50606-35-4

Usage

Uses

Used in Pharmaceutical Industry:
3,4,5-Trimethoxybenzoylacetonitrile is utilized as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and reactivity contribute to the development of new drugs and therapeutic agents.
Used in Organic Chemistry Research:
In the field of organic chemistry, 3,4,5-Trimethoxybenzoylacetonitrile is employed for its potential applications in the development of new reactions and methods. It aids in the synthesis of biologically active molecules, further expanding the horizons of chemical research and innovation.

InChI:InChI=1/C12H13NO4/c1-15-10-6-8(9(14)4-5-13)7-11(16-2)12(10)17-3/h6-7H,4H2,1-3H3

Upstream product

• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 75-05-8 acetonitrile 
• 6178-44-5 ethyl 3,4,5-trimethoxybenzoate 
• 118779-14-9 N-methoxy-N-methyl-3,4,5-trimethoxybenzamide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 118-41-2 Eudesmic acid 

Downstream Products

• 222056-46-4 2-(2,2-diethoxy-ethyl)-5-(3,4,5-trimethoxy-phenyl)-2H-pyrazol-3-ylamine 
• 901118-48-7 2-(3,4,5-trimethoxybenzoyl)-3-phenylbut-2-enenitrile 
• 76088-45-4 2-(3,4,5-trimethoxyphenyl)benzo[d]thiazol 
• 1537900-86-9 1,5-bis(3,4,5-trimethoxyphenyl)-1,2,3-triazole-4-carbonitrile 
• 1537900-92-7 1-(3-chlorophenyl)-5-(3,4,5-trimethoxyphenyl)-1,2,3-triazole-4-carbonitrile 
• 1537900-88-1 1-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,2,3-triazole-4-carbonitrile 
• 1372720-43-8 (E)-methyl 5'-(2-cyano-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-en-1-yl)-7,7'-dimethoxy-(4,4'-bibenzo[d][1,3]dioxole)-5-carboxylate 
• 1265047-94-6 (2-amino-4-(4-methoxyphenyl)thiophen-3-yl)(3,4,5-trimethoxyphenyl)methanone 

Relevant academic research and scientific papers

Synthesis and antiproliferative activity of 2-aryl-4-(3,4,5-trimethoxybenzoyl)-1,2,3-triazol derivatives as microtubule-destabilizing agents

A series of 2-aryl-4-(3,4,5-trimethoxybenzoyl)-1,2,3-triazols were designed as analogs of substituted methoxybenzoyl-aryl-thiazole (SMART) under the consideration of geometric features. The target compounds were synthesized via concise and efficient processes including microwave-assisted cyclization, and were evaluated for their antiproliferative activity against three human cancer cell lines. Most compounds exhibited moderate antiproliferative activity with IC50 values in the micromolar to sub-micromolar range. Tubulin polymerization and immunofluorescence studies demonstrated that (Z)-9a was a potent microtubule-destabilizing agent and disrupted the polymerization dynamics. Moreover, (Z)-9a significantly induced accumulation of cells in the G2/M phase and caused microtubule destabilization. Molecular modeling studies showed that (Z)-9a probably binds to the colchicine site of tubulin.

Design, synthesis and bio-evaluation of novel 2-aryl-4-(3,4,5-trimethoxy-benzoyl)-5-substituted-1,2,3-triazoles as the tubulin polymerization inhibitors

A series of 2-aryl-4-(3,4,5-trimethoxybenzoyl)-5-substituted-1,2,3-triazoles were designed, synthesized and evaluated for the anticancer activities. Based on the model of DMAM-colchicine-tubulin complex interactions, various saturated nitrogen-containing heterocycles were introduced to the C5-position of 1,2,3-triazol to interact with a tolerant region at the entrance of the binding-pocket and increase the aqueous solubility of the compounds. All designed compounds were concisely synthesized by one-pot oxidative cyclization. Most compounds exhibited moderate antiproliferative activity with IC50 values in the micromolar to sub-micromolar range. Among them, 5g posed N-acyl-piperazine moiety at the C5-position of B-ring showed most potent against cancer cells, with IC50 values of 0.084–0.221 μM 5g potently disrupted microtubule/tubulin dynamics, induced cell cycle arrest at G2/M phase in SGC-7901 cells. In addition, molecular modeling studies suggested that 5g probably binds to the colchicine site of tubulin.

