19155-24-9

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dihydro-3,3-dimethyl-2H-indol-2-one is used as an isoquinolin-1-amine based ROCK-I inhibitor for its ability to modulate specific cellular signaling pathways. This makes it a promising candidate for the development of novel therapeutics targeting various diseases and conditions.
Additionally, it is used in the preparation of P2Y1 antagonists, which are effacacious antiplatelet agents. These agents have potential applications in the treatment and prevention of thrombotic disorders, where they can help reduce the risk of blood clot formation and related complications.

Synthesis Reference(s)

Tetrahedron, 48, p. 7297, 1992 DOI: 10.1016/S0040-4020(01)88268-5

InChI:InChI=1/C10H11NO/c1-10(2)7-5-3-4-6-8(7)11-9(10)12/h3-6H,1-2H3,(H,11,12)

Upstream product

• 67-56-1 methanol 
• 1504-06-9 3-methylindolin-2-one 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 99984-56-2 3,3-dimethyl-3H-indole-2-carbonitrile 
• 5461-50-7 isobutyric acid-(N'-phenyl-hydrazide) 
• 27333-47-7 1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b](1,4)-oxazine] 
• 112169-80-9 1-phenylcarbamoyl-3,3-dimethyloxindole 
• 72934-84-0 1-acetyl-3,3-dimethylindolin-2-one 
• 1592-43-4 1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran] 
• 75997-02-3 1-(methoxydiphenylmethyl)-3,3-dimethyloxindole 
• 154078-57-6 2-(2-Amino-phenyl)-N-phenyl-isobutyramide 
• 154078-55-4 2-(2-Amino-phenyl)-N-(4-methoxy-phenyl)-isobutyramide 
• 154078-59-8 N-(4-Acetyl-phenyl)-2-(2-amino-phenyl)-isobutyramide 

Downstream Products

• 1914-02-9 3,3-dimethylindoline 
• 872271-71-1 5,7-dibromo-3,3-dimethyl-indolin-2-one 
• 122281-20-3 5-<(2-bromo-1-oxo)propyl>-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 
• 122281-03-2 5-<(2-chloro-1-oxo)propyl>-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 
• 185199-35-3 (S)-(+)-5-(2-chloro-1-oxo)propyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 
• 100511-00-0 1,3-Dihydro-3,3-dimethyl-5-nitro-2H-indol-2-one 
• 120902-45-6 5-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one 
• 910562-95-7 benzyl [[(3,3-dimethyl-2-oxo-1-indolinyl)carbonyl]-methyl]carbamate 
• 910562-97-9 benzyl 2,3,9,9a-tetrahydro-9,9-dimethyl-3-oxo-1H-imidazo[1,2-a]indole-3-carboxylate 
• 910562-96-8 benzyl [[(2-hydroxy-3,3-dimethyl-1-indolinyl)carbonyl]-methyl]carbamate 
• 304874-59-7 5-(3-methoxyphenyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one 
• 304874-60-0 5-(3-chlorophenyl)-3,3-dimethyl-1,3-dihydro-2H-indole-2-one 
• 100643-96-7 indolidan 
• 118825-14-2 2-Benzylthio-3,3-dimethyl-3H-indole 

Relevant academic research and scientific papers

Dirhodium(ii) tetraacetate catalysed reactions of diazo thioamides: Isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomuenchnones), an approach to analogues of dehydrogliotoxin

Dirhodium(II) tetraacetate catalysed reaction of the indoline diazo thioamide 8 gives the thioisomuenchnone 9, a stable characterisable solid. This masked thiocarbonyl ylide undergoes 1, 3-dipolar cycloaddition with N-methylmaleimide and maleic anhydride to give the exo-cycloadducts 10 and 11, characterised by X-ray crystallography. The thioisomuenchnone 18, derived from diazo thioamide 17, is an extremely stable crystalline mesoionic system which can be characterised by X-ray crystallography but fails to undergo intramolecular cycloaddition. The related thioisomnchnone 19 can be generated by reaction of indoline-2-thione 7 with bromoacetyl chloride in the presence of triethylamine, and undergoes cycloaddition, to give adducts 20 and 21.

