7159-96-8

Usage

Uses

Used in Chemical Synthesis:
ETHYL (3-HYDROXYPHENYL)CARBAMATE is used as an intermediate in the synthesis of Phenmedipham-ethyl (P314605), which is an impurity of Phenmedipham (P314600). This application is crucial for the production of specific chemicals and compounds.
Used in Agriculture:
In the agricultural industry, ETHYL (3-HYDROXYPHENYL)CARBAMATE is used as a component in the production of Phenmedipham, a carbanilate selective herbicide. This herbicide is applied post-emergence in beet crops, targeting the control of most broad-leaved weeds before they develop. The use of ETHYL (3-HYDROXYPHENYL)CARBAMATE in this context helps improve the effectiveness of weed control strategies in agriculture.

InChI:InChI=1/C9H11NO3/c1-2-13-9(12)10-7-4-3-5-8(11)6-7/h3-6,11H,2H2,1H3,(H,10,12)

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 591-27-5 m-Hydroxyaniline 

Downstream Products

• 58632-48-7 (4-methyl-2-oxo-2H-1-benzopyran-7-yl)carbamic acid ethyl ester 
• 63450-46-4 7-(Carbethoxyamido)-4-(trifluoromethylcoumarin) 
• 85157-20-6 ethyl 7-N-(carbethoxy)aminocoumarin-4-acetate 
• 83263-90-5 (3-Oxiranylmethoxy-phenyl)-carbamic acid ethyl ester 
• 141692-64-0 methyl 7-ethoxycarbonylaminocoumarin-4-acetate 
• 113578-09-9 N-(2'-Ethoxycarbonylamino-4'-hydroxy-azobenzol-4-carbonyl)-L-glutaminsaeure 
• 6266-19-9 (4-ethoxycarbonylamino-2-hydroxy-phenyl)-arsonic acid 
• 147963-30-2 [4-(chloromethyl)-2-oxo-2H-1-benzopyran-7-yl]-carbamic acid ethyl ester 
• 147963-22-2 7-amino-4-(chloromethyl)-2H-1-benzopyran-2-one 
• 85157-21-7 2-(7-amino-2-oxo-2H-chromen-4-yl)acetic acid 
• 113578-10-2 N-<4-(3,6-Dioxo-2,3,4,6-tetrahydro-1,2,4-benzotriazin-2-yl)benzoyl>-L-glutaminsaeure 
• 113578-11-3 N-<4-(3,6-Dioxo-2,3,4,6-tetrahydro-1,2,4-benzotriazin-2-yl)benzoyl>-L-glutaminsaeure Diammoniumsalz 
• 26093-31-2 7-amino-4-methylcoumarin. 
• 75957-52-7 7-(N^α-benzyloxycarbonyl-α-benzyl-γ-L-glutaminyl)-4-methylcoumarinylamide 

Relevant academic research and scientific papers

Atom arrangement strategy for designing a turn-on 1H magnetic resonance probe: A dual activatable probe for multimodal detection of hypochlorite

The first dual activatable hypochlorite (-OCl)-sensing probe was developed, based on a new proof-of-concept design involving signal-activatable 1H chemical probes using the triple-resonance NMR technique. The probe enabled fluorescen

Marine natural products as inhibitors of cystathionine beta-synthase activity

A library consisting of characterized marine natural products as well as synthetic derivatives was screened for compounds capable of inhibiting the production of hydrogen sulfide (H2S) by cystathionine beta-synthase (CBS). Eight hits were valid

O-fluorination of aromatic azides yields improved azido-based fluorescent probes for hydrogen sulfide: Synthesis, spectra, and bioimaging

Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple biological functions. To visualize the endogenous in situ production of H2S in real time, new coumarin- and boron-dipyrromethene- based fluorescent turn-on probes were developed for fast sensing of H2S in aqueous buffer and in living cells. Introduction of a fluoro group in the ortho position of the aromatic azide can lead to a greater than twofold increase in the rate of reaction with H2S. On the basis of o-fluorinated aromatic azides, fluorescent probes with high sensitivity and selectivity toward H2S over other biologically relevant species were designed and synthesized. The probes can be used to in situ to visualize exogenous H2S and d-cysteine-dependent endogenously produced H2S in living cells, which makes them promising tools for potential applications in H2S biology.

Multicolor GLUT5-permeable fluorescent probes for fructose transport analysis

The specificity of carbohydrate transporters towards their substrates poses a significant challenge for the development of molecular probes to monitor sugar uptake in cells for biochemical and biomedical applications. Herein we report a new set of coumarin-based fluorescent sugar conjugates applicable for the analysis of fructose uptake due to their free passage through the fructose-specific transporter GLUT5. The reported probes cover a broad range of the fluorescence spectrum providing essential tools for the evaluation of fructose transport capacity in live cells.

