79637-84-6

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(2,4-diaminophenyl)acetic acid is used as a precursor in the production of various drugs, such as gabapentin and pregabalin, for treating epilepsy, neuropathic pain, and anxiety disorders. Its unique structure allows it to be a key component in the development of these medications.
Used in Chelating Applications:
2-(2,4-diaminophenyl)acetic acid is used as a chelating agent for metal ion complexation. Its ability to form stable complexes with metal ions makes it a candidate for applications in environmental remediation, where it can help in the removal or recovery of heavy metals from contaminated sites.

InChI:InChI=1/C8H10N2O2/c9-6-2-1-5(3-8(11)12)7(10)4-6/h1-2,4H,3,9-10H2,(H,11,12)

Upstream product

• 643-43-6 (2,4-dinitro-phenyl)-acetic acid 

Downstream Products

• 1621584-44-8 N-(2-oxoindolin-6-ylcarbamoyl)-2-fluoro-4-methoxybenzamide 
• 1621584-43-7 N-(2-oxoindolin-6-ylcarbamoyl)-4-(dimethylamino)benzamide 
• 1621584-42-6 N-(2-oxoindolin-6-ylcarbamoyl)-3,5-dimethoxybenzamide 
• 1621584-41-5 N-(2-oxoindolin-6-ylcarbamoyl)-4-methylbenzamide 
• 1621584-40-4 N-(2-oxoindolin-6-ylcarbamoyl)-4-chloro-3-(trifluoromethyl)benzamide 
• 1621584-39-1 N-(2-oxoindolin-6-ylcarbamoyl)-4-(trifluoromethyl)benzamide 
• 1621584-38-0 N-(2-oxoindolin-6-ylcarbamoyl)-2-fluorobenzamide 
• 1621584-37-9 N-(2-oxoindolin-6-ylcarbamoyl)-3,4-dichlorobenzamide 
• 1621584-36-8 N-(2-oxoindolin-6-ylcarbamoyl)-4-chlorobenzamide 
• 1621584-35-7 N-(2-oxoindolin-6-ylcarbamoyl)benzamide 
• 1621584-34-6 N-(2-oxoindolin-6-ylcarbamoyl)-4-methoxybenzamide 
• 1474049-17-6 (E)-N-(3-(furan-2-ylmethylene)-2-oxoindolin-6-ylcarbamoyl)-4-methoxybenzamide 
• 1621584-60-8 N-(2-oxo-3-(pyridin-4-ylmethylidene)indolin-6-ylcarbamoyl)-4-methoxybenzamide 
• 1621584-59-5 N-(2-oxo-3-(pyridin-2-ylmethylidene)indolin-6-ylcarbamoyl)-4-methoxybenzamide 

Relevant academic research and scientific papers

Discovery of (Z)-1-(3-((1 H-Pyrrol-2-yl)methylene)-2-oxoindolin-6-yl)-3-(isoxazol-3-yl)urea Derivatives as Novel and Orally Highly Effective CSF-1R Inhibitors for Potential Colorectal Cancer Immunotherapy

Inhibiting the polarization or survival of tumor-associated macrophages through blocking CSF-1/CSF-1R signal transduction has become a promising strategy for cancer immunotherapy. Herein, a series of (Z)-1-(3-((1H-pyrrol-2-yl)methylene)-2-oxoindolin-6-yl)-3-(isoxazol-3-yl)urea derivatives were designed, synthesized, and evaluated as novel and orally highly effective CSF-1R inhibitors for colorectal cancer immunotherapy. Among these derivatives, compound 21 was found to possess excellent CSF-1R inhibitory activity (IC50 = 2.1 nM) and potent antiproliferative activity against colorectal cancer cells. Compound 21 inhibited the progression of colorectal cancer by suppressing the migration of macrophages, reprograming M2-like macrophages to the M1 phenotype, and enhancing the antitumor immunity. More importantly, compound 21, as a single agent, showed significantly superior in vivo anticolorectal cancer efficacy over PLX3397, highlighting a promising candidate for the immunotherapy of colorectal cancer.

Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia

A series of 6-acylureido derivatives containing a 3-(pyrrol-2- ylmethylidene)indolin-2-one scaffold were synthesized as potential dual Aurora B/FLT3 inhibitors by replacing the 6-arylureido moiety in 6-arylureidoindolin-2- one-based multi-kinase inhibitors. (Z)-N-(2-(pyrrolidin-1-yl)ethyl)-5-((6-(3-(2- fluoro-4-methoxybenzoyl)ureido)-2-oxoindolin-3-ylidene)methyl)-2, 4-dimethyl-1H-pyrrole-3-carboxamide (54) was identified as a dual Aurora B/FLT3 inhibitor (IC50 = 0.4 nM and 0.5 nM, respectively). Compound 54 also exhibited potent cytotoxicity with single-digit nanomolar IC50 values against the FLT3 mutant-associated human acute myeloid leukemia (AML) cell lines MV4-11 (FLT3-ITD) and MOLM-13 (FLT3-ITD). Compound 54 also specifically induced extrinsic apoptosis by inhibiting the phosphorylation of the Aurora B and FLT3 pathways in MOLM-13 cells. Compound 54 had a moderate pharmacokinetic profile. The mesylate salt of 54 efficiently inhibited tumor growth and reduced the mortality of BALB/c nude mice (subcutaneous xenograft model) that had been implanted with AML MOLM-13 cells. Compound 54 is more potent than sunitinib not only against FLT3-WT AML cells but also active against sunitinib-resistant FLT3-ITD AML cells. This study demonstrates the significance of dual Aurora B/FLT3 inhibitors for the development of potential agents to treat AML.

INDOLIN-2-ONE DERIVATIVES AS PROTEIN KINASE INHIBITORS

A novel class of indoline-2-one derivatives are disclosed. These compounds are protein kinase inhibitors which are useful for treating hyperproliferative diseases such as cancer.

Synthesis and structure-activity relationship of 6-arylureido-3-pyrrol-2- ylmethylideneindolin-2-one derivatives as potent receptor tyrosine kinase inhibitors

A series of new ureidoindolin-2-one derivatives were synthesized and evaluated as inhibitors of receptor tyrosine kinases. Investigation of structure-activity relationships at positions 5, 6, and 7 of the oxindole skeleton led to the identification of 6-ureido-substituted 3-pyrrolemethylidene- 2-oxindole derivatives that potently inhibited both the vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) families of receptor tyrosine kinases. Several derivatives showed potency against the PDGFR inhibiting both its enzymatic and cellular functions in the single-digit nanomolar range. Among them, compound 35 was a potent inhibitor against tyrosine kinases, including VEGFR and PDGFR families, as well as Aurora kinases. Inhibitor 36 (non-substituted on the pyrrole or phenyl ring) had a moderate pharmacokinetic profile and completely inhibited tumor growth initiated with the myeloid leukemia cell line, MV4-11, in a subcutaneous xenograft model in BALB/c nude mice.