50424-96-9

Upstream product

• 33844-21-2 2-nitro-4-methoxybenzoic acid 

Downstream Products

• 855939-06-9 2-diazo-1-(4-methoxy-2-nitro-phenyl)-ethanone 
• 67323-06-2 1-(4-methoxy-2-nitrophenyl)ethanone 
• 27037-34-9 7-methoxyquinoline-2,4-diol 
• 1026319-38-9 4-Methoxy-2-nitro-benzoyl azide 
• 131632-14-9 1-[1-(2-Amino-4-methoxy-benzoyl)-piperidin-4-yl]-3,4-dihydro-1H-quinolin-2-one 
• 131632-12-7 1-[1-(4-Methoxy-2-benzyloxycarbonylaminobenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril 
• 176547-25-4 {5-Methoxy-2-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)-piperidine-1-carbonyl]-phenyl}-methyl-carbamic acid benzyl ester 
• 131631-96-4 Ethyl-{5-methoxy-2-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)-piperidine-1-carbonyl]-phenyl}-carbamic acid benzyl ester 
• 131632-83-2 {5-Methoxy-2-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)-piperidine-1-carbonyl]-phenyl}-propyl-carbamic acid benzyl ester 
• 131631-99-7 (Benzyloxycarbonyl-{5-methoxy-2-[4-(2-oxo-3,4-dihydro-2H-quinolin-1-yl)-piperidine-1-carbonyl]-phenyl}-amino)-acetic acid ethyl ester 
• 213118-56-0 (2-amino-4-methoxyphenyl)carbamate tert-butyl ester 
• 185428-90-4 (4-methoxy-2-nitro-phenyl)-carbamic acid tert-butyl ester 
• 942220-44-2 1-Benzyl-6-methoxy-1,3-dihydro-benzoimidazol-2-one 
• 1026308-74-6 1-Benzyl-2-chloro-6-methoxy-1H-benzoimidazole 

Relevant academic research and scientific papers

Anthranilic acid derivatives as nuclear receptor modulators - Development of novel PPAR selective and dual PPAR/FXR ligands

Nuclear receptors, especially the peroxisome proliferator activated receptors (PPARs) and the farnesoid X receptor (FXR) fulfill crucial roles in metabolic balance. Their activation offers valuable therapeutic potential which has high clinical relevance w

Extending the structure-activity relationship of anthranilic acid derivatives as farnesoid x receptor modulators: Development of a highly potent partial farnesoid x receptor agonist

The ligand activated transcription factor nuclear farnesoid X receptor (FXR) is involved as a regulator in many metabolic pathways including bile acid and glucose homeostasis. Therefore, pharmacological activation of FXR seems a valuable therapeutic approach for several conditions including metabolic diseases linked to insulin resistance, liver disorders such as primary biliary cirrhosis or nonalcoholic steatohepatitis, and certain forms of cancer. The available FXR agonists, however, activate the receptor to the full extent which might be disadvantageous over a longer time period. Hence, partial FXR activators are required for long-term treatment of metabolic disorders. We here report the SAR of anthranilic acid derivatives as FXR modulators and development, synthesis, and characterization of compound 51, which is a highly potent partial FXR agonist in a reporter gene assay with an EC50 value of 8 ± 3 nM and on mRNA level in liver cells.

Synthesis and Quantitative Structure-Activity Relationships of Selective BCRP Inhibitors

The breast cancer resistance protein (BCRP/ABCG2) is a member of the ABC transporter superfamily. This protein has a number of physiological functions, including protection of the human body from xenobiotics. The overexpression of BCRP in certain tumor cell lines causes cross-resistance against various drugs used in chemotherapeutic treatment. In a previous work we showed that a new class of compounds derived from XR9576 (tariquidar) selectively inhibits BCRP. In this work we synthesized more members of this class, with modification on the second and third aromatic rings. The inhibitory activities against BCRP and P-gp were assayed using a Hoechst 33342 assay for BCRP and a calcein AM assay for P-gp. Finally, quantitative structure-activity relationships for both aromatic rings were established. The results obtained show the importance of the electron density on the third aromatic ring, influenced by substituents, pointing to interactions with aromatic residues of the protein binding site. In the second aromatic ring the activity of compounds is influenced by the steric volume of the substituents.

