Talnetant

Base Information

• Chemical Name: Talnetant
• CAS No.: 174636-32-9
• Molecular Formula: C25H22 N2 O2
• Molecular Weight: 382.462
• European Community (EC) Number: 808-582-5
• UNII: CZ3T9T146K
• DSSTox Substance ID: DTXSID00870124
• Nikkaji Number: J750.057B
• Wikipedia: Talnetant
• Wikidata: Q76296793
• NCI Thesaurus Code: C76464
• Pharos Ligand ID: WM34S4ZTUHBP
• ChEMBL ID: CHEMBL10188
• Mol file: 174636-32-9.mol

Synonyms:N-(alpha-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide;SB 223412;SB-223412;Talnetant

Chemical Property of Talnetant

Chemical Property:

• Vapor Pressure: 4.51E-14mmHg at 25°C
• Melting Point: 125.1-126.2℃
• Boiling Point: 580.4°Cat760mmHg
• PKA: 6.70±0.50(Predicted)
• Flash Point: 304.8°C
• PSA: 65.71000
• Density: 1.212g/cm³
• LogP: 6.06330
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble25mg/mL, clear
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 382.168127949
• Heavy Atom Count: 29
• Complexity: 527

Purity/Quality:

99.1%, ^*data from raw suppliers

Talnetant ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC=CC=C1)NC(=O)C2=C(C(=NC3=CC=CC=C32)C4=CC=CC=C4)O
• Isomeric SMILES: CC[C@@H](C1=CC=CC=C1)NC(=O)C2=C(C(=NC3=CC=CC=C32)C4=CC=CC=C4)O
• Recent ClinicalTrials: Schizophrenia Study In Adults
• Recent EU Clinical Trials: An Eight-Week, Randomized, Double-Blind, Placebo-Controlled, Dose-Ranging Study to Evaluate Efficacy and Safety of Talnetant in Subjects with Irritable Bowel Syndrome
• Description: Talnetant is an antagonist of the neurokinin-3 (NK3) receptor (Ki = 1 nM). It is selective for NK3 over NK1 and NK2 receptors (Kis = 144 and >100,000 nM, respectively, in CHO cells expressing recombinant human receptors). Talnetant inhibits calcium mobilization induced by neurokinin B in HEK293 cells expressing human NK3 receptors (IC50 = 16.6 nM). It inhibits contractions induced by the NK3 receptor agonist senktide in isolated rabbit iris sphincter muscle (pD2 = 9.1). Talnetant (5-20 mg/kg) reduces senktide-induced head shakes and tail whips in mice. It also inhibits senktide-induced wet-dog shakes, increases extracellular dopamine and norepinephrine in the medial prefrontal cortex, and attenuates haloperidol-induced increases in nucleus accumbens dopamine levels in guinea pigs.

Technology Process of Talnetant

There total 11 articles about Talnetant which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

oxycinchophen (485-89-2) + (R)-1-phenylpropylamine (3789-59-1) → talnetant (174636-32-9,174636-26-1)

Guidance literature:

oxycinchophen; With 1,1'-carbonyldiimidazole; at 50 ℃; for 5h;

(R)-1-phenylpropylamine; at 25 - 70 ℃; for 17h;

DOI:10.1021/ol100453x

Reference yield: 83.0%

→ talnetant (174636-32-9,174636-26-1)

Guidance literature:

In 1-Propyl acetate; at -2 - 107 ℃; Purification / work up;

Reference yield: 80.0%

6,14,22,30-Tetraphenyl-[1,5,9,13]-tetraoxadecino[2,3-c:6,7-c':10,11c'':14,15-c''']tetraquinoline-8,16,24,32-tetrone + Ethyl 3-acetoxy-2-phenylquinoline-4-carboxylate + (R)-1-phenylpropylamine (3789-59-1) → talnetant (174636-32-9,174636-26-1)

Guidance literature:

In ethyl acetate; at 65 - 70 ℃; for 3h;

upstream raw materials:

oxycinchophen

(R)-1-phenylpropylamine

methoxymethyl phenyl ketone

3-methoxy-2-phenylquinoline-4-carboxylic cid

Downstream raw materials:

(S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamide

(S)-N-(α-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide

Refernces

• 1、 Rohbogner, Christoph J.,Wirth, Stefan,Knochel, Paul. "Phosphorodiamidate-directed metalation of N -heterocycles using Mg- and Zn-TMP bases". supporting information; scheme or table. p. 1984 - 1987. Retrieved 2010/07/15.
• 2、 -. "METHOD FOR THE SYNTHESIS OF QUINOLIΝE DERIVATIVES". Page/Page column 24-25. . Retrieved 2008/06/13.