41058-67-7

Usage

Application

Spiro[cyclopentane-1,3'-indol]-2'(1'H)-one is a useful research chemical.

Upstream product

• 4669-18-5 spiro[cyclopentane-1,2'-indolin]-3'-one 
• 628-21-7 1,4-Diiodobutane 
• 59-48-3 2-oxoindole 
• 3400-45-1 cyclopentanecarboxylic acid 
• 613-94-5 benzoic acid hydrazide 
• 110-52-1 1,4-dibromo-butane 
• 50624-65-2 3-(1H-indol-3-yl)propyl bromide 
• 214610-10-3 N-boc-2-oxyindole 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 100-63-0 phenylhydrazine 
• 1422148-74-0 1-(2-bromophenyl)cyclopentanecarboxamide 
• 1422149-02-7 N-acetyl-1-(2-bromophenyl)cyclopentanecarboxamide 
• 143328-17-0 1-(2-bromophenyl)cyclopentanecarbonitrile 
• 19472-74-3 2-(2-bromophenyl)acetonitrile 

Downstream Products

• 304876-16-2 5-bromospiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one 
• 516517-55-8 C₁₈H₁₆ClNO 
• 304875-56-7 5'-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one 

Relevant academic research and scientific papers

ACTION OF tert-BUTYL AZIDOFORMATE ON THE CONJUGATE BASES OF 1,2,3,4-TETRAHYDRO-9H-CARBAZOLE AND OTHER INDOLE DERIVATIVES

tert-Butyl azidoformate (2) reacts with the conjugate bases of 3a, 7a, 9 (R1 = R2 = CH3), and 9 (R1 = CH3, R2 = H) to give products in addition to the expected N-(tert-butoxycarbinol)indole derivatives.

A Stereoselective Transformation of Pseudoindoxyls into Oxindoles in a Single Operation

The Aristotelia alkaloid (+)-aristotelone (1), a spiro-pseudoindoxyl derivative, is transformed in over 90 percent yield into the oxindole (+)-3-epitasmanine (3) upon treatment with hot BF3*Et2O in CH2Cl2.This intriguing transformation possibly proceeds through the intermediate 3-hydroxyindolenine derivative (-)-serratoline (2) which could be isolated when the reaction was run under milder conditions.This rearrangement, for which there is little precedent, is highly stereoselective in that the lactam carbonyl group ends up on the same face of the molecule as the C=O-unit of the starting pseudoindoxyl.That this outcome is due to a kinetic cont rol was demonstrated by showing that the epimeric starting material (-)-4 furnished exclusively the naturally occuring alkaloid (-)-tasmanine (5) under the same reaction conditions.

Discovery of Sisunatovir (RV521), an Inhibitor of Respiratory Syncytial Virus Fusion

RV521 is an orally bioavailable inhibitor of respiratory syncytial virus (RSV) fusion that was identified after a lead optimization process based upon hits that originated from a physical property directed hit profiling exercise at Reviral. This exercise encompassed collaborations with a number of contract organizations with collaborative medicinal chemistry and virology during the optimization phase in addition to those utilized as the compound proceeded through preclinical and clinical evaluation. RV521 exhibited a mean IC50 of 1.2 nM against a panel of RSV A and B laboratory strains and clinical isolates with antiviral efficacy in the Balb/C mouse model of RSV infection. Oral bioavailability in preclinical species ranged from 42 to >100% with evidence of highly efficient penetration into lung tissue. In healthy adult human volunteers experimentally infected with RSV, a potent antiviral effect was observed with a significant reduction in viral load and symptoms compared to placebo.

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

LACTAM COMPOUND AS FXR RECEPTOR AGONIST

Disclosed is a compound as shown in formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and the present invention relates to the use of same in the preparation of a drug for treating FXR-related diseases.