3,5-Diaryl-1H-pyrazolo[3,4-b]pyridines as potent tubulin polymerization inhibitors: Rational design, synthesis and biological evaluation

A series of novel 3,5-diaryl-1H-pyrazolo[3,4-b]pyridines as tubulin polymerization inhibitors targeting the colchicine site were designed via ring tethering strategy, which was supported by conformational analysis. The general, chemically unstable and rot

Design, synthesis and biological evaluation of a novel tubulin inhibitor 7a3 targeting the colchicine binding site

Tubulin inhibitors that target the colchicine binding site continue to emerge as promising anticancer agents. In this study, based on the anti-proliferative activities, a novel tubulin inhibitor 7a3 targeting the colchicine binding site was designed, synthesized, and optimized from a series of novel cis-restricted pyrazole analogues of combretastatin A-4. The structure-activity relationships (SARs) of these newly synthesized compounds are summarized indicating that the methyl substituent at the N1 position and deamination were significantly important for the anti-proliferative efficacy. The optimized compound 7a3 exhibited the ability to arrest the cell cycle in the G2/M phase, induce cell apoptosis, and inhibit cell migration in tumour cells. The results of the immunofluorescence analysis using confocal microscopy and the tubulin polymerization assay revealed that tubulin assembly was disrupted by 7a3 in vitro. Furthermore, the targeting identification of 7a3 was illuminated by solving the crystal structure of 7a3 in complex with tubulin at a resolution of 3.2 ? (PDB code 5Z4U), which confirmed the result of molecular docking and further demonstrated that 7a3 binds to the site of colchicine. Moreover, the pharmacokinetic analysis in mouse plasma showed that 7a3 rapidly reached a peak concentration at 0.25 h after intraperitoneal administration, and the T1/2, Cmax, and AUC0-inf were 1.67 ± 0.28 h, 882 ± 71 ng mL-1, and 1166 ± 129 h ng·mL-1, respectively, after a single-dose administration analysed by liquid chromatography-tandem mass spectrometry (LC/MS/MS). In addition, the in vivo study indicated that 7a3 significantly inhibited the tumour growth of the SK-OV-3 xenograft in a nude mouse model. In conclusion, our study proved 7a3 to be a potential microtubule-targeting drug for cancer therapy. The SARs and mechanism of action studies of 7a3 based on the X-ray co-crystal structure provided insights into the next-generation tubulin inhibitors for cancer therapy.

Microtubule inhibitor as well as preparation method and application thereof

The invention relates to a microtubule inhibitor as well as a preparation method and application thereof, belongs to the field of chemical medicines and aims to solve the problem that the biological activity is rapidly reduced because the existing microtubule inhibitor CA-4 cisoid conformation is easily transformed into trans-conformation. The technical scheme provides a compound expressed by a formula I as well as pharmaceutically acceptable salts or crystals thereof. Experiment results show that the compound shows extremely strong in-vitro anti-proliferation activity in tumor cells such as ovarian cancer cells, cervical cancer cells, non-small cell lung cancer cells, colon cancer cells and breast cancer cells, can obviously inhibit the tumor progression in the body, and is high in safety; the formula I is as shown in the description.

(E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl)acetohydrazonoyl cyanides as tubulin polymerization inhibitors: Structure-based bioisosterism design, synthesis, biological evaluation, molecular docking and in silico ADME prediction

A series of (E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl)acetohydrazonoyl cyanides have been synthesized and evaluated for their anticancer activity in human hepatocellular liver carcinoma HepG2 and breast adenocarcinoma MCF-7 cell lines. Among all the test

Synthesis and biological evaluation of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone derivatives as tubulin inhibitors

A series of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanones (8a-p, 9a-p) and ketoxime (10c) derivatives were designed and synthesized as antitubulin agents. All of the target compounds were evaluated for the in vitro anti-proliferative activities against three tumor cell lines (A549, HT-1080, SGC-7901). The most promising compounds in this class were (1-(p-tolyl)-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone (9c) and its ketoxime derivative (10c), which significantly inhibited tumor cells growth with IC50 value of 0.054–0.16 μM. Meanwhile, compound 9c exhibited effectively inhibitory activity of tubulin polymerization. Consistent with its antitubulin activity, compound 9c could destructively damage microtubule network and arrest SGC-7901 cell cycle at G2/M phase significantly. The structure-activity relationship (SAR) and conformational analysis indicate that methyl group at C4-position of C-ring is critical for the activities and the amino group at the C5-position of B-ring plays a negative role in maintaining bioactivity. Furthermore, a molecular docking study was performed to elucidate its binding mode at the colchicine site in the tubulin heterodimer.

(1-aryl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and application thereof

The invention belongs to the technical field of medicines and relates to (1-aryl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and an application thereof and exactly relates to the compounds and an application thereof to antitumor medicines as tumor cell proliferation inhibitors. A structure of the compounds is shown in a general formula I in the specification: the definition of each substituent is shown in the claim and specification.

2-aryl-4-aroyl-triazole compound and application thereof

The invention belongs to the technical field of medicine, and relates to a 2-aryl-4-aroyl-triazole compound and application of the 2-aryl-4-aroyl-triazole compound, in particular to a 2-aryl-4-aroyl-triazole compound and application of the compound used as a tumor cell proliferation inhibitor in preparation of anti-tumor medicine. The structural general formula of the compound is shown as follows, wherein definitions of substituent groups are shown in the description and specification.

Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides

A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is