366452-97-3

Basic information

• Product Name: 4-nitroisoindolin-1-one
• Synonyms: 4-nitroisoindolin-1-one;4-Nitro-2,3-dihydro-1H-isoindol-1-one;4-Nitro-2,3-dihydro-1H-isoindolin-1-one;4-Nitro-2,3-dihydro-isoindol-1-one;1H-Isoindol-1-one, 2,3-dihydro-4-nitro-
• CAS NO: 366452-97-3
• Molecular Formula: C8H6N2O3
• Molecular Weight: 178.14484
• Mol File: 366452-97-3.mol

Chemical Properties

• Boiling Point: 488.773 °C at 760 mmHg
• Flash Point: 249.401 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-nitroisoindolin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitroisoindolin-1-one(366452-97-3)
• EPA Substance Registry System: 4-nitroisoindolin-1-one(366452-97-3)

Safety Data

• Hazardous Substances Data: 366452-97-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitroisoindolin-1-one is used as a reactant for the synthesis of 4-(N-acyl)-2,3-dihydro-1H-isoindol-1-ones, which are potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). These inhibitors play a crucial role in the development of novel therapeutic strategies for the treatment of various diseases, particularly cancer.
In the synthesis process, 4-Nitroisoindolin-1-one serves as a key building block, providing a structural framework that can be further modified to create more complex and biologically active molecules. The resulting PARP-1 inhibitors have shown promise in targeting cancer cells by exploiting their increased reliance on PARP-1 for DNA repair, thereby enhancing the effectiveness of chemotherapy and radiation therapy.
Additionally, 4-Nitroisoindolin-1-one may also be utilized in other applications within the pharmaceutical industry, such as the development of new drugs targeting different enzymes or receptors, depending on the specific modifications and substitutions made to its core structure.

InChI:InChI=1/C8H6N2O3/c11-8-5-2-1-3-7(10(12)13)6(5)4-9-8/h1-3H,4H2,(H,9,11)

Upstream product

• 603-62-3 4-nitro-1H-isoindole-1,3(2H)-dione 
• 39830-63-2 3-hydroxy-4-nitroisoindolin-1-one 
• 59382-59-1 2-methyl-3-nitro-benzoic acid methyl ester 
• 98475-07-1 2-bromomethyl-3-nitro-benzoic acid methyl ester 

Downstream Products

• 295357-72-1 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid 
• 366454-36-6 EB-47 
• 366452-98-4 4-amino-2,3-dihydro-1H-isoindol-1-one 

Relevant articles and documents

HPK1 ANTAGONISTS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.

One-pot method to construct isoindolinones and its application to the synthesis of DWP205109 and intermediate of Lenalidomide

Herein a practical and efficient system for concise synthesis of isoindolinones is described by using substituted methyl 2-(halomethyl)benzoates and substituted amines. Structurally various methyl 2-(halomethyl)benzoates and amines were transformed into isoindolinones 80–99% yield and purity in catalyst-free and solvent-free conditions. The method has a wide substrate scope. The synthetic utility of the one-pot reaction was demonstrated by the concise syntheses of Lenalidomide intermediate and DWP205190.

Compound with dual inhibitory activity TDO, IDOO1 and application of compound for treating neurodegenerative disease (by machine translation)

The present invention provides a compound of formula I, or a pharmaceutically acceptable salt thereof, or a solvate thereof, which can selectively inhibit TDO, IDOO1, which has a significant inhibitory effect on TDO and/or IDOO1. In addition, the prepared compound has a remarkable anti-tumor effect, has a certain treatment effect on's disease and's disease, and has a good application prospect in the field of medicine preparation. (by machine translation)

Synthetic method of isoindolinone compound

The invention belongs to the field of chemical synthesis, and particularly relates to a synthesis method of an isoindolinone compound. The isoindolinone compound is represented by formula (I), in which R, R1 and R2 are used for representing any substituent groups. According to the synthetic method of the isoindolinone compound, a new process for solvent-free synthesis of the isoindolinone compoundis developed; no solvent is used, so that the separation and purification process of the product is easier to carry out, the green production of fine chemicals is effectively realized, the operationis simple, the reaction time is obviously shortened, the production efficiency of the product is increased, the quality and yield are improved, the yield can reach 81%-99%, and the purity can reach 96%-99%.