SPIRO[CYCLOPENTANE-1,3'-INDOLIN]-2'-ONE DERIVATIVES AS BROMODOMAIN INHIBITORS

The present invention provides spiro[cyclopentaneane-1,3'-indolin]-2'-one derivatives of formula (I), which are therapeutically useful, more particularly as bromodomain inhibitors. (I) wherein Cy, R1, R2, L and 'm' have the meaning given in the specification, and pharmaceutically acceptable salts or pharmaceutically acceptable stereoisomers thereof that are useful in the treatment and prevention of diseases or disorders, in particular their use as bromodomain inhibitors in the treatment and prevention of the associated diseases or disorders. The present invention also provides preparation of the compounds and pharmaceutical formulations comprising at least one of the spiro[cyclopentane-1,3'-indolin]-2'-one derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent or excipient therefore.

5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE

Provided are 5-HT2C receptor agonists. Also provided are methods for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea. Also provided are compositions comprising a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent, and methods for reducing the frequency of smoking tobacco in an individual attempting to reduce frequency of smoking tobacco; aiding in the cessation or lessening of use of a tobacco product in an individual attempting to cease or lessen use of a tobacco product; aiding in smoking cessation and preventing associated weight gain; controlling weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; reducing weight gain associated with smoking cessation by an individual attempting to cease smoking tobacco; treating nicotine dependency, addiction and/or withdrawal in an individual attempting to treat nicotine dependency, addiction and/or withdrawal; or reducing the likelihood of relapse use of nicotine by an individual attempting to cease nicotine use comprising administering a selective 5-HT2C receptor agonist, optionally in combination with a supplemental agent.

PHARMACEUTICAL COMPOUNDS

Benzimidazoles of formula (I): wherein: A is 5- to 12-membered aryl or 5- to 12-membered heteroaryl, each of which is unsubstituted or substituted; Y is a single bond, —(CH2)p—, —X—, —CH2—X—, or —X—CH2—; X is —O—, —S—, —N(R2)—, >C═O, >S(═O), >S(═O)2, —O—C(═O)—, —C(═O)—O—, N(R2)—C(═O)—, or —C(═O)—N(R2)—; each L is independently a single bond, C1-3alkylene, C2-3alkenylene or C2-3alkynylene; R1 is C1-6alkyl, C2-6alkenyl or C2-6alkynyl, each of which is unsubstituted or substituted; each Z is independently —N(R2)2, —OR2, —SR2, —S(═O)R2, —S(═O)2R2; each R2 is independently hydrogen, C1-6alkyl, C2-6alkenyl or C2-6 alkynyl, wherein said alkyl, alkenyl and alkynyl groups are unsubstituted or substituted; m is 0, 1, 2, or 3; n is 1, 2, or 3; and p is 1, 2, or 3; and the pharmaceutically acceptable salt thereof are inhibitors of RSV and can therefore be used to treat or prevent an RSV infection.

Efficient copper-catalyzed intramolecular N-arylation for the synthesis of oxindoles

An efficient copper-catalyzed intramolecular N-arylation was performed by using substituted 2-(2-bromoaryl)acetamide with a small amount of Cu 2O and benzene-1,2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields of oxindoles with tolerance of a wide variety of substrates.

PHARMACEUTICAL COMPOUNDS

Benzimidazoles of formula (I): wherein: A is 5-to 12-membered aryl or 5-to 12-membered heteroaryl, each of which is unsubstituted or substituted; Y is a single bond, -(CH2)p-, -X-, -CH2-X-, or -X-CH2-; X is -O-, -S-, -N(R2)-, >C=O, >S(=O), >S(=O)2, -O-C(=O)-, -C(=O)-O-, N(R2)-C(=O)-, or -C(=O)-N(R2)-; each L is independently a single bond, C1-3alkylene, C2-3alkenylene or C2-3alkynylene; R1is C1-6alkyl, C2-6alkenyl or C2-6alkynyl, each of which is unsubstituted or substituted; each Z is independently -N(R2)2, -OR2, -SR2, -S(=O)R2, -S(=O)2R2; each R2 is independently hydrogen, C1-6alkyl, C2-6alkenyl or C2-6 alkynyl, wherein said alkyl, alkenyl and alkynyl groups are unsubstituted or substituted; m is 0, 1, 2, or 3; n is 1, 2, or 3; and p is 1, 2, or 3; and the pharmaceutically acceptable salt thereof are inhibitors of RSV and can therefore be used to treat or prevent an RSV infection.