groups for optimizing drug-bioavailability in vivo. Thus, 13a could be considered to be a parent compound to make pro-drugs for either blood lipids or glucose.

MACROCYCLE DERIVATIVES USEFUL AS INHIBITORS OF beta-SECRETASE (BACE)

The present invention is directed to macrocycle derivatives, pharmaceutical compositions containing them and their use in the treatment of Alzheimer's disease (AD) and related disorders. The compounds of the invention are inhibitors of β-secretase, also known as β-site cleaving enzyme and BACE, BACE1, Asp2 and memapsin2.

Compounds and methods for modulation of estrogen receptors

Compounds that modulate the estrogen receptor (ER) are disclosed, as well as pharmaceutical compositions containing the same. In a specific embodiment, the compounds are selective for ER-β over ER-α. Methods are disclosed for modulating ER-β in cell and/o

Syntheses and antitumor targeting G1 phase of the cell cycle of benzoyldihydroisoquinolines and related 1-substituted isoquinolines

A series of 1-substituted 3,4-dihydroisoquinolines were synthesized and tested in vitro against the leukemia L 1210 cell line to evaluate their ability to perturb the cell cycle by arresting cells in the G1 phase. 1-Benzoylimines, 1-phenylimines, and 1-alkylimines were synthesized. The most powerful cytotoxic derivatives, 1-benzoyl-3,4-dihydroisoquinolines (1-26), were obtained from amides I via 1-benzyl-3,4-dihydroisoquinoline in good yield by a direct selective oxidation of the benzylic carbon of the corresponding imines through 10% Pd/C in acetonitrile. SAR studies let us to identify the essential structural features for cytotoxic activity. The most bioactive compounds (with IC50 5μM) were BzDHIQ (13, 22, 21, 8, 9, 11, 1, 20, 6, and 19), and they are characterized by the following: (i) An α-ketoimine moiety is necessary for potent antiproliferative activity (1-phenyl- and 1-alkyl-3,4-dihydroisoquinoline derivatives, 34-40, are less active). (ii) An hydrophobic, benzyloxy, alkyloxy, or allyloxy group at the C-6 position seems to be relevant for cytotoxicity. (iii) Regarding the influence of the benzoylic moiety, both the unsubstituted (13, 8, 9, 11, 1, and 6) and the 3′-monosubstituted (22, 21, 20, and 19) compounds were more potent than compounds with other substitutions.