52711-92-9

Usage

Uses

Used in Chemical Industry:
(2,5-DIMETHOXYPHENYL)ACETYL CHLORIDE is used as a stain/dye for its ability to impart color to different materials. Its chemical properties make it suitable for use in creating dyes and metabolites, which can be utilized in a range of chemical processes and products.
Used in Research and Development:
In the field of research and development, (2,5-DIMETHOXYPHENYL)ACETYL CHLORIDE serves as a valuable compound for studying its properties and potential applications. Its use in this context aids in the discovery of new methods and techniques that can benefit various industries.
Used in Analytical Chemistry:
(2,5-DIMETHOXYPHENYL)ACETYL CHLORIDE can be employed as a reagent in analytical chemistry for the identification and quantification of specific substances. Its staining properties make it useful in various analytical techniques, such as chromatography and spectroscopy, to enhance the visibility and detection of certain compounds.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, (2,5-DIMETHOXYPHENYL)ACETYL CHLORIDE may also find applications in the pharmaceutical industry, potentially as an intermediate in the synthesis of various drugs or as a component in the development of new therapeutic agents. Its chemical properties could be harnessed to create novel compounds with specific medicinal properties.

InChI:InChI=1/C10H11ClO3/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3

Upstream product

• 1758-25-4 (2,5-dimethoxyphenyl)acetic acid 
• 6202-39-7 homogentisic acid methyl ester dimethyl ether 

Downstream Products

• 110554-61-5 (2,5-dimethoxy-phenyl)-acetic acid-(2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamide) 
• 2815-16-9 ent-18α-[(2,5-dimethoxy-phenyl)-acetoxy]-11,17β-dimethoxy-15β-yohimban-16α-carboxylic acid methyl ester 
• 19443-47-1 2-(2,5-Dimethoxy-phenyl)-N-(octahydro-naphthalen-4a-yl)-acetamide 
• 28033-69-4 2-(2,5-Dimethoxy-phenyl)-N-isopropyl-acetamide 
• 104554-98-5 α-bromomethyl(2,5-dimethoxybenzyl)ketone 
• 66469-86-1 ethyl (2,5-dimethoxyphenyl)acetate 
• 91289-44-0 N,N'-di-(2,5-dimethoxyphenylacetyl)-1,2-diaminoethane 
• 91289-45-1 N,N'-(2,5-dimethoxyphenylacetyl)-1,3-diaminopropane 
• 76196-44-6 χ-hydroxypropyl 2,5-dimethoxyphenylacetate 
• 7417-19-8 2-(2,5-dimethoxyphenyl)ethanol 
• 263906-73-6 1-diazo-3-(2,5-dimethoxy-phenyl)-propan-2-one 
• 740806-09-1 4-(2,5-dimethoxy-phenyl)-2-methyl-buta-2,3-dienoic acid isobutyl ester 
• 894802-86-9 4-(2,5-dimethoxy-phenyl)-3-oxo-butyric acid ethyl ester 
• 894804-07-0 JNK Inhibitor VIII 

Relevant academic research and scientific papers

Construction of the Tetracyclic Core Structure of Dysiherbols A-C

A synthetic study on the construction of the tetracyclic core structure of dysiherbols A-C is presented herein. In this synthesis, intramolecular [2 + 2] cycloaddition introduces a fused 6/4 ring system, followed by a Pd-catalyzed semipinacol rearrangement/Csp2-H arylation cascade to construct the ring C, and visible-light-mediated ring-opening of cyclopropyl silyl ether installs the tetracyclic core of dysiherbols.

Protein kinase CK-1 inhibitors as new potential drugs for amyotrophic lateral sclerosis

Amyotrophic lateral sclerosis (ALS) is a neurodegenerative disease where motor neurons in cortex, brain stem, and spinal cord die progressively, resulting in muscle wasting, paralysis, and death. Currently, effective therapies for ALS are lacking; however, identification of pathological TAR DNA-binding protein 43 (TDP-43) as the hallmark lesion in sporadic ALS suggests new therapeutic targets for pharmacological intervention. Pathological TDP-43 phosphorylation appears to drive the onset and progression of ALS and may result from upregulation of the protein kinase CK-1 in affected neurons, resulting in postranslational TDP-43 modification. Consequently, brain penetrant specific CK-1 inhibitors may provide a new therapeutic strategy for treating ALS and other TDP-43 proteinopathies. Using a chemical genetic approach, we report the discovery and further optimization of a number of potent CK-1δ inhibitors. Moreover, these small heterocyclic molecules are able to prevent TDP-43 phosphorylation in cell cultures, to increase Drosophila lifespan by reduction of TDP-43 neurotoxicity, and are predicted to cross the blood-brain barrier. Thus, N-(benzothiazolyl)-2-phenyl-acetamides are valuable drug candidates for further studies and may be a new therapeutic approach for ALS and others pathologies in which TDP-43 is involved.

