13682-18-3

Basic information

• Product Name: 2-(3-NITRO-PHENYL)-1H-IMIDAZOLE
• Synonyms: 2-(3-NITRO-PHENYL)-1H-IMIDAZOLE;2-(3-Nitrophenyl)iMidazole
• CAS NO: 13682-18-3
• Molecular Formula: C₉H₇N₃O₂
• Molecular Weight: 189.17
• Mol File: 13682-18-3.mol

Chemical Properties

• Melting Point: 173-174 °C
• Boiling Point: 430.544 °C at 760 mmHg
• Flash Point: 214.185 °C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 3.23E-07mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.24±0.12(Predicted)
• CAS DataBase Reference: 2-(3-NITRO-PHENYL)-1H-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-NITRO-PHENYL)-1H-IMIDAZOLE(13682-18-3)
• EPA Substance Registry System: 2-(3-NITRO-PHENYL)-1H-IMIDAZOLE(13682-18-3)

Safety Data

• Hazardous Substances Data: 13682-18-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Nitro-phenyl)-1H-imidazole is used as an active pharmaceutical ingredient for its potential antibacterial and antifungal properties, making it a candidate for the development of new drugs to combat resistant infections.
Used in Material Science:
In the field of material science, 2-(3-Nitro-phenyl)-1H-imidazole may be utilized in the synthesis of new materials with specific properties, such as those with enhanced stability or reactivity, due to its unique chemical structure.
Used in Organic Synthesis:
2-(3-Nitro-phenyl)-1H-imidazole serves as a key intermediate in organic synthesis, where it can be used to construct more complex organic molecules with a variety of applications, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C9H7N3O2/c13-12(14)8-3-1-2-7(6-8)9-10-4-5-11-9/h1-6H,(H,10,11)

Upstream product

• 601494-32-0 2-(3-nitro-phenyl)-1⁽³⁾H-imidazole-4-carboxylic acid 
• 871886-13-4 2-(3-nitro-phenyl)-1H-imidazole-4,5-dicarboxylic acid 
• 98-95-3 nitrobenzene 
• 50846-98-5 2-Diazo-2H-imidazole 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 131543-46-9 Glyoxal 
• 99-61-6 3-nitro-benzaldehyde 
• 22483-09-6 2,2-dimethoxyethylamine 
• 54316-43-7 3-nitro-benzimidic acid methyl ester 
• 619-24-9 3-nitrobenzonitrile 
• 288-32-4 1H-imidazole 
• 99-09-2 3-nitro-aniline 

Downstream Products

• 1160826-42-5 C₁₆H₁₀N₄O₅ 
• 1160826-51-6 C₁₆H₁₀BrN₃O₃ 
• 1220701-14-3 2-(methylthio)-4-(2-(3-nitrophenyl)-1H-imidazol-1-yl)pyrimidine 
• 161887-05-4 3‐(1H‐Imidazol‐2‐yl)aniline 
• 1335144-95-0 C₁₅H₁₀N₄O₃ 
• 1220701-22-3 (S)-4-chloro-N-(3-(1-(2-(2-hydroxypropylamino)pyrimidin-4-yl)-1H-imidazol-2-yl)phenyl)-3-(trifluoromethyl)benzamide 
• 1220701-38-1 (S)-1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(3-(1-(2-(2-hydroxypropylamino)pyrimidin-4-yl)-1H-imidazol-2-yl)phenyl)urea 
• 1220701-20-1 (S)-1-(4-(2-(3-aminophenyl)-1H-imidazol-1-yl)pyrimidin-2-ylamino)propan-2-ol 
• 1220701-18-7 (S)-1-(4-(2-(3-nitrophenyl)-1H-imidazol-1-yl)pyrimidin2-ylamino)propan-2-ol 
• 1220701-16-5 2-(methylsulfonyl)-4-(2-(3-nitrophenyl)-1H-imidazol-1-yl)pyrimidine 
• 876343-58-7 dimethyl-{2-[2-(3-nitrophenyl)imidazol-1-yl]ethyl}amine 

Relevant articles and documents

A sustainable approach towards the three-component synthesis of unsubstituted 1H-imidazoles in the water at ambient conditions

A green protocol for the synthesis of unsubstituted imidazoles has been demonstrated herein. The reaction is realized using commercially available lipase enzyme, porcine pancreas lipase (PPL) in water. The reaction conditions are selective and mild which helped to tolerate a wide variety of functional groups to give the desired products in good chemical yields. (Figure presented.).