A Suite of Activity-Based Probes to Dissect the KLK Activome in Drug-Resistant Prostate Cancer

Kallikrein-related peptidases (KLKs) are a family of secreted serine proteases, which form a network (the KLK activome) with an important role in proteolysis and signaling. In prostate cancer (PCa), increased KLK activity promotes tumor growth and metastasis through multiple biochemical pathways, and specific quantification and tracking of changes in the KLK activome could contribute to validation of KLKs as potential drug targets. Herein we report a technology platform based on novel activity-based probes (ABPs) and inhibitors enabling simultaneous orthogonal analysis of KLK2, KLK3, and KLK14 activity in hormone-responsive PCa cell lines and tumor homogenates. Importantly, we identifed a significant decoupling of KLK activity and abundance and suggest that KLK proteolysis should be considered as an additional parameter, along with the PSA blood test, for accurate PCa diagnosis and monitoring. Using selective inhibitors and multiplexed fluorescent activity-based protein profiling (ABPP), we dissect the KLK activome in PCa cells and show that increased KLK14 activity leads to a migratory phenotype. Furthermore, using biotinylated ABPs, we show that active KLK molecules are secreted into the bone microenvironment by PCa cells following stimulation by osteoblasts suggesting KLK-mediated signaling mechanisms could contribute to PCa metastasis to bone. Together our findings show that ABPP is a powerful approach to dissect dysregulation of the KLK activome as a promising and previously underappreciated therapeutic target in advanced PCa.

Targeting of glut5 for transporter-mediated drug-delivery is contingent upon substrate hydrophilicity

Specific link between high fructose uptake and cancer development and progression highlighted fructose transporters as potential means to achieve GLUT-mediated discrimination between normal and cancer cells. The gained expression of fructose-specific transporter GLUT5 in various cancers offers a possibility for developing cancer-specific imaging and bioactive agents. Herein, we explore the feasibility of delivering a bioactive agent through cancer-relevant fructose-specific transporter GLUT5. We employed specific targeting of GLUT5 by 2,5-anhydro-D-mannitol and investigated several drug conjugates for their ability to induce cancer-specific cytotoxicity. The proof-of-concept analysis was carried out for conjugates of chlorambucil (CLB) in GLUT5-positive breast cancer cells and normal breast cells. The cytotoxicity of conjugates was assessed over 24 h and 48 h, and significant dependence between cancer-selectivity and conjugate size was observed. The differences were found to relate to the loss of GLUT5-mediated uptake upon increased conjugate size and hydrophobicity. The findings provide information on the substrate tolerance of GLUT5 and highlight the importance of maintaining appropriate hydrophilicity for GLUT-mediated delivery.

Novel coumarin-based pH sensitive fluorescent probes for the highly alkaline pH region

The design, synthesis and spectroscopic properties of novel polymerizable coumarin-based pH indicators are reported. They show a fluorescence response to pH in the highly alkaline pH region with calculated pKa values in the range of 12.2–12.5. Covalent immobilization of the indicators to polymer supports provides novel pH-sensitive materials that possess excellent photostability. The materials are sensitive to pH in a similar range and can be applied in optical pH sensors for measuring pH in various alkaline media.

Coumarin Schiff base derivative as well as preparation method and application thereof

The invention relates to a coumarin Schiff base derivative as well as a preparation method and application thereof, belonging to the technical field of metal ion detection. The coumarin Schiff base compound is 2-hydroxyl Schiff base-4-methylcoumarin. The specific structural formula of the coumarin Schiff base derivative is as shown in the specification. The invention further relates to a preparation method and application of the coumarin Schiff base derivative. The coumarin Schiff base derivative is high in Cr selectivity and Cr sensitivity, high in binding capacity and beneficial forCr detection.

Gasotransmitter Regulation of Phosphatase Activity in Live Cells Studied by Three-Channel Imaging Correlation

Enzyme activity in live cells is dynamically regulated by small-molecule transmitters for maintaining normal physiological functions. A few probes have been devised to measure intracellular enzyme activities by fluorescent imaging, but the study of the re

Evaluation of novel coumarin-proline sulfonamide hybrids as anticancer and antidiabetic agents

Cancer and diabetes are considered as two major diseases affecting human health worldwide. Various therapies are available for treatment of cancer and diabetes individually, peptide linkage containing proline sulfonamide can be a promising therapy for treatment of both cancer as well as diabetes. Here, we report design and synthesis of novel coumarin-proline sulfonamide derivatives as anticancer and antidiabetic agents. All the synthesized compounds were screened for their anticancer activity against lungs cancer cell line (A549) and breast cancer cell line (MCF7) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide dye (MTT)assay and antidiabetic activity using DPP-IV inhibition assay. Compound 16b showed excellent activity against breast cancer cell line (MCF7) with IC50 value of 1.07 μM. All compounds showed moderate DPP-IV inhibition.