380567-18-0

Basic information

• Product Name: Benzoic acid, 4-[(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)methyl]-, methyl ester
• CAS NO: 380567-18-0
• Molecular Formula: C17H13NO4
• Molecular Weight: 295.295
• Mol File: 380567-18-0.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-[(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)methyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-[(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)methyl]-, methyl ester(380567-18-0)
• EPA Substance Registry System: Benzoic acid, 4-[(2,3-dihydro-2,3-dioxo-1H-indol-1-yl)methyl]-, methyl ester(380567-18-0)

Safety Data

• Hazardous Substances Data: 380567-18-0(Hazardous Substances Data)

Upstream product

• 91-56-5 indole-2,3-dione 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 99-94-5 p-Toluic acid 

Downstream Products

• 1380087-59-1 1,1'-bis(4-methoxycarbonylbenzyl)-3,3'-biindolinylidene-2,2'-dione 

Relevant articles and documents

Design, synthesis and evaluation of novel indirubin-based N-hydroxybenzamides, N-hydroxypropenamides and N-hydroxyheptanamides as histone deacetylase inhibitors and antitumor agents

Several novel indirubin-based N-hydroxybenzamides, N-hydropropenamides and N-hydroxyheptanamides (4a-h, 7a-h, 10a-h) were designed using a fragment-based approach with structural features extracted from several previously reported HDAC inhibitors, such as

Novel quinolone-based potent and selective HDAC6 inhibitors: Synthesis, molecular modeling studies and biological investigation

In this work we describe the synthesis of potent and selective quinolone-based histone deacetylase 6 (HDAC6) inhibitors. The quinolone moiety has been exploited as an innovative bioactive cap-group for HDAC6 inhibition; its synthesis was achieved by applying a multicomponent reaction. The optimization of potency and selectivity of these products was performed by employing computational studies which led to the discovery of the diethylaminomethyl derivatives 7g and 7k as the most promising hit molecules. These compounds were investigated in cellular studies to evaluate their anticancer effect against colon (HCT-116) and histiocytic lymphoma (U9347) cancer cells, showing good to excellent potency, leading to tumor cell death by apoptosis induction. The small molecules 7a, 7g and 7k were able to strongly inhibit the cytoplasmic and slightly the nuclear HDAC enzymes, increasing the acetylation of tubulin and of the lysine 9 and 14 of histone 3, respectively. Compound 7g was also able to increase Hsp90 acetylation levels in HCT-116 cells, thus further supporting its HDAC6 inhibitory profile. Cytotoxicity and mutagenicity assays of these molecules showed a safe profile; moreover, the HPLC analysis of compound 7k revealed good solubility and stability profile.

Novel Indirubin-based N-Hydroxybenzamides, N-Hydroxypropenamides and N-Hydroxyheptanamides and its use

The present invention relates to novel indirubin-based N-hydroxybenzamide, N-hydroxypropanamide and N-hydroxyheptanamide compounds as histone deacetylase (HDAC) inhibitors, and an anticancer composition comprising the same as an active component. More specifically, the compound according to the present invention has strong HDAC inhibitory activity, thereby being able to be used as a proliferation inhibitor for various cancer cells. Therefore, it is expected that the compound according to the present invention can be developed as an active component of a powerful anticancer agent.

1-benzylisatin derivative as well as synthesis method and application thereof

The invention relates to a 1-benzylisatin derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituents. The invention discloses structures of the compounds, a synthesis method of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activityof histone deacetylase 6; and the compounds can be further developed into drugs for treating Alzheimer's disease.

Novel N-hydroxybenzamide and Use Thereof

The present invention relates to a novel N-hydroxybenzamide and to uses thereof. More specifically, the present invention provides the novel N-hydroxybenzamide-based compound useful as histone deacetylase inhibitors, and compositions comprising the same, wherein the compound according to the present invention is useful as a medicine for treatment and prevention of cancer.COPYRIGHT KIPO 2018

X-ray crystallographic study of diversely substituted isatin derivatives

A series of isatin derivatives were synthesized and studied by XRD. For the first time the peculiarities of the molecule structure and crystal packing effects were analyzed. Indoline heterocycles are planar in all the investigated structures. The molecule

Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents

Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies.

USE OF SPIRO-OXINDOLE COMPOUNDS AS THERAPEUTIC AGENTS

This invention is directed to methods of using spiro-oxindole compounds of formula (I): wherein k, j, Q, R1, R2a, R2b, R2c, R2d, R3a, R3b, R3c, and R3d are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of hypercholesterolemia, benign prostatic hyperplasia, pruritis and cancer.

OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS

This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.