124068-97-9

Basic information

• Product Name: 4-NITRO-PHENYL-N-BENZYLCARBAMATE
• Synonyms: 4-Nitrophenyl N-Benzylcarbamate;4-Nitrophenyl benzylcarbamate
• CAS NO: 124068-97-9
• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.26
• Mol File: 124068-97-9.mol

Chemical Properties

• Melting Point: 130.0 to 134.0 °C
• Boiling Point: 436.1°Cat760mmHg
• Flash Point: 217.5°C
• Appearance: /
• Density: 1.306g/cm³
• Vapor Pressure: 8.32E-08mmHg at 25°C
• Refractive Index: 1.609
• PKA: 10.54±0.46(Predicted)
• BRN: 4261736
• CAS DataBase Reference: 4-NITRO-PHENYL-N-BENZYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-PHENYL-N-BENZYLCARBAMATE(124068-97-9)
• EPA Substance Registry System: 4-NITRO-PHENYL-N-BENZYLCARBAMATE(124068-97-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 124068-97-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-NITRO-PHENYL-N-BENZYLCARBAMATE is used as a reactant for the preparation of radiofluorinated quinoxalinedione derivatives, which are potential ligands of the AMPA receptor. These ligands are important for studying the function and modulation of AMPA receptors, which play a crucial role in neurological processes and are implicated in various neurological disorders.
Used in Peptide Synthesis:
In the field of peptide synthesis, 4-NITRO-PHENYL-N-BENZYLCARBAMATE is utilized as a reactant for the preparation of mono-substituted urea side chains in solid phase peptide synthesis. This application is significant for the development of novel peptides with specific biological activities and potential therapeutic applications.
Used in Organic Synthesis:
4-NITRO-PHENYL-N-BENZYLCARBAMATE is also used as a reactant for the synthesis of 4-substituted-1,2,4-triazolidine-3,5-diones. These compounds are of interest in organic chemistry due to their unique structural features and potential applications in various chemical transformations.
Used in Enzyme Inhibition Studies:
Furthermore, 4-NITRO-PHENYL-N-BENZYLCARBAMATE is employed in the preparation of aryl carbamates, which serve as probes for understanding the inhibition mechanism of cholesterol esterase. This enzyme plays a key role in lipid metabolism, and its inhibition can have implications in the treatment of various metabolic disorders and diseases.

InChI:InChI=1/C14H12N2O4/c17-14(15-10-11-4-2-1-3-5-11)20-13-8-6-12(7-9-13)16(18)19/h1-9H,10H2,(H,15,17)

Upstream product

• 50780-50-2 4-chloromethoxycarbonyloxy-1-nitrobenzene 
• 100-46-9 benzylamine 
• 100-02-7 4-nitro-phenol 
• 3173-56-6 benzyl isothiocyanate 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 3287-99-8 benzylamine hydrochloride 

Downstream Products

• 104669-74-1 benzyl carbamic acid allyl ester 
• 25855-24-7 N-benzyl-N'-cyclohexylurea 
• 1467-21-6 N-phenyl-N'-benzylurea 
• 335459-64-8 1-benzyl-3-(cyclohexylmethyl)urea 
• 3173-56-6 benzyl isothiocyanate 
• 57965-06-7 ethyl 2-(benzylcarbamoyl)hydrazine-1-carboxylate 
• 16312-86-0 4-benzyl-1,2,4-triazolidine-3,5-dione 
• 100-02-7 4-nitro-phenol 
• 39531-35-6 N-benzyl-N',N'-(1,5-pentamethylenediyl)urea 

Relevant articles and documents

Discovery of Biased Mu-Opioid Receptor Agonists for the Treatment of Pain

G protein-biased mu-opioid receptor (MOR) agonists have been developed as promising new potent analgesic drugs with fewer adverse side effects than standard MOR agonists. PZM21 represents a unique chemotype unrelated to known opioids, which makes it a desirable lead for modification to find analgesics with new chemical entities. In the present study, we synthesized and tested novel PZM21 derivatives as potent biased MOR agonists by introducing a benzodioxolane group to replace the hydroxybenzene of PZM21. The new compounds displayed more potent analgesic activities in vivo and greater bias toward G protein signaling in vitro than did PZM21. These results suggest that the benzodioxolane group is essential for the maintenance of bias. Compounds 7 i ((S)-1-(3-(benzo[d][1,3]dioxol-4-yl)-2-(dimethylamino)propyl)-3-phenethylurea) and 7 j ((S)-1-(3-(benzo[d][1,3]dioxol-4-yl)-2-(dimethylamino)propyl)-3-benzylurea) could serve as new leads for further modifications to find novel biased MOR agonists with greater G protein signaling potency and less β-arrestin-2 recruitment.

