1044920-98-0

Basic information

• Product Name: Methyl 4-chloro-3-formylbenzoate
• Synonyms: Methyl 4-chloro-3-formylbenzoate
• CAS NO: 1044920-98-0
• Molecular Formula: C₉H₇ClO₃
• Molecular Weight: 198.60308
• Mol File: 1044920-98-0.mol

Chemical Properties

• Boiling Point: 295.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.315±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Methyl 4-chloro-3-formylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-chloro-3-formylbenzoate(1044920-98-0)
• EPA Substance Registry System: Methyl 4-chloro-3-formylbenzoate(1044920-98-0)

Safety Data

• Hazardous Substances Data: 1044920-98-0(Hazardous Substances Data)

Upstream product

• 52178-50-4 Methyl 3-formylbenzoate 
• 91367-05-4 methyl 4-chloro-3-methylbenzoate 
• 1260675-02-2 4-chloro-3-hydroxymethylbenzoic acid methyl ester 
• 7697-29-2 4-chloro-3-methylbenzoic acid 

Downstream Products

• 651058-97-8 2-chloro-5-(methoxycarbonyl)benzoic acid 
• 884494-66-0 2-ethyl 5-methyl 1H-indole-2,5-dicarboxylate 

Relevant articles and documents

Design, synthesis, and biological evaluation of dual targeting inhibitors of histone deacetylase 6/8 and bromodomain BRPF1

Histone modifying proteins, specifically histone deacetylases (HDACs) and bromodomains, have emerged as novel promising targets for anticancer therapy. In the current work, based on available crystal structures and docking studies, we designed dual inhibitors of both HDAC6/8 and the bromodomain and PHD finger containing protein 1 (BRPF1). Biochemical and biophysical tests showed that compounds 23a,b and 37 are nanomolar inhibitors of both target proteins. Detailed structure-activity relationships were deduced for the synthesized inhibitors which were supported by extensive docking and molecular dynamics studies. Cellular testing in acute myeloid leukemia (AML) cells showed only a weak effect, most probably because of the poor permeability of the inhibitors. We also aimed to analyse the target engagement and the cellular activity of the novel inhibitors by determining the protein acetylation levels in cells by western blotting (tubulin vs histone acetylation), and by assessing their effects on various cancer cell lines.

Design, synthesis and evaluation of novel 2-(1H-imidazol-2-yl) pyridine Sorafenib derivatives as potential BRAF inhibitors and anti-tumor agents

A series of 2-(1H-imidazol-2-yl) pyridine derivatives (CLW01-CLW31) have been designed and synthesized, and they were screened for BRAF kinase inhibitory activity. Besides, their biological activities were evaluated in vitro and in vivo. All the compounds were reported for the first time, and compounds CLW14 and CLW27 displayed the most potent antiproliferative activity against cell line A375 in vitro, with IC50 values of 4.26 and 2.93 1/4M, respectively, which were comparable with the positive control Sorafenib. Those two compounds were further evaluated for the in vivo efficacy using an A375 xenograft nude mice model. The results showed that the growth of A375 cancer cells xenografts was suppressed by factors of 35.68% and 42.50% (percent tumor growth inhibition values) after intragastric (ig) administration of compound CLW14 and CLW27 at concentration of 50 mg/kg. Thus they may be promising lead compounds to be developed as an alternative for current Sorafenib therapy.

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

Diverse ortho-C(sp2)-H functionalization of benzaldehydes using transient directing groups

Pd-catalyzed C-H functionalizations promoted by transient directing groups remain largely limited to C-H arylation only. Herein, we report a diverse set of ortho-C(sp2)-H functionalizations of benzaldehyde substrates using the transient directing group strategy. Without installing any auxiliary directing group, Pd(II)-catalyzed C-H arylation, chlorination, bromination, and Ir(III)-catalyzed amidation, could be achieved on benzaldehyde substrates. The transient directing groups formed in situ via imine linkage can override other coordinating functional groups capable of directing C-H activation or catalyst poisoning, significantly expanding the scope for metal-catalyzed C-H functionalization of benzaldehydes. The utility of this approach is demonstrated through multiple applications, including late-stage diversification of a drug analogue.

Structure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity

Histone deacetylases (HDACs) are important modulators of epigenetic gene regulation and additionally control the activity of non-histone protein substrates. While for HDACs 1-3 and 6 many potent selective inhibitors have been obtained, for other subtypes much less is known on selective inhibitors and the consequences of their inhibition. The present report describes the development of substituted benzhydroxamic acids as potent and selective HDAC8 inhibitors. Docking studies using available crystal structures have been used for structure-based optimization of this series of compounds. Within this study, we have investigated the role of HDAC8 in the proliferation of cancer cells and optimized hits for potency and selectivity, both in vitro and in cell culture. The combination of structure-based design, synthesis, and in vitro screening to cellular testing resulted in potent and selective HDAC8 inhibitors that showed anti-neuroblastoma activity in cellular testing.

Novel compounds useful for bradykinin B1 receptor antagonism

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