406233-31-6

Basic information

• Product Name: 4-Fluoro-3-nitrobenzenesulfonamide
• Synonyms: 4-FLUORO-3-NITRO-BENZENESULFONAMIDE;4-fluoro-3-nitrobenzene-1-sulfonaMide;BenzenesulfonaMide, 4-fluoro-3-nitro-;4-Fluoro-3-nitrobenzensulfonaMide;2-Bromo-6-(2-methyl-1,3-dioxolane-2-yl)-pyridine
• CAS NO: 406233-31-6
• Molecular Formula: C₆H₅FN₂O₄S
• Molecular Weight: 220.1783032
• Product Categories: Aromatics;Intermediates;Sulfur & Selenium Compounds
• Mol File: 406233-31-6.mol

Chemical Properties

• Melting Point: 137.0 to 141.0 °C
• Boiling Point: 411.103°C at 760 mmHg
• Flash Point: 202.428°C
• Appearance: /
• Density: 1.637
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dimethylformamide, DMSO, Methanol
• PKA: 9.39±0.60(Predicted)
• CAS DataBase Reference: 4-Fluoro-3-nitrobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-3-nitrobenzenesulfonamide(406233-31-6)
• EPA Substance Registry System: 4-Fluoro-3-nitrobenzenesulfonamide(406233-31-6)

Safety Data

• Hazardous Substances Data: 406233-31-6(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
4-Fluoro-3-nitrobenzenesulfonamide is used as a reagent for the synthesis of substituted arylsulfonamide derivatives. Its unique chemical structure allows it to serve as a key intermediate in the production of various organic compounds with potential applications in different industries.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Fluoro-3-nitrobenzenesulfonamide is used as a building block for the development of new drugs. Its chemical properties make it a valuable component in the synthesis of novel medicinal compounds, particularly those targeting specific biological pathways or receptors.
3. Used in Research and Development:
4-Fluoro-3-nitrobenzenesulfonamide is also utilized in research and development settings, where it can be employed to study the effects of structural modifications on the properties and reactivity of arylsulfonamide derivatives. This knowledge can be applied to design and develop new molecules with improved or specific functionalities.
4. Used in Material Science:
In the field of material science, 4-Fluoro-3-nitrobenzenesulfonamide may find applications in the development of advanced materials with tailored properties. Its incorporation into polymers or other materials can potentially enhance their performance characteristics, such as stability, reactivity, or selectivity.

InChI:InChI=1/C6H5FN2O4S/c7-5-2-1-4(14(8,12)13)3-6(5)9(10)11/h1-3H,(H2,8,12,13)

Upstream product

• 1336-21-6 ammonium hydroxide 
• 1493-27-2 ortho-nitrofluorobenzene 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 3888-84-4 4-fluoro-3-nitro-benzenesulfonic acid 
• 6668-56-0 4-fluoro-3-nitrobenzene-1-sulfonyl chloride 

Downstream Products

• 406234-40-0 4-(2-methyl-1-(phenylthio)propan-2-ylamino)-3-nitrobenzenesulfonamide 
• 1228779-96-1 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 
• 1228780-12-8 4-(3-morpholinopropylamino)-3-nitrobenzenesulfonamide 
• 1228875-84-0 4-(1-cyclopropylpiperidin-4-ylamino)-3-nitrobenzenesulfonamide 
• 1228838-56-9 4-((4-fluorotetrahydro-2H-pyran-4-yl)methoxy)-3-nitrobenzenesulfonamide 
• 1377582-41-6 4-isopropoxy-3-nitro-benzenesulfonamide 
• 1377963-20-6 tert-butyl 5-(2-((2-isopropoxy-5-sulfamoylphenyl)amino)thiazol-4-yl)-5',6'-dihydro-[2,4'-bipyridine]-1'(2'H)-carboxylate 
• 1377963-23-9 tert-butyl 4-(5-(2-((2-isopropoxy-5-sulfamoylphenyl)amino)thiazol-4-yl)pyridin-2-yl)piperidine-1-carboxylate 

Relevant articles and documents

Design, synthesis, and bioactivity evaluation of novel Bcl-2/HDAC dual-target inhibitors for the treatment of multiple myeloma

