444932-31-4

Basic information

• Product Name: TC-O 9311
• Synonyms: TC-O 9311;2-(3,5-diMethoxybenzoyl)-N-(naphthalen-1-yl)hydrazinecarboxaMide;1-[(3,5-dimethoxybenzoyl)amino]-3-naphthalen-1-ylurea
• CAS NO: 444932-31-4
• Molecular Formula: C₂₀H₁₉N₃O₄
• Molecular Weight: 365.38256
• Mol File: 444932-31-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TC-O 9311(CAS DataBase Reference)
• NIST Chemistry Reference: TC-O 9311(444932-31-4)
• EPA Substance Registry System: TC-O 9311(444932-31-4)

Safety Data

• Hazardous Substances Data: 444932-31-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TC-O 9311 is used as a pharmaceutical agent for its agonistic activity on the GPR139 receptor. Its activation of this receptor has been associated with potential therapeutic benefits in various conditions, making it a promising candidate for the development of new drugs.
Used in Neurological Applications:
In the field of neurology, TC-O 9311 is used as a research tool to study the role of GPR139 in the brain. Its agonistic effects on the receptor can provide insights into the receptor's function and help in understanding its potential involvement in neurological disorders.
Used in Drug Discovery and Development:
TC-O 9311 is used as a lead compound in drug discovery and development. Its potent agonistic activity on the GPR139 receptor makes it a valuable starting point for the design and synthesis of new drugs targeting this receptor for various therapeutic applications.
Used in Research and Development of Drug Delivery Systems:
Similar to gallotannin, TC-O 9311 can also be employed in the development of novel drug delivery systems to enhance its applications and efficacy. Various organic and metallic nanoparticles can be used as carriers for TC-O 9311 delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

Upstream product

• 51707-38-1 3,5-dimethoxy-benzoic acid hydrazide 
• 86-84-0 1-Naphthyl isocyanate 
• 263567-38-0 C₉H₁₁BrN₂O₃ 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 1279654-58-8 C₂₀H₁₈BrN₃O₄ 
• 56518-42-4 4-bromo-3,5-dimethoxybenzoic acid 
• 26050-64-6 methyl 4-bromo-3,5-dimethoxybenzoate 

Relevant articles and documents

Radiosynthesis and characterisation of a potent and selective GPR139 agonist radioligand

Compound 1 is a selective and potent agonist of the G protein-coupled receptor GPR139 (EC50 = 39 nM). In this study, we describe the synthesis, radiolabelling and in vitro evaluation of [3H]-1 for the characterisation of GPR139 and its spatial expression in the brain using autoradiography. Two different synthesis routes for the radiolabelling of 1 based on a reductive debromination strategy were investigated using deuterium (D2, g). The route based on reductive debromination of the bromonaphthyl precursor 5 proved superior over arylbromide 4 and was employed for the radiolabelling experiments. Reductive debromination of precursor 5 was accomplished using 3H2, Pd/C and triethylamine in DMF at ambient temperature to give target molecule [3H]-1 with a specific activity of 19.3 Ci mmol-1 and a radiochemical purity of ≥95%. By application of autoradiography and binding studies, it was not possible to discriminate [3H]-1 binding to wildtype mice brains from GPR139 knockout mice brains and total binding from non-specific binding in CHO-k1 cells stably expressing human GPR139 receptor. Based on these experiments we conclude that [3H]-1 is not a suitable radioligand for the characterisation of GPR139.

Discovery and SAR of a series of agonists at orphan G protein-coupled receptor 139

GPR139 is an orphan G-protein coupled receptor (GPCR) which is primarily expressed in the central nervous system (CNS). In order to explore the biological function of this receptor, selective tool compounds are required. A screening campaign identified compound 1a as a high potency GPR139 agonist with an EC50 = 39 nM in a calcium mobilization assay in CHO-K1 cells stably expressing the GPR139 receptor. In the absence of a known endogenous ligand, the maximum effect was set as 100% for 1a. Screening against 90 diverse targets revealed no cross-reactivity issues. Assessment of the pharmacokinetic properties showed limited utility as in vivo tool compound in rat with a poor whole brain exposure of 61 ng/g and a brain/plasma (b/p) ratio of 0.03. Attempts to identify a more suitable analogue identified the des-nitrogen analogue 1s with a reduced polar surface area of 76.7 A2 and an improved b/p ratio of 2.8. The whole brain exposure remained low at 95 ng/g due to a low plasma exposure.