Design, synthesis and evaluation of 2-amino-4-m-bromoanilino-6-arylmethyl- 7H-pyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors and antiangiogenic agents

A series of 2-amino-4-m-bromoanilino-6-benzyl pyrrolo[2,3-d]pyrimidines analogues 4-12 were synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). These analogues were synthesized from the appropriate α-bromomethylbenzylketones via cyclocondensation with 2,6-diamino-4- pyrimidone to afford the 2-amino-4-oxo-6-substituted benzyl pyrrolo[2,3-d] pyrimidines. Chlorination at the 4-position followed by displacement with 3-bromoaniline or 3-bromo-N-methylaniline and methylation of the 7-NH afforded the target compounds. Remarkably, dimethylation of both the 4-N and N7 afford whole cell EGFR inhibitors that are more cytotoxic than clinically used erlotinib and mono-methylation at the 4-N or N7 affords more cytotoxic whole cell PDGFR-β inhibitors than clinically used sunitinib. Methylation at either the 4-N or N7 position was detrimental to whole cell VEGFR-2 inhibition. The inhibitory data against the RTKs in this study demonstrates that methylation of the 4-NH and/or the 7-NH influences both the specificity and potency of RTK inhibition.

7-Sulfonamido-3-benzazepines as potent and selective 5-HT2C receptor agonists: Hit-to-lead optimization

New 7-sulfonamido-3-benzazepines 3 are disclosed as 5-HT2C receptor agonists. Appropriate substitution of the amino group (R1R2N-) gave compounds that were potent 5-HT2C agonists with minimal activation of the 5-HT2A and 5-HT2B receptors. Furthermore, representative examples had excellent in vitro ADME properties and good selectivity over ion channel activity.

Modulation of luminescence intensity of lanthanide complexes by photoinduced electron transfer and its application to a long-lived protease probe

Luminescent lanthanide complexes (Tb3+, Eu3+, etc.) have excellent properties for biological applications, including extraordinarily long lifetimes and large Stokes shifts. However, there have been few reports of lanthanide-based functional probes, because of the difficulty in designing suitable complexes with a luminescent on/off switch. Here, we have synthesized a series of complexes which consist of three moieties: a lanthanide chelate, an antenna, and a luminescence off/on switch. The antenna is an aromatic ring which absorbs light and transmits its energy to the metal, and the switch is a benzene derivative with a different HOMO level. If the HOMO level is higher than a certain threshold, the complex emits no luminescence at all, which indicates that the lanthanide luminescence can be modulated by photoinduced electron transfer (PeT) from the switch to the sensitizer. This approach to control lanthanide luminescence makes possible the rational design of functional lanthanide complexes, in which the luminescence property is altered by a biological reaction. To exemplify the utility of our approach to the design of lanthanide complexes with a switch, we have developed a novel protease probe, which undergoes a significant change in luminescence intensity upon enzymatic cleavage of the substrate peptide. This probe, combined with time-resolved measurements, was confirmed in model experiments to be useful for the screening of inhibitors, as well as for clinical diagnosis.

Aminopyridine-based c-Jun N-terminal kinase inhibitors with cellular activity and minimal cross-kinase activity

The c-Jun N-terminal kinases (JNK-1, -2, and -3) are members of the mitogen activated protein (MAP) kinase family of enzymes. They are activated in response to certain cytokines, as well as by cellular stresses including chemotoxins, peroxides, and irradiation. They have been implicated in the pathology of a variety of different diseases with an inflammatory component including asthma, stroke, Alzheimer's disease, and type 2 diabetes mellitus. In this work, high-throughput screening identified a JNK inhibitor with an excellent kinase selectivity profile. Using X-ray crystallography and biochemical screening to guide our lead optimization, we prepared compounds with inhibitory potencies in the low-double-digit nanomolar range, activity in whole cells, and pharmacokinetics suitable for in vivo use. The new compounds were over 1000-fold selective for JNK-1 and -2 over other MAP kinases including ERK2, p38α, and p38δ and showed little inhibitory activity against a panel of 74 kinases.

