134865-74-0

Basic information

• Product Name: 4-P-PDOT
• Synonyms: 4-PHENYL-2-PROPIONAMIDOTETRALIN;4-P-PDOT;N-(4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanamide
• CAS NO: 134865-74-0
• Molecular Formula: C19H21NO
• Molecular Weight: 279.38
• Product Categories: Melatonin receptor
• Mol File: 134865-74-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 166 °C
• Boiling Point: 480.1°Cat760mmHg
• Flash Point: 292°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 2.22E-09mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Store at RT
• PKA: 15.87±0.40(Predicted)
• CAS DataBase Reference: 4-P-PDOT(CAS DataBase Reference)
• NIST Chemistry Reference: 4-P-PDOT(134865-74-0)
• EPA Substance Registry System: 4-P-PDOT(134865-74-0)

Safety Data

• RTECS: TX1498350
• Hazardous Substances Data: 134865-74-0(Hazardous Substances Data)

Usage

Uses

4-P-PDOT is a MT2 melatonin receptor ligand.

Biological Activity

Melatonin receptor antagonist, >300-fold selective for the MT 2 (vs MT 1 ) subtype.

Biochem/physiol Actions

4-P-PDOT is a slelctive MT2 melatonin receptor antagonist 300 fold selective for MT2 (MEL-1B-R) vs MT1 (MEL-1A-R) melatonin receptor subtype.

InChI:InChI=1/C19H21NO/c1-2-19(21)20-16-12-15-10-6-7-11-17(15)18(13-16)14-8-4-3-5-9-14/h3-11,16,18H,2,12-13H2,1H3,(H,20,21)

Upstream product

• 299422-50-7 4-phenyl-2-(2'-bromopropenoylamido)tetralin 
• 123-62-6 propionic acid anhydride 
• 100-52-7 benzaldehyde 
• 1187323-15-4 (+)-(2R,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalene-2-ol 
• 1353637-92-9 (-)-(2R,4R)-4-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl methanesulfonate 
• 1254802-65-7 (-)-(2S,4R)-2-azido-4-phenyl-1,2,3,4-tetrahydronaphthalene 
• 1353637-95-2 2-methyl-N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propane-2-sulfinamide 
• 1353637-93-0 (+)-(R)-4-phenyl-3,4-dihydronaphthalen-2(1H)-one 
• 150402-73-6 4-phenyl-2-tetralone 
• 1353637-94-1 (R)-N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propionamide 
• 1353637-88-3 (S)-N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propionamide 
• 1353637-89-4 2-methyl-N-(4-phenyl-3,4-dihydronaphthalen-2-yl)propane-2-sulfinamide 
• 1353637-87-2 (-)-(S)-4-phenyl-3,4-dihydronaphthalen-2(1H)-one 
• 1254802-74-8 (-)-(2S,4S)-4-phenyl-1,2,3,4-tetrahydronaphthalene-2-ol 

Relevant articles and documents

Conformation by NMR of two tetralin-based receptor ligands

The conformation in solution of 1-phenyl-3-propionamido-1,2,3,4-tetrahydronaphthalene and 1-phenyl-3-(N,N-dimethylamino)-1,2,3,4-tetrahydronaphthalene has been determined by a combination of nuclear magnetic resonance measurements and molecular mechanics

Toward the definition of stereochemical requirements for MT 2-selective antagonists and partial agonists by studying 4-phenyl-2-propionamidotetralin derivatives

New derivatives of 4-phenyl-2-propionamidotetralin (4-P-PDOT) were prepared and tested on cloned MT1 and MT2 receptors, with the purpose of merging previously reported pharmacophores for nonselective agonists and for MT2-selective antagonists. A 8-methoxy group increases binding affinity of both (±)-cis- and (±)-trans-4-P-PDOT, and it can be bioisosterically replaced by a bromine. Conformational analysis of 8-methoxy-4-P-PDOT by molecular dynamics, supported by NMR data, revealed an energetically favored conformation for the (2S,4S)-cis isomer and a less favorable conformation for the (2R,4S)-trans one, fulfilling the requirements of a pharmacophore model for nonselective melatonin receptor agonists. A new superposition model, including features characteristic of MT2- selective antagonists, suggests that MT1/MT2 agonists and MT2 antagonists can share the same arrangement for their pharmacophoric elements. The model correctly predicted the eutomers of (±)-cis- and (±)-trans-4-P-PDOT. The model was validated by preparing three dihydronaphthalene derivatives, either able or not able to reproduce the putative active conformation of 4-P-PDOT. (Figure presented)

An improved synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT): A selective MT2 melatonin receptor antagonist

A novel, efficient and diastereoselective procedure was developed for the gram-scale synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT), a selective MT2 melatonin receptor antagonist. The synthetic strategy involved the conversion of 4