405169-16-6

Basic information

• Product Name: 4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one
• Synonyms: 4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one;4-amino-5-fluoro-3-(5-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one;CHIR-258;Unii-I35H55G906;CHIR258 7.7G;TKI-258;4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one;CHIR-258(Dovitinib,TKI258)
• CAS NO: 405169-16-6
• Molecular Formula: C21H21FN6O
• Molecular Weight: 392.44
• EINECS: 1308068-626-2
• Product Categories: API intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 405169-16-6.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Density: 1.386
• Storage Temp.: -20°
• Solubility: Soluble in DMSO (up to 30 mg/ml).
• PKA: 9.44±0.70(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: 4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one(405169-16-6)
• EPA Substance Registry System: 4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one(405169-16-6)

Safety Data

• Hazardous Substances Data: 405169-16-6(Hazardous Substances Data)

Usage

Description

4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one is a complex organic compound with a unique molecular structure. It is characterized by the presence of various functional groups, including an amino group, a fluoro group, and a methylpiperazinyl group. 4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one has potential applications in the pharmaceutical and chemical industries due to its diverse functional groups and structural features.

Uses

Used in Pharmaceutical Industry:
4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one is used as a potential therapeutic agent for the treatment of melanoma. Its unique molecular structure allows it to target specific biological pathways involved in the development and progression of this aggressive skin cancer.
Used in Oncology Research:
4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one is used as a multitargeted tyrosine kinase inhibitor, specifically inhibiting FLT3 and c-KIT with IC50 values of 1 nM and 2 nM, respectively. Its ability to inhibit these kinases makes it a valuable tool in the development of targeted therapies for various types of cancer.
Used in Cancer Treatment:
4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one is used as a novel multi-target inhibitor for Flt3, c-Kit, FGFR1/3, VEGFR1/2/3, and PDGFRα/β. Its potent inhibition of these receptors (with IC50 values ranging from 1 nM to 27 nM) makes it a promising candidate for the development of new cancer treatments.
Used in Anticancer Drug Development:
4-Amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one is used as a receptor tyrosine kinase inhibitor that targets vascular endothelial growth factor-2, basic fibroblast growth factor-1, and platelet-derived growth factor β receptors. Its antiangiogenic effects, which include the inhibition of endothelial cell proliferation and motility, have been proposed as the mechanism by which it inhibits the growth and metastasis of hepatocellular carcinoma. It has been evaluated in clinical trials for the treatment of advanced solid tumors.

in vivo

the combination of tigatuzumab and tki258 inhibited huh-7 xenograft tumor growth [3]. tki258 reduced wm tumor progression [4].

References

1) Lee et al. (2005), In vivo target modulation and biological activity of CHIR-258, a multitargeted growth factor receptor kinase inhibitor, in colon cancer models; Clin. Cancer Res., 11 3633 2) Xin et al. (2006), CHIR-258 is efficacious in a newly developed fibroblast growth factor receptor 3-expressing orthotopic multiple myeloma model in mice; Clin. Cancer Res., 12 4908

Upstream product

• 77326-36-4 2-amino-6-fluorobenzonitrile 
• 402948-37-2 [6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetic acid ethyl ester 
• 109-01-3 1-methyl-piperazine 
• 1635-61-6 5-chloro-2-nitroaniline 
• 54998-08-2 4-(4-methylpiperazino)-1,2-diaminobenzene 
• 23491-48-7 5-(4-methylpiperazine-1-yl)-2-nitroaniline 
• 405169-16-6 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one 

Downstream Products

• 692737-80-7 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one DL-lactic acid salt 

Relevant articles and documents

LHMDS mediated tandem acylation-cyclization of 2-aminobenzenecarbonitriles with 2-benzymidazol-2-yl acetates: A short and efficient route to the synthesis of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-ones

We herein describe the discovery of a mild, one-pot tandem acylation-cyclization for the synthesis of 4-amino-3-benzimidazol-2- ylhydroquinolin-2-ones from 2-aminobenzenecarbonitriles and ethyl 2-benzimidazol-2-yl acetates.

Preparation method of dovitinib

The invention relates to a drug preparation method, in particular to a preparation method of dovitinib. A final product 4-amino-5-fluoro-3-(5-(4-methylpiperazine-1-yl)-1H- benzo[d]imidazol-2-yl) quinolone-2-(1H)-one is prepared by reacting ethyl 2-(5)-(4-methylpiperazine-1-yl)-1H-benzo[d]imidazol-2-yl) acetate with 2-amino-6-fluorobenzonitrile. The method is simple, convenient, high in safety and particularly suable for industrial production, the product yield and purity are high, and reaction conditions are mild.

TREATMENT OF MELANOMA

Methods of treating melanoma include administering a compound of Structure (I), a tautomer of the compound, a pharmaceutically acceptable salt of the compound, a pharmaceutically acceptable salt or the tautomer, or a mixture thereof to a subject. The comp