53429-14-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(5-Phenylpentyl)-1H-isoindole-1,3(2H)-dione is used as an antipsychotic medication for the treatment of various mental disorders, including schizophrenia, bipolar disorder, and major depressive disorder. Its unique mechanism of action, which involves modulating the activity of dopamine and serotonin receptors, makes it an effective treatment option for these conditions.
Used in Schizophrenia Treatment:
Aripiprazole is used as a therapeutic agent for schizophrenia, a chronic mental disorder characterized by delusions, hallucinations, and disorganized thinking. By acting as a partial agonist at dopamine D2 receptors, it helps alleviate the positive symptoms of schizophrenia, such as hallucinations and delusions.
Used in Bipolar Disorder Management:
In the case of bipolar disorder, a condition marked by extreme mood swings, aripiprazole is used as a mood stabilizer. Its action as a partial agonist at dopamine D2 and serotonin 5-HT1A receptors, along with its antagonist activity at serotonin 5-HT2A receptors, helps in managing both manic and depressive episodes.
Used in Major Depressive Disorder Treatment:
Aripiprazole is also used as an adjunctive treatment for major depressive disorder, where it is combined with antidepressant medications to enhance their therapeutic effects. Its unique mechanism of action helps improve the symptoms of depression by modulating the levels of dopamine and serotonin in the brain.
Aripiprazole is available in various forms, such as tablets, orally disintegrating tablets, and liquid, allowing for flexible administration options. It is typically taken once daily, and it is crucial to follow the dosage instructions provided by a healthcare professional. Potential side effects, such as drowsiness, headache, and weight gain, should also be considered when using this medication.

Upstream product

• 136918-14-4 phthalimide 
• 14469-83-1 (5-bromopentyl)benzene 
• 10521-91-2 5-phenylpentan-1-ol 
• 98-80-6 phenylboronic acid 
• 954-81-4 N-(5-bromopentyl)phthalimide 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 53429-15-5 5-phenyl-1-pentylamine hydrochloride 
• 144477-84-9 N-[3-(1H-Imidazol-4-yl)-propyl]-N'-(5-phenyl-pentyl)-guanidine; hydrochloride 
• 144290-37-9 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-(5-phenyl-pentyl)-guanidine 
• 899443-21-1 5-isocyanatopentylbenzene 
• 17734-21-3 5-phenylpentylamine 

Relevant academic research and scientific papers

Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization

The installation of trifluoromethyl groups has become an essential step across a number of industries such as agrochemicals, drug discovery, and materials. Consequently, the rapid introduction of this critical functional group in a predictable fashion would benefit current practitioners in those fields. This communication describes a mild trifluoromethylation of benzylic C-H bonds with high selectivity for the least hindered hydrogen atom. The reaction provides monotrifluoromethylation and proceeds in an environmentally friendly acetone/water solvent system. The method can be used to install benzylic trifluoromethyl groups on highly functionalized drug molecules.

SUBSTITUTED BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to substituted benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides substituted benzoxazolone derivatives for use in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies

Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

ACID CERAMIDASE INHIBITORS AND THEIR USE AS MEDICAMENTS

The present invention concerns, in a first aspect, compounds of Formula I as defined herein, pharmaceutically acceptable salts thereof and pharmaceutical compositions containing such compounds. The present invention also relates to compounds of Formula I

ACID CERAMIDASE INHIBITORS AND THEIR USE AS MEDICAMENTS

The present invention concerns, in a first aspect, compounds of Formula I as defined herein, pharmaceutically acceptable salts thereof and pharmaceutical compositions containing such compounds. The present invention also relates to compounds of Formula I

Discovery of potent inhibitors of human and mouse fatty acid amide hydrolases

Fatty acid amide hydrolase (FAAH, EC 3.5.1.99) is the main enzyme catabolizing endocannabinoid fatty acid amides. FAAH inactivation promotes beneficial effects upon pain and anxiety without the side effects accompanying agonists of type-1 cannabinoid receptors. Aiming at discovering new selective FAAH inhibitors, we developed a series of compounds (5a-u) characterized by a functionalized heteroaromatic scaffold. Particularly, 5c and 5d were identified as extremely potent, noncompetitive, and reversible FAAH inhibitors endowed with a remarkable selectivity profile and lacking interaction with the hERG channels. In vivo antinociceptive activity was demonstrated for 5c, 5d, and 5n at a dose much lower than that able to induce either striatal and limbic stereotypies or anxiolytic activity, thus outlining their potential to turn into optimum preclinical candidates. Aiming at improving pharmacokinetic properties and metabolic stability of 5d, we developed a subset of nanomolar dialyzable FAAH inhibitors (5v-z), functionalized by specific polyethereal lateral chains and fluorinated aromatic rings.

Copper-catalyzed cross-coupling reaction of organoboron compounds with primary alkyl halides and pseudohalides

Non-activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper-catalyzed cross-coupling with aryl boron compounds and alkyl 9-BBN reagents (see scheme; 9-BBN=9-borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium- and nickel-catalyzed Suzuki-Miyaura coupling reactions of alkyl halides.

Unusually Long Lifetimes of the Singlet Derived from 4-Azido-2,3,5,6-tetrafluorobenzamides

Laser flash photolysis (308 nm, 20 ns, 150 mJ) of 4-azido-2,3,5,6-tetrafluorobenzamides, esters, and thioesters generate singlet nitrenes which can be intercepted with pyridine to produce strongly absorbing ylides.It was possible to resolve the rate of formation of the ylides as a function of pyridine concentration.This has lad to direct measurements of the absolute rate constants of (a) the reaction of the nitrene with pyridine, (b) ring expansion of the nitrene to a ketenimine, and (c) singlet to triplet nitrene intersystem crossing.

Monocyclic Pteridine Analogues. Inhibition of Escherichia coli Dihydropteroate Synthase by 6-Amino-5-nitrosoisocytosines

A variety of 5,6-disubstituted isocytosine derivatives were evaluated in vitro as inhibitors of dihydropteroate synthase from Escherichia coli.A number of 6-(alkylamino)-5-nitrosoisocytosines have in vitro potency equivalent with or superior to that of therapeutically effective sulfonamide inhibitors of the synthase.The sulfonamide drugs are known to complete for the p-aminobenzoic acid binding site of the synthase, and kinetic analysis of inhibition of the synthase by 6-(methylamino)-5-nitrosoisocytosine (16; I50 = 1.6 μM) and by the 6-(3-phenoxypropyl)amino analogue (33; I50 = 3.7 μM) indicated that the nitrosoisocytosine inhibitors compete with the pteridine substrate for the enzyme.Structure-activity studies demonstrated that the enzyme surface has a low tolerance for steric bulk in the region surrounding the isocytosine 6-amino function.However, this steric intolerance may be counterbalanced to a significant degree by positive allosteric interactions achieved by certain analogues that have a 6-(ω-phenylalkyl)amino substituent.For example, 6--5-nitrosoisocytosine (28) is as effective an inhibitor (I50 = 1.4 μM) as the 6-methylamino compound 16.Although several members of the 5-nitroso series were potent synthase inhibitors, none of the nitrosoisocytosines exhibited significant antibacterial activity.This observation may reflect poor transport of these compounds through the bacterial cell wall or, alternatively, may result from a rapid metabolic inactivation process.