Multiple myeloma (MM) is the second most common haematological malignancy. Almost all patients with MM eventually relapse, and most recommended treatment protocols for the patients with relapsed refractory MM comprise a combination of drugs with different mechanisms of action. Therefore novel drugs are in urgent need in clinic. Bcl-2 inhibitors and HDAC inhibitors were proved their anti-MM effect in clinic or under clinical trials, and they were further discovered to have synergistic interactions. In this study, a series of Bcl-2/HDAC dual-target inhibitors were designed and synthesized. Among them, compounds 7e–7g showed good inhibitory activities against HDAC6 and high binding affinities to Bcl-2 protein simultaneously. They also displayed good growth inhibitory activities against human MM cell line RPMI-8226, which proved their potential value for the treatment of multiple myeloma.

iSPAAC: Isomer-Free Generation of a Bcl-xL-Inhibitor in Living Cells

Strain-promoted azide–alkyne cycloadditions (SPAAC) have proven extremely useful for labeling of biomolecules, but typically produce isomeric mixtures. This is not appropriate for the formation of bioactive molecules in living cells. Here, the first use o

INHIBITING B-CELL LYMPHOMA 2 (BCL-2) AND RELATED PROTEINS

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Amplified synthesis method of 3-nitro-4-halogeno-benzenesulfonamide

An amplified synthesis method of 3-nitro-4-halogeno-benzenesulfonamide is disclosed. According to the method, 4-halogeno-benzenesulfonyl chloride which is used as a raw material undergoes nitration to prepare 3-nitro-4-halogeno-benzenesulfonyl chloride; and after aminolysis, 3-nitro-4-halogeno-benzenesulfonamide is prepared. By the synthesis method provided by the invention, the synthesis route by the adoption of chlorosulfonic acid is changed, and production safety is remarkably raised. The reaction condition is milder and is easy for production control. Thus, mass production of the compound is easier to implement and realize.

Design, synthesis, and activity evaluation of selective inhibitors of anti-apoptotic Bcl-2 proteins: The effects on the selectivity of the P1 pockets in the active sites

The anti-apoptotic Bcl-2 proteins are attractive targets for anti-cancer drug development, and the discovery of their selective inhibitors has become a research focus. In this Letter, obvious differences in the P1 pocket of the active site between Bcl-2, Bcl-xL, and Mcl-1 proteins were proposed by the structural comparison of these proteins. As a result, the groups in their inhibitors binding to the P1 pockets may have significant effect on the selectivity for these proteins. Based on this hypothesis, five types of derivatives of the lead compound B-1 were designed, and several highly selective inhibitors of Bcl-xL(E-1) or Mcl-1 proteins (G) were found. The selective inhibitors of Mcl-1 protein found in this Letter provide new structural types for the development of novel antitumor agents.

CHEMICAL COMPOUNDS

The present invention relates to compounds of Formula (I): and to their salts, pharmaceutical compositions, methods of use, and methods for their preparation. These compounds inhibit Bcl-2 and/or Bcl-XL activities and may be used for the treatment of cancer.

Design, synthesis, and activity evaluation of broad-spectrum small-molecule inhibitors of anti-apoptotic Bcl-2 family proteins: Characteristics of broad-spectrum protein binding and its effects on anti-tumor activity

On the basis of the comparison of the structure of the Bim BH3: Bcl-x L complex and that of the ABT-737: Bcl-xL complex, a series of class A compounds were designed. These compounds had the basic skeleton of ABT-737 and the h2 residues of Bim BH3. These residues had shown themselves to be relevant to Bim BH3's broad-spectrum binding properties in saturation mutagenesis assays. Unlike ABT-737, which is a selective inhibitor of anti-apoptotic members of the Bcl-2 protein family, the class A compounds showed broad-spectrum binding activity to target proteins similar to those of Bim BH3 peptide. Then class B compounds were synthesized by modifying the structure of the most effective class A compound, A-4. Most of these class B compounds showed better binding affinity to the target proteins than the class A compounds had. They also showed themselves more effective than ABT-737 at inhibiting growth in multiple tumor cell lines known to express Bcl-x L, Bcl-2, and Mcl-1 proteins at high levels. Compounds B-11 and B-12 had the strongest anti-tumor activity of any compounds we produced. This study suggests that it is feasible to design small-molecule inhibitors based on the structure of Bim BH3, which shows broad-spectrum binding to Bcl-xL, Bcl-2, and Mcl-1 proteins. Our results also suggest that the broad-spectrum properties of small-molecule inhibitors binding to target proteins play a critical role in inhibiting the growth of many tumor cells. Finally, our study provides a series of lead compounds that merit further research into anti-cancer therapeutics.

BIS HETEROARYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables A, Q, J, R1, R3, and R5 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

FUSED HETEROARYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables A, Q, J, R1, R3, and R5 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

PYRIDYL-THIAZOLYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables Rz, Q, J, R1, R3, R5, and R6 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.