221640-38-6

Basic information

• Product Name: [4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE
• Synonyms: [4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE
• CAS NO: 221640-38-6
• Molecular Formula: C₁₁H₁₃N₃
• Molecular Weight: 187.24102
• Mol File: 221640-38-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: [4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE(221640-38-6)
• EPA Substance Registry System: [4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE(221640-38-6)

Safety Data

• Hazardous Substances Data: 221640-38-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
[4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE is used as a building block for the synthesis of various drugs and bioactive molecules. Its chemical structure allows for the creation of a wide range of pharmaceutical compounds, contributing to the development of new treatments and therapies.
Used in Organic Chemistry Reactions:
[4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE serves as a reagent in organic chemistry, facilitating various chemical reactions and transformations. Its presence can enhance the efficiency and selectivity of these reactions, making it a valuable asset in the synthesis of complex organic molecules.
Used in Dye and Pigment Manufacturing:
[4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE is also utilized as a precursor in the manufacture of certain dyes and pigments. Its unique chemical properties enable the production of a variety of colorants used in different industries, such as textiles, plastics, and printing inks.
Used in Chemical Synthesis Industry:
In the chemical synthesis industry, [4-(1H-IMIDAZOL-2-YL)-PHENYL]-DIMETHYL-AMINE is used as a versatile intermediate for the production of a diverse array of chemical products. Its ability to participate in various chemical reactions makes it a key component in the synthesis of specialty chemicals and materials.

Upstream product

• 107-15-3 ethylenediamine 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 131543-46-9 Glyoxal 

Downstream Products

• 1253697-55-0 N,N-dimethyl-4-(1-(phenylsulfonyl)-1H-imidazol-2-yl)aniline 
• 1332526-29-0 4-(1-((4-methoxyphenyl)sulfonyl)-1H-imidazol-2-yl)-N,N-dimethylaniline 
• 1332526-31-4 (2-(4-(dimethylamino)phenyl)-1-((4-methoxyphenyl)sulfonyl)-1H-imidazol-4-yl)(4-fluorophenyl)methanone 

Relevant articles and documents

COMPOUNDS FOR TREATMENT OF CANCER

The present invention relates to pharmaceutical compositions for treating cancer comprising BRAF inhibitors, (e.g. vemurafenib) and/or MEK inhibitor, (e.g. trametinib, RO5068760), in combination with anti-tubulin compounds of the invention or other known tubulin inhibitors, and using such compositions for treating cancer such as melanoma, drug-resistant cancer, and cancer metastasis.

An efficient and convenient synthesis of imidazolines and benzimidazoles via oxidation of carbon-nitrogen bond in water media

The metal coordination complex K4[Fe(CN)6] is an efficient and environmentally benign catalyst for the synthesis of imidazolines and benzimidazoles from various aldehydes and 1,2-diamines in aqueous medium at room temperature. This protocol gives excellent yield of product with desired purity. Copyright

COMPOUNDS FOR TREATMENT OF CANCER

The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.

Synthesis and antiproliferative activity of novel 2-aryl-4-benzoyl- imidazole derivatives targeting tubulin polymerization

We previously reported the discovery of 2-aryl-4-benzoyl-imidazoles (ABI-I) as potent antiproliferative agents for melanoma. To further understand the structural requirements for the potency of ABI analogs, gain insight in the structure-activity relationships (SAR), and investigate metabolic stability for these compounds, we report extensive SAR studies on the ABI-I scaffold. Compared with the previous set of ABI-I analogs, the newly synthesized ABI-II analogs have lower potency in general, but some of the new analogs have comparable potency to the most active compounds in the previous set when tested in two melanoma and four prostate cancer cell lines. These SAR studies indicated that the antiproliferative activity was very sensitive to subtle changes in the ligand. Tested compounds 3ab and 8a are equally active against highly paclitaxel resistant cancer cell lines and their parental cell lines, indicating that drugs developed based on ABI-I analogs may have therapeutic advantages over paclitaxel in treating resistant tumors. Metabolic stability studies of compound 3ab revealed that N-methyl imidazole failed to extend stability as literature reported because de-methylation was found as the major metabolic pathway in rat and mouse liver microsomes. However, this sheds light on the possibility for many modifications on imidazole ring for further lead optimization since the modification on imidazole, such as compound 3ab, did not impact the potency.

Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents

A series of 2-aryl-4-benzoyl-imidazoles (ABI) was synthesized as a result of structural modifications based on the previous set of 2-aryl-imidazole-4- carboxylic amide (AICA) derivatives and 4-substituted methoxylbenzoyl-aryl- thiazoles (SMART). The average IC50 of the most active compound (5da) was 15.7 nM. ABI analogues have substantially improved aqueous solubility (48.9 μg/mL for 5ga vs 0.909 μg/mL for SMART-1, 0.137 μg/mL for paclitaxel, and 1.04 μg/mL for combretastatin A4). Mechanism of action studies indicate that the anticancer activity of ABI analogues is through inhibition of tubulin polymerization by interacting with the colchicine binding site. Unlike paclitaxel and colchicine, the ABI compounds were equally potent against multidrug resistant cancer cells and the sensitive parental melanoma cancer cells. In vivo results indicated that 5cb was more effective than DTIC in inhibiting melanoma xenograph tumor growth. Our results suggest that the novel ABI compounds may be developed to effectively treat drug-resistant tumors.