6668-56-0

Usage

Uses

Used in Pharmaceutical Industry:
4-FLUORO-3-NITROBENZENESULFONYL CHLORIDE is used as a key intermediate in the synthesis of potent Bcl-2/Bcl-xL inhibitors. These inhibitors are crucial in the development of anti-cancer drugs due to their ability to target and disrupt the function of Bcl-2 and Bcl-xL proteins, which are known to promote cell survival and contribute to tumor growth. The use of 4-FLUORO-3-NITROBENZENESULFONYL CHLORIDE in the preparation of these inhibitors is driven by its reactivity and the potential for strong in vivo antitumor activity.

InChI:InChI=1/C6H3ClFNO4S/c7-14(12,13)4-1-2-5(8)6(3-4)9(10)11/h1-3H

Upstream product

• 1493-27-2 ortho-nitrofluorobenzene 
• 3888-84-4 4-fluoro-3-nitro-benzenesulfonic acid 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 

Downstream Products

• 306964-88-5 ethyl 1-[(3,4-diamino-phenyl)sulfonyl]-1H-pyrrole-2-carboxylate 
• 306964-87-4 ethyl 1-[(4-amino-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylate 
• 870812-28-5 4-(4-(2-fluorobenzyl)-4-methoxy-1-piperidinyl)-N'-((4-fluoro-3-nitrophenyl)sulfonyl)benzenecarboximidamide 
• 1069135-17-6 C₆H₃FN₄O₄S 
• 1338346-29-4 N-[2-(methyloxy)ethyl]-4-(4-morpholinylsulfonyl)-2-nitroaniline 
• 1376191-26-2 (R)-4-{[4-(dimethylamino)-1-(phenylthio)but-2-yl]amino}-N-(4-ethynylphenyl)-3-nitrobenzenesulfonamide 
• 1376190-41-8 (R)-N-(4-{4-[(4'-chloro-[1,1'-biphenyl]-2-yl)methyl]piperazin-1-yl}phenyl)-4-{[4-(dimethylamino)-1-(phenylthio)but-2-yl]amino}-3-nitrobenzenesulfonamide 
• 1376190-51-0 (R)-4-{[4-(dimethylamino)-1-(phenylthio)but-2-yl]amino}-3-nitro-N-[4-(piperazin-1-yl)phenyl]benzenesulfonamide 
• 1379604-76-8 4-(4-chlorophenyl)-1-[(S)-3,4-dihydroxybutyl]-3-(3-{4-[4-(4-{[(R)-4-(dimethylamino)-1-(phenylthio)but-2-yl]amino}-3-nitrophenylsulfonamido)phenyl]piperazin-1-yl}phenyl)-N-[3-(4-methylpiperazin-1-yl)propyl]-1H-pyrrole-2-carboxamide 
• 1379604-77-9 4-(4-chlorophenyl)-1-[(S)-3,4-dihydroxybutyl]-3-(3-{4-[4-(4-{[(R)-4-(dimethylamino)-1-(phenylthio)but-2-yl]amino}-3-nitrophenylsulfonamido)phenyl]-1H-1,2,3-triazol-1-yl}phenyl)-N-[3-(4-methylpiperazin-1-yl)propyl]-1H-pyrrole-2-carboxamide 
• 1376190-46-3 (R)-4-{[4-(dimethylamino)-1-(phenylthio)but-2-yl]amino}-3-nitro-N-phenylbenzenesulfonamide 
• 1376191-17-1 4-fluoro-3-nitro-N-phenylbenzenesulfonamide 
• 1376191-12-6 t-butyl 4-[4-(4-fluoro-3-nitrophenylsulfonamido)phenyl]piperazine-1-carboxylate 
• 1154161-03-1 3-amino-4-(morpholino)-N-methylbenzenesulfonamide 

Relevant academic research and scientific papers

New insights into 4-anilinoquinazolines as inhibitors of cardiac troponin I-interacting kinase (TNNI3K)

We report the synthesis of several related 4-anilinoquinazolines as inhibitors of cardiac troponin I-interacting kinase (TNNi3K). These close structural analogs of 3-((6,7-dimethoxyquinazolin-4-yl)amino)-4-(dimethylamino)-N-methylbenzenesulfonamide (GSK11

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.

Dihydropteridinone-sulfamide derivatives, pharmaceutically-acceptable salts of derivatives, preparation method of derivatives and application of derivatives and salts

The invention provides dihydropteridinone-sulfamide derivatives as well as a preparation method and application thereof aiming at problems in the prior art, and provides a novel choice for developmentof an antitumor drug for inhibiting a bromodomain (BRD4

BCL-2/BCL-XL INHIBITORS FOR USE IN THE TREATMENT OF CANCER

Inhibitors of Bcl-2/Bcl-xL and compositions containing the same are disclosed. Methods of using the Bcl-2/Bcl-xL inhibitors in the treatment of diseases and conditions wherein inhibition of Bcl-2/Bcl-xL provides a benefit, like cancers, also are disclosed

INHIBITOR OF INDOLEAMINE-2,3-DIOXYGENASE (IDO)

The present disclosure provides compounds of Formula (I). The compounds described herein may be useful in treating a disease associated with IDO, for example, cancer or an infectious disease (e.g., viral or bacterial infectious diseases). Also, provided in the present disclosure are pharmaceutical compositions, kits, methods, and uses including or using a compound described herein.

BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS

The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not

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.

Identification of Purines and 7-Deazapurines as Potent and Selective Type i Inhibitors of Troponin I-Interacting Kinase (TNNI3K)

A series of cardiac troponin I-interacting kinase (TNNI3K) inhibitors arising from 3-((9H-purin-6-yl)amino)-N-methyl-benzenesulfonamide (1) is disclosed along with fundamental structure-function relationships that delineate the role of each element of 1 for TNNI3K recognition. An X-ray structure of 1 bound to TNNI3K confirmed its Type I binding mode and is used to rationalize the structure-activity relationship and employed to design potent, selective, and orally bioavailable TNNI3K inhibitors. Identification of the 7-deazapurine heterocycle as a superior template (vs purine) and its elaboration by introduction of C4-benzenesulfonamide and C7- and C8-7-deazapurine substituents produced compounds with substantial improvements in potency (>1000-fold), general kinase selectivity (10-fold improvement), and pharmacokinetic properties (>10-fold increase in poDNAUC). Optimal members of the series have properties suitable for use in in vitro and in vivo experiments aimed at elucidating the role of TNNI3K in cardiac biology and serve as leads for developing novel heart failure medicines.

THERAPEUTIC COMPOUNDS AND COMPOSITIONS

Provided are aryl sulfonamide diarylurea derivative compounds that are inhibitors of mutant isocitrate dehydrogenase 1/2 (IDH 1/2), useful for treating cancer. Also provided are methods of treating cancer comprising administering to a subject in need thereof a compound described herein. Cancers that are treatable by the compounds of the invention are glioblastoma, myelodysplastic syndrome, myeloproliferative neoplasm, acute myelogenous leukemia, sarcoma, melanoma, non-small cell lung cancer, chondrosarcoma, and non-Hodgkin's lymphoma (NHL).

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.