199584-07-1

Upstream product

• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 1427669-38-2 (2-Amino-4-methoxyphenyl)-3,4,5-trimethoxy-benzylamine 
• 1352638-00-6 3,4-dihydroxy-5-methoxy-N-(4-methoxy-2-nitrophenyl)benzamide 
• 926247-90-7 N-(2-amino-4-methoxyphenyl)-3,4,5-trimethoxybenzamide 
• 332015-19-7 2-(3,4,5-trimethoxyphenyl)-1H-5-methoxybenzimidazole 

Relevant academic research and scientific papers

Amino-Substituted Benzamide Derivatives as Promising Antioxidant Agents: A Combined Experimental and Computational Study

We prepared a range of N-arylbenzamides with a variable number of methoxy and hydroxy groups, bearing either amino or amino-protonated moieties, and used DPPH and FRAP assays to evaluate their antioxidant capacity. Most of the systems exhibit improved antioxidative properties relative to the reference BHT molecule in both assays. Combining results from both sets of experiments, the most promising antioxidative potential was displayed by the trihydroxy derivative 26, which we propose as a lead compound for a further optimization of the benzamide scaffold. Computational analysis helped in interpreting the observed trends and demonstrated that protonated systems are better antioxidants than their neutral counterparts, while underlying the positive influence of the electron-donating methoxy group on the antioxidant properties, thus confirming the experiments. It also revealed that the introduction of the hydroxy groups shifts the reactivity from both amide and amine groups toward this moiety and additionally enhances antioxidative features. This is particularly evident in 26H?+, which owes its pronounced reactivity to the stabilizing [O?···H-O] hydrogen bonding between the created phenoxyl radical and the two neighboring hydroxy groups. We demonstrated that its antioxidative activities are more favorable than those for analogous trihydroxy derivatives without the N-phenyl group or without the amide moiety, which strongly justifies the employed strategy in utilizing bisphenylamides in designing potent antioxidants.

Design, synthesis and biological studies of novel tubulin inhibitors

A series of compounds originally derived from the vascular endothelial growth factor receptor tyrosine kinase inhibitor, SU5416, were synthesized and evaluated. The most potent compound in this series, compound 3, which structurally resembles the potent a

Potent galloyl-based selective modulators targeting multidrug resistance associated protein 1 and P-glycoprotein

The multifactorial nature of chemotherapy failure in controlling cancer is often associated with the occurrence of multidrug resistance (MDR), a phenomenon likely related to the increased expression of members of the ATP binding cassette (ABC) transporter superfamily. In this respect, the most extensively characterized MDR transporters include ABCB1 (also known as MDR1 or P-glycoprotein) and ABCC1 (also known as MRP1) whose inhibition remains a priority to circumvent drug resistance. Herein, we report how the simple galloyl benzamide scaffold can be easily and properly decorated for the preparation of either MRP1 or P-gp highly selective inhibitors. In particular, some gallamides and pyrogallol-1-monomethyl ethers showed remarkable affinity and selectivity toward MRP1. On the other hand, trimethyl ether galloyl anilides, with few exceptions, exhibited moderate to very high and selective P-gp inhibition.

A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds

A series of dithiobenzanilide derivatives was synthesized and each compound was evaluated for its ability to reduce KCl-induced contractions of smooth muscle preparations of the guinea pig. Starting from a recent publication describing benzanilide derivatives as antispasmodic agents, structure-activity guided synthesis was performed to obtain compounds with improved spasmolytic activity. First, compounds with two amide bonds were designed and second, both amide oxygens were replaced by two sp2 sulfur atoms resulting in dithiobenzanilide derivatives. The most potent antispasmodic dithiobenzanilide 19 showed improved activity with an IC50 value of 0.4 μM. Moreover, the study also demonstrated that these active compounds were able to antagonize the effect of spasmogens like acetylcholine and phenylephrine and that the activity is not mediated by activation of ATP-dependent potassium channels (KATP-channels) or inhibition of endothelial nitric oxide synthase (eNOS).

Method for treating neoplasia by exposure to substituted 2-aryl-benzimidazole derivatives

A method for inhibiting neoplasia, particularly cancerous and precancerous lesions, by exposing the affected cells to substituted 2-aryl-benzimidazoles.