Diarylureas Containing 5-Membered Heterocycles as CB1 Receptor Allosteric Modulators: Design, Synthesis, and Pharmacological Evaluation

Allosteric modulators have attracted significant interest as an alternate strategy to modulate CB1 receptor signaling for therapeutic benefits that may avoid the adverse effects associated with orthosteric ligands. Here we extended our previous structure-activity relationship studies on the diarylurea-based CB1 negative allosteric modulators (NAMs) by introducing five-membered heterocycles to replace the 5-pyrrolidinylpyridinyl group in PSNCBAM-1 (1), one of the first generation CB1 allosteric modulators. Many of these compounds had comparable potency to 1 in blocking the CB1 agonist CP55,940 stimulated calcium mobilization and [35S]GTP-γ-S binding. Similar to 1, most compounds showed positive cooperativity by increasing [3H]CP55,940 binding, consistent with the positive allosteric modulator (PAM)-antagonist mechanism. Interestingly, these compounds exhibited differences in ability to increase specific binding of [3H]CP55,940 and decrease binding of the antagonist [3H]SR141716. In saturation binding studies, only increases in [3H]CP55,940 Bmax, but not Kd, were observed, suggesting that these compounds stabilize low affinity receptors into a high affinity state. Among the series, the 2-pyrrolyl analogue (13) exhibited greater potency than 1 in the [35S]GTP-γ-S binding assay and significantly enhanced the maximum binding level in the [3H]CP5,5940 binding assay, indicating greater CB1 receptor affinity and/or cooperativity.

DIARYLUREAS AS CB1 ALLOSTERIC MODULATORS

The present invention provides novel diarylurea derivatives (compounds of formula (I)) and their uses. The compounds of the present invention are demonstrated to be allosteric modulators of the CB1 receptor, and therefore useful for the treatment of diseases and conditions mediated by CB1.

IMIDAZOLE DERIVATIVES AND COMPOSITIONS FOR TREATING MELANOMA

The present invention relates to novel imidazole derivatives or pharmaceutically acceptable salts thereof, preparation methods thereof and pharmaceutical compositions for prevention and treatment of melanoma containing the same as active ingredients. The

Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones

A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (111) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (1220) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol- 1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC]=3.13 g) was equipotent as standard drug ciprofloxacin and [2-(4-Nitro-phenyl)- benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC=1.56 g) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC=0.002 g) was two times more effective than standard drug ciprofloxacin (MIC=0.004 g) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)- imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC=0.005 g) was equipotent to the reference compound, fluconazole against tested fungal strains.

Design and synthesis of 2-arylbenzimidazoles and evaluation of their inhibitory effect against Chlamydia pneumoniae

Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 μM, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 μM against CWL-029 and 6.3 μM against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.

Discovery and initial SAR of pyrimidin-4-yl-1H-imidazole derivatives with antiproliferative activity against melanoma cell lines

The synthesis of a novel series of pyrimidin-4-yl-1H-imidazol-2-yl derivatives 7, 8, 9 and their antiproliferative activities against A375P human melanoma cell line and WM3629 cell line were described. Most compounds showed superior antiproliferative activities compared to Sorafenib, the well-known RAF inhibitor. Among them, 7a exhibited potent activities on both cell lines (IC50 = 0.62 and 4.49 μM, respectively) and turned out to be a selective and potent CRAF inhibitor.

Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives

In the present study, we have synthesized 2-(substituted phenyl)-1H-imidazole (1-12) and (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanone (13-26) analogues and screened them for their antimicrobial activity against Gram positive, Gram negative and fungal species. The results of antibacterial study indicated that compounds 15, 17 and 24 showed appreciable antibacterial activity and compound 26 emerged as the most potential antifungal agent. The results of SAR studies indicated that the presence of electron withdrawing groups is necessary for the antimicrobial activity of the synthesized compounds. The results of the present study indicated that compounds 15, 17 and 24 might be of interest for the identification of new antimicrobial molecules as their antibacterial activity is equivalent to the standard drug norfloxacin. Further, the antiviral screening of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13-26) against a panel of viral strains indicated that compounds 16 and 19 can be selected as lead compounds for the development of novel antiviral agents.

A simple and convenient one-pot method for the preparation of heteroaryl-2-imidazoles from nitriles

A simple, convenient and high-yielding one-pot method for the synthesis of 2-heterocycle-substituted imidazoles from the corresponding nitriles has been developed. The procedure is easily scaleable and the workup does not involve chromatography. This synthesis is also applicable to the preparation of imidazoles with electron-poor aryl substituents.

ARYL-AMINO SUBSTITUTED PYRROLOPYRIMIDINE MULTI-KINASE INHIBITING COMPOUNDS

Compounds represented by Formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, are inhibitors of least two of the Abl, Aurora-A, Blk, c-Raf, cSRC, Src, PRK2, FGFR3, Flt3, Lck, Mekl, PDK-1, GSK3?, EGFR, p70S6K, BMX, SGK, CaMKII, Tie-2