Study of the Fatigue Process and the Yellowing of Polymeric Films Containing Spirooxazine Photochromic Compounds

Photochromic polyurethane films containing 5-substituted 1,3-dihydro-3,3-dimethyl-1-alkylspiropyridobenzoxazine> and 1,3-dihydro-1,3,3-trimethylspironaphthoxazine> were degraded under xenon light exposure.The loss of the photochromic response was monitored by spectrophotometry as a function of the irradiation time; meanwhile, the photoproduct formation and the amount of photochromic material still available were analyzed by chromatography after liquid-solid extraction.At the same time, the fade rateswere monitored after flash-excitation photolysis or after the photostationary state during degradation.It was clearly demonstrated that the loss of photochromism was due exclusively to a photooxidation process of the initial dye, and not to an acceleration of the bleaching or a potential screen effect caused by the photoproducts.

Preparation of Complexes Bearing N-Alkylated, Anionic or Protic CAACs Through Oxidative Addition of 2-Halogenoindole Derivatives

CAAC precursors 2-chloro-3,3-dimethylindole 1 and 2-chloro-1-ethyl-3,3-dimethylindolium tetrafluoroborate 2BF4 have been prepared and oxidatively added to [M(PPh3)4] (M=Pd, Pt). Salt 2BF4 reacts with [Pd(PPh3)4] in toluene at 25 °C over 4 days to yield complex cis-[3]BF4 featuring an N-ethyl substituted CAAC, two cis-arranged phosphines and a chloro ligand. Compound trans-[3]BF4 was obtained from the same reaction at 80 °C over 1 day. Salt 2BF4 reacts with [Pt(PPh3)4] to give cis-[4]BF4. The neutral indole derivative 1 adds oxidatively to [Pt(PPh3)4] to give trans-[5] featuring a CAAC ligand with an unsubstituted ring-nitrogen atom. This nitrogen atom has been protonated with py?HBF4 to give trans-[6]BF4 bearing a protic CAAC ligand. The PdII complex trans-[7]BF4 bearing a protic CAAC ligand was obtained in a one-pot reaction from 1 and [Pd(PPh3)4] in the presence of py?HBF4.

Influenza virus replication inhibitors and uses thereof

The invention belongs to the field of medicines, and particularly relates to novel compounds serving as an influenza virus replication inhibitor, a preparation method thereof, a pharmaceutical composition containing the compounds and application of the compounds and the pharmaceutical composition in treatment of influenza. The compounds are compounds as shown in a formula (I) or a stereoisomer, a tautomer, a nitrogen oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or prodrugs of the stereoisomer, the tautomer, the nitrogen oxide, the solvate, the metabolite and the pharmaceutically acceptable salt of the compound as shown in the formula (I). The compounds not only can well inhibit influenza viruses, but also have lower cytotoxicity, excellent in-vivo pharmacokinetic property and the in-vivo pharmacodynamic property and good liver microsome stability.

NOVEL COMPOUNDS USEFUL AS POLY(ADP-RIBOSE) POLYMERASE (PARP) INHIBITORS

The present invention provides novel poly(ADP-ribose) polymerase (PARP) inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods for the treatment, prevention and/or amelioration of PARP mediated diseases or disorders using them. In particular, the compounds described herein are useful for the treatment of carcinoma of the breast, ovarian cancer, carcinoma of the liver, carcinoma of the lung, small cell lung cancer, esophageal cancer, gall bladder cancer, pancreatic cancer and stomach cancer.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).

Kinase inhibitors (by machine translation)

The present invention relates to certain 4 - (substituted anilino) -2 - (substituted piperi -1 -yl) pyrimidine -5 - carboxamide compounds useful for the treatment or prevention of diseases or medical conditions mediated by signal transduction of CaMMK1 isotype. For example, such compounds and salts thereof may be used to treat or prevent a variety of different cancers. Diseases (including 2 diabetes) and/or immune-mediated diseases. (by machine translation)

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.

Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure

Herein we report our efforts of developing reversible selective hMAO-B inhibitors based on isatin, a fragment in an X-ray crystal structure. Five different scaffolds were designed and many compounds were synthesized. Among them, compound A3 demonstrated very high potency and isoform selectivity against hMAO-B, 11 and 13 times more potent (IC50 = 3 nM) and 23.64 and 6.8 times more selective than the marked drugs, selegiline and safinamide. However, the endeavors to modify the polar 3-one group of isatin, that is in a hydrophobic environment in the binding site of hMAO-B, to small nonpolar hydrophobic groups did not bring about improved hMAO-B inhibitors, which may challenge our understanding of molecular interactions and molecular recognition in biological systems.