99686-98-3

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 91-56-5 indole-2,3-dione 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 

Downstream Products

• 30081-49-3 methyl 2,3-diphenylquinoline-4-carboxylate 
• 1298069-39-2 C₂₈H₂₀N₂O 
• 1298069-40-5 C₂₃H₁₈N₂O 
• 30081-50-6 2,3-diphenylquinoline-4-carboxamide 
• 30081-52-8 2,3-diphenyl-quinoline-4-carbonyl chloride 
• 30081-53-9 6-phenyl-indeno[1,2-c]quinolin-11-one 

Relevant academic research and scientific papers

Synthesis of some 2-aryl- and 2,3-diaryl-quinolin-4-carboxylic acid derivatives

Eighteen 2-aryl- and 2,3-diaryl-quinolin-4-carboxlic acid derivatives were synthesized. Basically, the synthetic design of these compounds arose from the appropriate disconnections of the target compounds, which revealed pyruvic acid, aromatic amine, and benzaldehyde or phenyl pyruvic acid, aromatic amine, and benzaldehyde as possible logical precursors for 2-aryl- and 2,3-aryl-quinolin-4- carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques (ultraviolet, infrared, mass, 1H NMR, and 13C NMR). The prepared derivatives were screened for their antibacterial activity against the standard bacterial organisms B. subtilis, S. aureus, E. coli, and P. vulgaris. 2,3-Diphenyl-6-sulfanilamido-quinolin-4-carboxylic acid showed the highest activity against the four tested organisms.

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.