1025909-27-6

Basic information

• Product Name: (2,4-Diamino-5-fluoro-phenyl)-acetic acid methyl ester
• Synonyms: (2,4-Diamino-5-fluoro-phenyl)-acetic acid methyl ester
• CAS NO: 1025909-27-6
• Molecular Weight: 198.197
• Mol File: 1025909-27-6.mol

Chemical Properties

• CAS DataBase Reference: (2,4-Diamino-5-fluoro-phenyl)-acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-Diamino-5-fluoro-phenyl)-acetic acid methyl ester(1025909-27-6)
• EPA Substance Registry System: (2,4-Diamino-5-fluoro-phenyl)-acetic acid methyl ester(1025909-27-6)

Safety Data

• Hazardous Substances Data: 1025909-27-6(Hazardous Substances Data)

Upstream product

• 331-25-9 (3-fluorophenyl)acetic acid 
• 150544-00-6 methyl (5-fluoro-2,4-dinitrophenyl)acetate 

Downstream Products

• 1621584-46-0 N-(5-fluoro-2-oxoindolin-6-ylcarbamoyl)-2-fluoro-4-methoxybenzamide 
• 1621584-45-9 N-(5-fluoro-2-oxoindolin-6-ylcarbamoyl)-4-methoxybenzamide 
• 150544-01-7 6-amino-5-fluoroindolin-2-one 

Relevant articles and documents

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.

IMIDAZOLE DERIVATIVES AS FUNCTIONALLY SELECTIVE ALPHA2C ADRENORECEPTOR AGONISTS

In its many embodiments, the present invention provides imidazole derivatives which are inhibitors of alPha2C adrenergic receptor agonists, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition or amelioration of one or more conditions associated with the alpha2C adrenergic receptors using such compounds or pharmaceutical compositions. Formula (I).

Preparation and alkylation of regioisomeric tetrahydrophthalimide-substituted indolin-2(3H)-ones

A series of novel regioisomeric tetrahydrophthalimide-substituted indolin-2-ones has been prepared via the Sommelet-Hauser type cyclization of appropriately substituted anilines as potential herbicides. The resultant indolin-2-ones were then regioselectively alkylated at N-1 and C-3 to give 1,3,3-trisubstituted indolin-2-ones. The most active series was also prepared by the bis-nitration of m-fluorophenylacetic acid followed by reduction and cyclization to give 6-amino-5-fluoroindolin-2-one. Elaboration to the tetrahydrophthalimide-substituted indolin-2-one was followed by C- and N-alkylation to give the desired compounds.