174635-69-9

Basic information

• Product Name: SB 222200
• Synonyms: (S)-3-METHYL-2-PHENYL-N-(1-PHENYLPROPYL)-4-QUINOLINECARBOXAMIDE;SB 222200;3-METHYL-2-PHENYL-N-[(1S)-1-PHENYLPROPYL]-4-QUINOLINECARBOXAMIDE;3-Methyl-2-phenyl-N-((1S)-1-phenylpropyl)quinoline-4-carboxamide;SB222200//3-Methyl-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxaMide
• CAS NO: 174635-69-9
• Molecular Formula: C26H24N2O
• Molecular Weight: 380.48
• Mol File: 174635-69-9.mol

Chemical Properties

• Melting Point: 154℃
• Boiling Point: 553.5°Cat760mmHg
• Flash Point: 288.6°C
• Appearance: light yellow/solid
• Density: 1.142
• Vapor Pressure: 2.7E-12mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: 2-8°C
• Solubility: DMSO: ~28 mg/mL, soluble
• PKA: 12.88±0.46(Predicted)
• CAS DataBase Reference: SB 222200(CAS DataBase Reference)
• NIST Chemistry Reference: SB 222200(174635-69-9)
• EPA Substance Registry System: SB 222200(174635-69-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 174635-69-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
SB 222200 is used as an antagonist for the NK3 receptor, which plays a significant role in various physiological processes. Its application in this industry is primarily for the development of antipsychotic medications, targeting the treatment of psychiatric disorders.
Used in Research and Development:
In the field of research and development, SB 222200 serves as a valuable tool for studying the functions and interactions of the NK3 receptor. This understanding can lead to the discovery of new therapeutic approaches and the development of novel antipsychotic drugs.
Used in Preparation of Acylpiperazinyl-Pyrazoles:
SB 222200 is also used in the preparation of acylpiperazinyl-pyrazoles, a class of compounds with potential applications in the treatment of various psychiatric conditions. The development of these compounds can contribute to the advancement of antipsychotic medications and improve patient outcomes.

Biological Activity

Potent and selective non-peptide NK 3 receptor antagonist. K i values are 4.4, >100,000 and 250 nM for human NK 3 , NK 1 and NK 2 receptors respectively. Brain penetrant and active in vivo .

InChI:InChI=1/C26H24N2O/c1-3-22(19-12-6-4-7-13-19)28-26(29)24-18(2)25(20-14-8-5-9-15-20)27-23-17-11-10-16-21(23)24/h4-17,22H,3H2,1-2H3,(H,28,29)/t22-/m0/s1

Upstream product

• 43071-45-0 3-methyl-2-phenylquinoline-4-carboxylic acid 
• 3789-59-1 (R)-1-phenylpropylamine 
• 174636-71-6 3-methyl-2-phenylquinoline-4-carbonyl chloride 
• 661-69-8 hexamethyldistannane 
• 174636-18-1 (S)-N-(1-phenylpropyl)-3-bromo-2-phenylquinoline-4-carboxamide 
• 174636-20-5 2-phenyl-4-(carboxy-(S)-α-ethylbenzylamine)quinoline 
• 74-88-4 methyl iodide 
• 2941-20-0 1-phenylpropylamine 
• 2941-20-0 1-phenylpropylamine 

Relevant articles and documents

Functionalization through lithiation of (S)-N-(1-phenylpropyl)-2- phenylquinoline-4-carboxamide. Application to the labeling with carbon-11 of NK-3 receptor antagonist SB 222200

Lithiation of (S)-N-(1-phenylpropyl)-2-phenylquinoline-4-carboxamide with the complex n-BuLi/TMEDA (1/1 molar ratio) in THF at -60 °C for 5 h occurred selectively at the position 3 of the quinoline ring. This selectivity was shown by the absence of racemi

Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 2. Identification of (S)-N-(1-phenylpropyl)-3- hydroxy-2-phenylquinoline-4-carboxamide (SB 223412)

Optimization of the previously reported 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonist 14, with regard to potential metabolic instability of the ester moiety and affinity and selectivity for the human neurokinin-3 (hNK-3) receptor, is described. The ester functionality could be successfully replaced by the ketone (31) or by lower alkyl groups (Et, 21, or n-Pr, 24). Investigation of the substitution pattern of the quinoline ring resulted in the identification of position 3 as a key position to enhance hNK-3 binding affinity and selectivity for the hNK-3 versus the hNK-2 receptor. All of the chemical groups introduced at this position, with the exception of halogens, increased the hNK-3 binding affinity, and compounds 53 (3-OH, SB 223412, hNK- 3-CHO binding K(i) = 1.4 nM) and 55 (3-NH2, hNK-3-CHO binding K(i) = 1.2 nM) were the most potent compounds of this series. Selectivity studies versus the other neurokinin receptors (hNK-2-CHO and hNK-1-CHO) revealed that 53 is about 100-fold selective for the hNK-3 versus hNK-2 receptor, with no affinity for the hNK-1 at concentrations up to 100 μM. In vitro studies demonstrated that 53 is a potent functional antagonist of the hNK-3 receptor (reversal of senktide-induced contractions in rabbit isolated iris sphincter muscles and reversal of NKB-induced Ca2+ mobilization in CHO cells stably expressing the hNK-3 receptor), while in vive this compound showed oral and intravenous activity in NK-3 receptor-driven models (senktide-induced behavioral responses in mice and senktide-induced miosis in rabbits). Overall, the biological data indicate that (S)-N-(1-phenylpropyl)-3-hydroxy- 2-phenylquinoline-4-carboxamide (53, SB 223412) may serve as a pharmacological tool in animal models of disease to assess the functional and pathophysiological role of the NK-3 receptor and to establish therapeutic indications for non-peptide NK-3 receptor antagonists.