66315-15-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-4-methylamino-benzoic acid is used as a raw material for the synthesis of various pharmaceuticals due to its chemical properties and potential therapeutic effects. It has been studied for its potential use in the treatment of medical conditions such as cancer and inflammation, highlighting its importance in drug development.
Used in Cosmetic and Skincare Industry:
In the cosmetic and personal care sector, 3-Amino-4-methylamino-benzoic acid is utilized for its antioxidant and antimicrobial properties, making it a valuable ingredient in skincare products. Its ability to protect the skin and enhance product efficacy contributes to its widespread use in this industry.
Used in Dye Industry:
3-Amino-4-methylamino-benzoic acid is also used as a raw material in the synthesis of dyes, capitalizing on its chemical structure to create a range of colorants for various applications. Its role in this industry underscores its versatility and the breadth of its applications across different fields.

InChI:InChI=1/C8H10N2O2/c1-10-7-3-2-5(8(11)12)4-6(7)9/h2-4,10H,9H2,1H3,(H,11,12)

Upstream product

• 41263-74-5 4-(methylamino)-3-nitrobenzoic acid 
• 64-17-5 ethanol 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 456-22-4 4-Fluorobenzoic acid 
• 453-71-4 3-nitro-4-fluorobenzoic acid 

Downstream Products

• 53484-17-6 1-methyl-1H-benzo[d]imidazole-5-carboxylic acid 
• 90915-18-7 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylic acid 
• 211915-06-9 dabigatran etexilate 
• 1848337-06-3 2-[((4-[([(hexyloxy)carbonyl]amino)methanimidoyl]phenyl)amino)methyl]-1-methyl-1H-benzimidazole-5-carboxylic acid 
• 305381-67-3 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid 

Relevant academic research and scientific papers

A chemical approach for the synthesis of the DNA-binding domain of the oncoprotein MYC

We describe the first chemical synthesis of a functional mutant of the DNA binding domain of the oncoprotein MYC, using two alternative strategies which involve either one or two Native Chemical Ligations (NCLs). Both routes allowed the efficient synthesis of a miniprotein which is capable of heterodimerizing with MAX, and replicate the DNA binding of the native protein. The versatility of the reported synthetic approach enabled the straightforward preparation of MYC and Omomyc analogues, as well as fluorescently labeled derivatives.

One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides

Native chemical ligation (NCL) employing the N-methylbenzimidazolinone (MeNbz) linker readily provided the linear precursor of a 16-mer peptide that is difficult to obtain by stepwise solid-phase peptide synthesis. NCL and the workup conditions were improved toward a protocol that allows for quantitative removal of the 4-hydroxymercaptophenol additive and subsequent formation of the disulfide bridge in the NCL cocktail by oxidation in air, tolerated by the presence of tris(hydroxypropyl)phosphine.

Synthesis of a secretoglobin 3A2 type C (98–139) fragment by Dawson's native chemical ligation

A secretoglobin 3A2 type C (98–139) peptide was synthesized by native chemical ligation between 115Ile and 116Cys residues using Dawson's linker. The peptide-N-acyl-benzimidazolinone-glycine amide, a C-terminal thioesters precursor, was provided from 3-amino-4-(methylamino)benzoic acid. In addition, an N-terminal cysteine fragment, the (116–139) peptide, was prepared by ordinary Fmoc-solid phase peptide synthesis. Native chemical ligation of the (98–115) fragment with the Dawson's linker and the (116–139) peptide smoothly proceeded to give SCGB3A2 type C (98–139) peptide.

Structure-activity relationship study based on autoinducing peptide (AIP) from dog pathogen S. schleiferi

Herein, an effective protocol for solid-phase synthesis of peptide thiolactones by concomitant ring closure and cleavage from the solid support is reported. The strategy was applied for mapping the importance of the structural features in S. schleiferi AIP (5) by performing an alanine scan and truncation of this natural compound. This furnished some of the most potent inhibitors of accessory gene regulator (agr)-I in the human pathogen S. aureus reported to date.

Chemical Protein Synthesis Using a Second-Generation N-Acylurea Linker for the Preparation of Peptide-Thioester Precursors

The broad utility of native chemical ligation (NCL) in protein synthesis has fostered a search for methods that enable the efficient synthesis of C-terminal peptide-thioesters, key intermediates in NCL. We have developed an N-acylurea (Nbz) approach for the synthesis of thioester peptide precursors that efficiently undergo thiol exchange yielding thioester peptides and subsequently NCL reaction. However, the synthesis of some glycine-rich sequences revealed limitations, such as diacylated products that can not be converted into N-acylurea peptides. Here, we introduce a new N-acylurea linker bearing an o-amino(methyl)aniline (MeDbz) moiety that enables in a more robust peptide chain assembly. The generality of the approach is illustrated by the synthesis of a pentaglycine sequence under different coupling conditions including microwave heating at coupling temperatures up to 90 C, affording the unique and desired N-acyl-N′-methylacylurea (MeNbz) product. Further extension of the method allowed the synthesis of all 20 natural amino acids and their NCL reactions. The kinetic analysis of the ligations using model peptides shows the MeNbz peptide rapidly converts to arylthioesters that are efficient at NCL. Finally, we show that the new MeDbz linker can be applied to the synthesis of cysteine-rich proteins such the cyclotides Kalata B1 and MCoTI-II through a one cyclization/folding step in the ligation/folding buffer. (Chemical Equation Presented).

NOVEL ARYLALKENE DERIVATIVES AND USE THEREOF AS SELECTIVE ESTROGEN RECEPTOR MODULATORS

The invention provides novel ethylene derivatives represented by Formula I, which may be used as selective estrogen receptor modulators (SERMs) and useful in the prophylaxis and/or treatment of estrogen-dependent conditions or conditions.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Exploring the interplay of physicochemical properties, membrane permeability and giardicidal activity of some benzimidazole derivatives

This study evaluated the relationship between the physicochemical properties, membrane permeability and in vitro giardicidal activity of twenty nine benzimidazole derivatives (1-7n). The retention time data from reverse phase high performance chromatography (RP-HPLC) were used to estimate aqueous solubility and lipophilicity of these compounds. The apparent permeability was determined using Caco-2 cell monolayer. The calculation of some descriptors, such as Clog P, PSA, was performed using ACD labs software. For benzimidazole derivatives with NHCOOCH3, CH3, NH2, SH and SCH3 groups at the 2-position, a quadratic type of regression model was obtained with giardicidal activity and aqueous solubility or lipophilicity. On the other hand, giardicidal activity of 2-(trifluoromethyl)-1H-benzimidazole derivatives was influenced by lipophilicity, hydrogen bond donors and molecular volume but it was not determined by their apparent permeability in Caco-2 cell line.

Total synthesis of hypermodified epothilone analogs with potent in vitro antitumor activity

The convergent total synthesis of hypermodified epothilone analogs 1 and 2 has been achieved with the stereoselective cyclopropanation of allylic alcohol 17 and ring-closing olefin metathesis with diene 22 as the key steps. In spite of significant structural differences between these analogs and the natural epothilone scaffold, 1 and 2 are potent inducers of tubulin polymerization and inhibit the growth of human cancer cells in vitro with sub-nM IC50 values.

INHIBITORS OF HISTONE DEACETYLASE

The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.