Synthesis, biological evaluation, and structure-activity relationships of 2-[2-(benzoylamino)benzoylamino]benzoic acid analogues as inhibitors of adenovirus replication

2-[2-Benzoylamino)benzoylamino]benzoic acid (1) was previously identified as a potent and nontoxic antiadenoviral compound (Antimicrob. Agents Chemother. 2010, 54, 3871). Here, the potency of 1 was improved over three generations of compounds. We found that the ortho, ortho substituent pattern and the presence of the carboxylic acid of 1 are favorable for this class of compounds and that the direction of the amide bonds (as in 1) is obligatory. Some variability in the N-terminal moiety was tolerated, but benzamides appear to be preferred. The substituents on the middle and C-terminal rings were varied, resulting in two potent inhibitors, 35g and 35j, with EC50 = 0.6 μM and low cell toxicity.

Synthesis and SAR of potent inhibitors of the Hepatitis C virus NS3/4A protease: Exploration of P2 quinazoline substituents

Novel NS3/4A protease inhibitors comprising quinazoline derivatives as P2 substituent were synthesized. High potency inhibitors displaying advantageous PK properties have been obtained through the optimization of quinazoline P2 substituents in three series exhibiting macrocyclic P2 cyclopentane dicarboxylic acid and P2 proline urea motifs. For the quinazoline moiety it was found that 8-methyl substitution in the P2 cyclopentane dicarboxylic acid series improved on the metabolic stability in human liver microsomes. By comparison, the proline urea series displayed advantageous Caco-2 permeability over the cyclopentane series. Pharmacokinetic properties in vivo were assessed in rat on selected compounds, where excellent exposure and liver-to-plasma ratios were demonstrated for a member of the 14-membered quinazoline substituted P2 proline urea series.

3,4-DIHYDRO-2 (1H) - QUINOLINONE AND 2 (1H)-QUINOLINONE DERIVATIVES

The present invention relates to novel 3,4-dihydro-2(lH)-quinolinone and 2(lH)-quinolinone derivatives, their acceptable acid addition salts, solvates, hydrates and polymorphs thereof. The invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by atypical antipsychotic agents. The invention further provides methods for using a compound of this invention to determine concentrations of a corresponding 3,4-dihydro-2(lH)- quinolinone or 2(lH)-quinolinone compound, particularly in biological fluids, and to determine metabolism patterns of that 3,4-dihydro-2(lH)-quinolinone or 2(1H)-quinolinone compound.

A short synthesis of koniamborine, a naturally occurring pyrano[3,2-b]indole

An expedient synthesis of the alkaloid koniamborine, the only to date isolated naturally occurring pyrano[3,2-b]indole is presented. The key pyrano[3,2-b]indole forming step is a palladium-catalyzed reductive N-heteroannulation of 2-(4-methoxy-2-nitrophen

ORGANIC COMPOUNDS

The present invention relates to quinazolinone compounds of the formula wherein R2, R3, R5, R6 R7 and R8 are as defined in the specification and in the claims, in free form or in salt form , processes for their preparation and their use as pharmaceuticals, particularly in the treatment of disorders ameliorated by administration of TRPV1 antagonists.

Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines

Palladium-catalyzed cross-couplings represent a powerful method for the formation of new bonds. A catalytic, enantioselective P-C bond-forming reaction proceeding via a Pd-mediated arylation of silylphosphines was developed for the synthesis of P-stereoge

New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation

A series of 2-piperazinylbenzimidazole derivatives were prepared and evaluated as 5-HT3 receptor antagonists. Their 5-HT3 receptor affinities were evaluated by radioligand binding assays, and their abilities to inhibit the 5-HT-induced Bezold-Jarisch reflex in anesthetized rats were determined. Compound 7e (lerisetron, pK(i) = 9.2) exhibited higher affinity for the 5- HT3 receptor than did tropisetron and granisetron, while compound 7q (pK(i) = 7.5) had very low affinity for this receptor, showing that substitution on the N1 atom of the benzimidazole ring is essential for affinity and activity. The effect of substitution on the aromatic ring of benzimidazole by several substituents in different positions is also discussed. A strong correlation between the 5-HT3 antagonistic activity of the studied compounds and the position of substitution on the aromatic ring was established. Thus, while the 4-methoxy derivative 7m showed weak affinity for the 5-HT3 receptor (pK(i) = 6.7), the 7-methoxy derivative 7n exhibited the highest affinity (pK(i) = 9.4). Compounds 7e and 7n are now under further investigation as drugs for the treatment of nausea and emesis evoked by cancer chemotherapy and radiation.