347-88-6

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 100-01-6 4-nitro-aniline 
• 366-63-2 4-fluoro-N-phenylbenzamide 
• 62-53-3 aniline 
• 456-22-4 4-Fluorobenzoic acid 
• 1590389-14-2 potassium trifluoro(4-fluorobenzoyl)borate 

Downstream Products

• 186544-90-1 N-(4-Amino-phenyl)-4-fluoro-benzamide 
• 1257095-97-8 C₂₆H₁₆F₂N₄O₄S₂ 
• 189806-34-6 N-[3-(2-dimethylaminoethyl)-2-methyl-1H-indol-5-yl]-4-fluorobenzamide 
• 186544-89-8 4-fluoro-N-(4-hydrazino-phenyl)-benzamide 

Relevant academic research and scientific papers

Discovery of novel VEGFR-2 inhibitors embedding 6,7-dimethoxyquinazoline and diarylamide fragments

VEGF/VEGFR-2 signaling plays a critical part in tumor angiogenesis. Inhibition of this pathway has been considered as a promising approach for cancer treatment. In this work, a series of 6,7-dimethoxy-4-anilinoquinazoline derivatives bearing diarylamide moiety were designed, synthesized and evaluated as potent inhibitors of VEGFR-2 kinase. Their in vitro antiproliferation activities against two human cancer cell lines Hep-G2 and MCF-7 have also been determined. Among them, compound 14b exhibited the most potent inhibitory activity against VEGFR-2 with IC50 value of 0.016 ± 0.002 μM and it showed the most potent antiproliferative effect against Hep-G2 and MCF-7 with IC50 values at low-micromolar range. Molecular docking studies revealed that these compounds represented by the most potent compound 14b could bind well to the ATP-binding site of VEGFR-2, which suggested that compound 14b could be a potential anticancer agent targeting VEGFR-2.

Synthesis of ring-opened derivatives of triazole-containing quinolinones and their antidepressant and anticonvulsant activities

Based on the potent antidepressant and anticonvulsant activities of the triazole-containing quinolinones reported in our previous work, a series of ring-opened derivatives of them were designed, synthesized in this work. Their antidepressant and anticonvulsant activities were screened using the forced swimming test (FST) and the maximal electroshock seizure test (MES), respectively. The results showed that compounds 4a, 5a, 6c-6e, 6g-6i, and 7 led to significant reductions in the accumulated immobility time in the FST at a dose of 50 mg/kg. Especially compound 7 exhibited higher levels of efficacy than the reference standard fluoxetine in the FST and the tail suspension test. The results of an open field test excluded the possibility of central nervous stimulation of 7, which further confirmed its antidepressant effect. Meanwhile, compounds 6a-6i and 7 showed different degrees of anticonvulsant activity in mice at the doses range from 300 to 30 mg/kg in the MES. Among them, compounds 6e and 7 displayed the ED50 of 38.5 and 32.7 mg/kg in the MES, and TD50 of 254.6 and 245.5 mg/kg, respectively. No one showed neurotoxicity at the dose of 100 mg/kg. The preliminary investigation forward to their mechanism indicated that regulation of GABAergic system might contribute to their anticonvulsive and anti-depressive action.

Chemoselective acylation of primary amines and amides with potassium acyltrifluoroborates under acidic conditions

Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.

Effective nitration of anilides and acrylamides by tert-butyl nitrite

Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.

N-[3-(2-dimethylaminoethyl).2-methyl-1H-indol-5-yl]-4-fluorobenzamide: A potent, selective, and orally active 5-HT1F receptor agonist potentially useful for migraine therapy

Recent studies have demonstrated that selective 5-HT1F receptor agonists inhibit neurogenic dural inflammation, a model of migraine headache, indicating that these compounds may be effective therapies for the treatment of migraine pain. This communication describes the synthesis and discovery of a novel compound, N-[3-(2-(dimethylamino)-ethyl)-2-methyl-1H-indol-5-yl]-4-fluorobenzamide (4), which possesses high binding affinity and selectivity at the 5-HT1F receptor relative to more than 40 other serotonergic and nonserotonergic receptors examined.

METHODS OF TREATING OR AMELIORATING THE SYMPTOMS OF COMMON COLD OR ALLERGIC RHINITIS WITH SEROTONIN 5-HT1F

This invention provides methods for the treatment or amelioration of the symptoms of the common cold or allergic rhinitis which comprises administering to a mammal in need thereof a serotonin 5-HT 1F agonist.

Use of a serotonin 5-HTlf agonist in the manufacture of a medicament for treating or ameliorating the symptoms of common cold or allergic rhinitis

This invention provides methods for the treatment or amelioration of the symptoms of the common cold or allergic rhinitis which comprises administering to a mammal in need thereof a serotonin 5-HT1F agonist.

Use of serotonin 5-HT1F agonists for the prevention of migraine

This invention provides methods for the prevention of migraine which comprises administering to a mammal in need thereof a serotonin 5-HT1F agonist.

6-SUBSTITUTED-1,2,3,4-TETRAHYDRO-9H-CARBAZOLES AND 7-SUBSTITUTED-10H-CYCLOHEPTA [7,6-B]INDOLES: NEW 5-HT1F AGONISTS

This invention provides novel 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta[7,6-b]indoles. These compounds are 5-HT 1F agonists which are useful for the treatment of migraine and associated disorders.