Inhibitors of c-Jun N-terminal kinases

The present invention relates to compounds that are inhibitors of c-jun N-terminal kinase 1, 2, or 3 (JNK1, JNK2, or JNK3), compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by the activation of JNK1, JNK2 and JNK3.

Antiangiogenic and antitumor agents: Design, synthesis, and evaluation of novel 2-amino-4-(3-bromoanilino)-6-benzylsubstituted pyrrolo[2,3-d]pyrimidines as inhibitors of receptor tyrosine kinases

Several different classes of growth factor receptors containing tyrosine kinases (RTK) are directly or indirectly involved in angiogenesis. Inhibition of these RTKs has provided a new paradigm in the treatment of tumors by restricting their growth and metastasis. We have designed, synthesized and evaluated eleven novel 2-amino-4-(3-bromoanilino)-6-substituted benzyl pyrrolo[2,3-d]pyrimidines as the first in a series of RTK inhibitors. These analogues were synthesized from appropriate α-bromomethylbenzyl ketones by cyclocondensation with 2,6-diamino-4-pyrimidone to afford the 2-amino-4-oxo-6-substituted benzyl pyrrolo[2,3-d]pyrimidines. Chlorination of the 4-position followed by displacement with 3-bromoaniline afforded the target compounds. In some instances, the 2-amino moiety of the pyrrolo[2,3-d] pyrimidines was protected prior to the chlorination and displacement followed by deprotection. The compounds were evaluated as inhibitors of vascular endothelial growth factor receptors VEGFR-2 (Flk-1, KDR) and VEGFR-1 (Flt-1); epidermal growth factor receptor (EGFR); and platelet-derived growth factor receptor-β (PDGFR-β). Selected compounds were also evaluated against the growth of A431 cells (which overexpress EGFR) in culture and as inhibitors of angiogenesis in the chicken embryo chorioallantonic membrane (CAM) assay. In each evaluation, a known standard compound was used as a comparison. Of the 11 analogues, five were more potent or equipotent as compared to standard compounds against the growth factor receptors. Two analogues showed superior inhibition of A431 cells in culture compared to the standard compounds. Three analogues were equipotent with the standard compound in the CAM assay and four of the analogues were dual inhibitors of RTKs. The structure-activity relationship for inhibition of different RTKs was quite distinct and different, and for VEGFR-2 and EGFR diametrically opposite. The inhibitory data against the RTKs in this study demonstrates that variation of the substituent(s) in the benzyl ring of these 2-amino-4-anilino 6-benzyl pyrrolo[2,3-d]pyrimidines does indeed control both the potency and specificity of inhibitory activity against RTKs.

N-acyl sulfamic acid esters (or thioesters), N-acyl sulfonamides, and N-sulfonyl carbamic acid esters (or thioesters) as hypercholesterolemic agents

The present invention is directed to compounds useful for the regulation of cholesterol of Formula I, methods for using them and pharmaceutical compositions thereof, STR1 wherein X and Y are oxygen, sulfur, or (CR'R")n wherein n is 1 to 4; R is hydrogen, alkyl, or benzyl; R1 and R2 are phenyl, substituted phenyl, naphthyl, substituted naphthyl, an aralkyl group, an alkyl chain, adamantyl, or a cycloalkyl group.

Synthesis of a Hexahydro-2H-imidazoisoquinolin-2-one Derivative as an Isostere of Catecholamine-based Selective Dopamine D-1 Antagonists

The synthesis of the racemic hexahydro-2H-imidazoisoquinolin-2-one 15 (BW2247W94), a 6,7-ureylene isostere of the 6,7-dihydroxy-tetrahydroisoquinoline 1 (BW32C73), has been achieved in ten stages from 4-nitrobenzyl cyanide 5.The key step is a selective reduction of the nitrile 8 to the amine 9, in the presence of nitro and carbamate functional groups.