Synthesis and Biological Evaluation of 10-Substituted Camptothecin Derivatives with Improved Water Solubility and Activity

Despite remarkable clinical achievements, camptothecin (CPT) still suffers from poor solubility and severe toxicity. Therefore, it is necessary to redevelop CPT derivatives as supplementary antitumor agents with good water solubility and small side effects. In this work, 27 camptothecin derivatives were synthesized and screened for their cytotoxicity against A549 (lung) and HCT-116 (colon) cancer cell lines. Among them, compound B7, 7-ethyl-10-(2-oxo-2-(4-methylpiperidin-1-yl)ethoxy)camptothecin,was demonstrated in vitro to be a more potent antitumor agent than SN-38 by comparison of their inhibitory activities against cell proliferation and colony formation and interference effect on process of cell cycle and cell apoptosis. Additionally, a molecular docking model revealed that B7 can interact with the topoisomerase I–DNA complex, and that the solubility of B7 reached 5.73 μg/mL in water. Moreover, B7 significantly inhibited tumor growth in an A549 xenograft model at dosages of 0.4 and 2.0 mg/kg, and exhibited minimum lethal doses comparable to those of irinotecan. These results indicated that B7, with improved solubility, enhanced activity and acceptable acute toxicity, can be used as a lead compound for the development of novel anticancer agents.

A simple and efficient biphasic method for the preparation of 4-nitrophenyl N-methyl- and N-alkylcarbamates

Treatment of 4-nitrophenyl chloroformate with alkylammonium hydrochloride salts and solid anhydrous Na2CO3 in either CH2Cl2 or CH3CN gave 4-nitrophenyl N-methylcarbamate and other N-alkylcarbamate ana

The enhancement of enantioselectivities for lipase-catalyzed reactions by using carbamates

The enantioselectivity of porcine pancreatic lipase-catalyzed resolution of 1-indanol was enhanced up to 3 fold in the presence of carbamates. The optimum incubation time for 4-nitrophenyl-N-hexyl carbamate and the enzyme was 18 h before this biocatalytic resolution. The optimum concentration of the inhibitor 4-nitrophenyl-N-hexyl carbamate in this resolution was 1% mole equivalent of the substrate 1-indanol.

Biased agonist and medical application thereof

The invention relates to compounds shown in structural formulas I and II, stereoisomers or pharmaceutically acceptable salts thereof, and a pharmaceutical composition containing the compounds, the stereoisomers or the pharmaceutically acceptable salts thereof as active ingredients, and uses of the compound, the stereoisomer thereof or the pharmaceutically acceptable salt thereof in preparation ofanalgesic drugs.

Synthesis of Cyclic N-Hydroxylated Ureas and Oxazolidinone Oximes Enabled by Chemoselective Iodine(III)-Mediated Radical or Cationic Cyclizations of Unsaturated N-Alkoxyureas

In this study we describe the reactivity of unsaturated N-alkoxyureas in the presence of different combinations of a hypervalent iodine(III) reagent and a bromide source or TEMPO. Three complementary cyclizations can be achieved depending on the reaction conditions. On the one hand, PIFA with pyridinium bromide leads to an oxybromination reaction. On the other hand, bis(tert-butylcarbonyloxy)iodobenzene with tetrabutylammonium bromide or TEMPO triggers aminobromination or aminooxyamination reactions, respectively. Control experiments showed that the three reactions proceed through distinct mechanisms: the first process is ionic while the other two follow a radical manifold. (Figure presented.).

Reactive Oxygen Species-Triggered Tunable Hydrogen Sulfide Release

A series of carbamothioates with tunable release of H2S after activation by reactive oxygen species are reported. The half-lives of H2S release could be tuned from 24 to 203 min by varying the basicity of the amine.

METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY

Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5- diones from anilines

A simple and efficient three-step synthetic procedure for the preparation of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles), starting from anilines, has been developed. In this method, aniline derivatives were reacted with 4-nitrophenyl chloroformate to provide corresponding carbamate derivatives. In the second step, semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazate. The cyclization reaction of corresponding semicarbazides furnished 1,2,4-triazolidindiones in high yields. Copyright Taylor & Francis Group, LLC.

A novel naphthylmethyleneimino-type photocleavable protecting group for primary amines

A novel naphthylmethyleneimino-type protecting group for aliphatic and aromatic primary amines including α-amino acids was devised and its introduction was accomplished in good to excellent yields. This type of protecting group was found to be cleanly removed photochemically to regenerate the primary amines in good to high yields, regardless of steric and electronic properties. Georg Thieme Verlag Stuttgart.