34547-25-6

Usage

Uses

Used in Pharmaceutical Research:
2-(3,4,5-Trimethoxyphenyl)acetohydrazide is used as a research compound for exploring its potential bioactive properties and pharmacological activities. Its unique structure allows it to be a promising candidate for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
2-(3,4,5-Trimethoxyphenyl)acetohydrazide is used as a valuable intermediate in the synthesis of other organic compounds with potential pharmaceutical or biological activities. Its versatile structure and functional groups make it suitable for various synthetic routes and reactions, contributing to the development of novel compounds with desired properties.
Used in Medicinal Chemistry Applications:
2-(3,4,5-Trimethoxyphenyl)acetohydrazide is used as a building block in medicinal chemistry for the design and synthesis of new drug candidates. Its hydrazide functional group and methoxy-substituted phenyl ring provide opportunities for further functionalization and optimization of the compound's pharmacological properties, making it a valuable tool in the discovery of new therapeutic agents.

Upstream product

• 39053-78-6 3,4,5-trimethoxyphenylacetyl chloride 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 2989-06-2 methyl 2-(3,4,5-trimethoxyphenyl)acetate 
• 66162-60-5 (3,4,5-trimethoxyphenyl)acetic acid ethyl ester 

Downstream Products

• 137206-47-4 3-(3,4,5-trimethoxyphenylmethyl)-5-(3,4,5-trimethoxyphenyl)-1,2,4-triazole 
• 137206-46-3 bis-3,5-(3,4,5-trimethoxyphenylmethyl)-1,2,4-triazole 
• 1198210-19-3 4-amino-3-[(3,4,5-trimethoxyphenyl)methyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione 
• 1321976-04-8 C₂₇H₄₁N₃O₉ 
• 1321975-89-6 (S)-4-biphenyl-4-ylcarboxamido-4-(5-(3,4,5-trimethoxybenzyl)-1,3,4-oxadiazol-2-yl)butanoic acid 
• 1321976-50-4 C₃₅H₃₉N₃O₇ 
• 1321976-35-5 C₂₂H₃₁N₃O₆ 
• 1321976-17-3 C₂₇H₃₉N₃O₈ 
• 137206-52-1 (3,4,5-Trimethoxy-phenyl)-acetic acid N'-[imino-(3,4,5-trimethoxy-phenyl)-methyl]-hydrazide 
• 137206-50-9 3,4,5-trimethoxyphenylmethyl-β-3,4,5-trimethoxyphenylacetylamidrazone 
• 34546-93-5 5-(3,4,5-trimethoxy-benzyl)-3H-[1,3,4]oxadiazol-2-one 

Relevant academic research and scientific papers

Conformation impacts on the bioactivities of SMART analogues

As promising colchicine binding site inhibitors, SMART and its analogues have attracted many research efforts in recent years. A large number of SMART analogues with different B-rings have been reported; however, the effects of B-ring on the bioactivity are still unclear so far. Herein, we speculated that the conformational preference caused by B-rings was crucial for active SMART analogues. Our assumption was supported by the molecular docking studies, molecular dynamic simulation and DFT computations of SMART and its analogues reported by other and our research groups. Moreover, several novel SMART analogues with different conformational preferences were designed and synthesized to disclose the conformation impacts, and the preliminary biological evaluation was in accordance with our assumption.

Hybrid Pharmacophore Design, Molecular Docking, Synthesis, and Biological Evaluation of Novel Aldimine-Type Schiff Base Derivatives as Tubulin Polymerization Inhibitor

A series of hybrid aldimine-type Schiff base derivatives including trimethoxyphenyl ring and 1,2,4-triazole-3-thiol/thione were designed as tubulin inhibitors. The molecular docking simulations on tubulin complex (PDB: 1SA0) revealed that derivatives with nitro and/or chloro or dimethylamino substitutes (4-nitro, 2-nitro, 3-nitro, 4-Cl-3-nitro, and 4-Me2N) on the aldehyde ring were the best compounds with remarkable binding energies (?9.09, ?9.07, ?8.63, ?8.11, and ?8.07 kcal mol?1, respectively) compared to colchicine (?8.12 kcal mol?1). These compounds were also showed remarkable binding energies from ?10.66 to ?9.79 and ?10.12 to ?8.95 kcal mol?1 on human (PDB: 1PD8) and Candida albicans (PDB: 3QLS) DHFR, respectively. The obtained results of cytotoxic activities against HT1080, HepG2, HT29, MCF-7, and A549 cancer cell lines indicated that 4-nitro and 2-nitro substituted compounds were the most effective agents by mean IC50 values of 11.84 ± 1.01 and 19.92 ± 1.36 μm, respectively. 4-Nitro substituted compound (5 μm) and 2-nitro substituted compound (30 μm) were able to strongly inhibit the tubulin polymerization compared to colchicine (5 μm) and 4-nitro substituted compound displayed IC50 values of 0.16 ± 0.01 μm compared to that of colchicine (0.19 ± 0.01 μm). This compound also showed the lowest MIC values on all tested microbial strains including three Gram-positive, four Gram-negative, and three yeast pathogens.

Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone-phenol rearrangement to provide the corresponding quinolone-phenol in high yield.