Small Molecule Microarray Based Discovery of PARP14 Inhibitors

Poly(ADP-ribose) polymerases (PARPs) are key enzymes in a variety of cellular processes. Most small-molecule PARP inhibitors developed to date have been against PARP1, and suffer from poor selectivity. PARP14 has recently emerged as a potential therapeutic target, but its inhibitor development has trailed behind. Herein, we describe a small molecule microarray-based strategy for high-throughput synthesis, screening of >1000 potential bidentate inhibitors of PARPs, and the successful discovery of a potent PARP14 inhibitor H10 with >20-fold selectivity over PARP1. Co-crystallization of the PARP14/H10 complex indicated H10 bound to both the nicotinamide and the adenine subsites. Further structure–activity relationship studies identified important binding elements in the adenine subsite. In tumor cells, H10 was able to chemically knockdown endogenous PARP14 activities.

Design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates

We report herein the design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates based on the structure of SB-222734. The antibacterial activities of these newly synthesized compounds were also evaluated and compared with linezolid and retapamulin. Results showed that most of the target compounds exhibit good potency in inhibiting the growth of Gram-positive bacteria including Methicillin- susceptible Staphylococcus aureus MSSA (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. aureus MRSA (MIC: 0.0625-2 μg/mL), Methicillin-susceptible Staphylococcus epidermidis MSSE (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. epidermidis MRSE (MIC: 0.0625-2 μg/mL), and Streptococcus pneumonia (MIC: 0.0625-4 μg/mL). In particular, three remarkable compounds of this series (12l, 12m, and 21l) exhibited comparable in vitro antibacterial profiles to that of retapamulin.

METHODS FOR SYNTHESIZING 3-(SUBSTITUTED DIHYDROISOINDOLINONE-2-YL)-2,6-DIOXOPIPERIDINE, AND INTERMEDIATES THEREOF

The present invention discloses methods for synthesizing 3-(substituted dihydroisoindolinone-2-yl)-2,6-dioxopiperidine and intermediates thereof, namely, the synthesis of compounds of the Formula (I), with each substitutional group defined in the patent specification. Owing to the advantages of high productivity, little influence to the environment and material accessibility, the methods of the present invention is suitable for industrial production.

SUBSTITUTED ARYL-AMINE DERIVATIVES AND METHODS OF USE

The present invention provides classes of compounds, including-their pharmaceutically acceptable derivatives, useful for treating angiogenesis and related diseases such as cancer. Formula I and II wherein R is a 9- or 10-membered heterocyclyl ring selected from 7-isoquinolinyl,..2-methyl-3-oxo-2,3-dihydroindazol-6-yl, [1,6]-naphthydrin-3-yl, [1,7]-naphthydrin-2-yl, 1-oxo-2,3-dihydrobenzofuran-4-yl, 3-oxo-2,3-dihydrobenzofuran-5-yl, dihydro-benzodioxinyl, 6-quinazolinyl, 2-amino-6-quinazolinyl, 4-methylamino-6-quinazolinyl, 2,4-diamino-6 quinazolinyl, 3-oxo-3,4-dihydro-1,4-benzoxazin-6-yl, 2,2-difluoro-l;3-benzodioxol-5-yl and 2,2,3,3 tetrafluoro-2,3-dihydro-l,4-benzodioxin-6-yl, each of which is optionally substituted with one or more substituents selected from halo, haloakyl, C1-6 alkyl, C2-8 alkenyl, C2-8 alkynyl, N-dimethylamino-C1-6-alkyl, N-dimethylamino-C1-6-alkoxy, amino, alkyl-carbonylamino, morpholino-sulfonyl, amino-sulfonyl, oxazolyl, pyrrolyl,4 morpholinyl, carboxyl, cyano, and acetyl; wherein R1 in formula I is selected from unsubstituted or substituted phenyl, 5-6 membered heteroaryl, 9-10 membered bicyclic heterocyclyl and 11-14 membered tricyclic heterocyclyl, and R1 in formula II is selected from specific bicyclic heterocycles.

The discovery and synthesis of novel adenosine substituted 2,3-dihydro-1H-isoindol-1-ones: Potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1)

A series of novel 4-(N-acyl)-2,3-dihydro-1H-isoindol-1-ones have been prepared from methyl-3-nitro-2-methylbenzoate and linked through various spacers to the adenosine derivatives 11 and 12. We found that potent inhibition of poly(ADP-ribose)polymerase-1 (PARP-1) was achieved when isoindolinone was linked to adenosine by a spacer group of a specific length. Introduction of piperazine and succinyl linkers between the isoindolinone and adenosine core structures resulted in highly potent compounds 8a and 10b, which showed IC 50 values of 45 and 100 nM, respectively.

Substituted alkylamine derivatives and methods of use

Selected amines are effective for prophylaxis and treatment of diseases, such as angiogenesis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.