256373-91-8

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-(CHLOROSULFONYL)-3-FUROATE is used as an intermediate in the synthesis of pharmaceuticals for its ability to facilitate the formation of various drug molecules.
Used in Agrochemical Industry:
ETHYL 5-(CHLOROSULFONYL)-3-FUROATE is used as an intermediate in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Dye and Pigment Production:
ETHYL 5-(CHLOROSULFONYL)-3-FUROATE is used in the production of dyes and pigments, playing a role in creating a wide range of colors for various applications.
Used in Organic Synthesis:
ETHYL 5-(CHLOROSULFONYL)-3-FUROATE is used as a reagent in organic synthesis, taking advantage of its strong chlorosulfonylating properties to aid in the creation of diverse organic compounds.
It should be noted that due to its potentially hazardous nature, ETHYL 5-(CHLOROSULFONYL)-3-FUROATE should be handled with care.

Upstream product

• 614-98-2 ethyl 3-furancarboxylate 
• 256373-92-9 ethyl 4-furoate-2-sulfonic acid 

Downstream Products

• 256373-94-1 ethyl 5-sulfamoylfuran-3-carboxylate 

Relevant academic research and scientific papers

Synthesis of deuterium-labelled analogues of NLRP3 inflammasome inhibitor MCC950

This study describes the syntheses of di, tetra and hexa deuterated analogues of the NOD-like receptor pyrin domain-containing protein 3 (NLRP3) inflammasome inhibitor MCC950. In di and tetra deuterated analogues, deuteriums were incorporated into the 1,2,3,5,6,7-hexahydro-s-indacene moiety, whereas in the hexa deuterated MCC950 deuteriums were incorporated into the 2-(furan-3-yl)propan-2-ol moiety. The di deuterated MCC950 analogue was synthesised from 4-amino-3,5,6,7-tetrahydro-s-indacen-1(2H)-one 5. Tetra deuterated analogues were synthesised in 10 chemical steps starting with 5-bromo-2,3-dihydro-1H-inden-1-one 9, whereas the hexa deuterated analogue was synthesised in four chemical steps starting with ethyl-3-furoate 24. All of the compounds exhibited similar activity to MCC950 (IC50 = 8 nM). These deuterated analogues are useful as internal standards in LC-MS analyses of biological samples from in vivo studies.

Discovery of a series of ester-substituted NLRP3 inflammasome inhibitors

The NLRP3 inflammasome is a component of the innate immune system involved in the production of proinflammatory cytokines. Aberrant activation by a wide range of exogenous and endogenous signals can lead to chronic, low-grade inflammation. It has attracted a great deal of interest as a drug target due to the association with diseases of large unmet medical need such as Alzheimer's disease, Parkinson's disease, arthritis, and cancer. To date, no drugs specifically targeting inhibition of the NLRP3 inflammasome have been approved. In this work, we used the known NLRP3 inflammasome inhibitor CP-456,773 (aka CRID3 or MCC 950) as our starting point and undertook a Structure-Activity Relationship (SAR) analysis and subsequent scaffold-hopping exercise. This resulted in the rational design of a series of novel ester-substituted urea compounds that are highly potent and selective NLRP3 inflammasome inhibitors, as exemplified by compounds 44 and 45. It is hypothesized that the ester moiety acts as a highly permeable delivery vehicle and is subsequently hydrolyzed to the carboxylic acid active species by carboxylesterase enzymes. These molecules are greatly differentiated from the state-of-the-art and offer potential in the treatment of NLRP3-driven diseases, particularly where tissue penetration is required.

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY

In one aspect, compounds of Formula A, or a pharmaceutically acceptable salt thereof, are featured (Formula A) or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein.

SULPHONAMIDES AND COMPOSITIONS THEREOF FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY

In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured: wherein the variables shown in Formula AA can be as defined anywhere herein. Compounds AA are modulators of NLRP1 and/or NLRP3

Sulfonamide compound and medical applications thereof

The invention discloses a compound containing a sulfonamide structure, a preparation method thereof, and medical applications of the compound, and more specifically discloses the compound with a structure represented by formula I, and a pharmaceutically acceptable salt or a prodrug or a solvate thereof. The compound is used for tumor treatment through inhibiting ATP-citrate lyase.

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY

In one aspect, compounds of Formulae (I) and (II), or pharmaceutically acceptable salts thereof, are featured; Formula (I), Formula (II) or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formulae (I) and (II) can be as defined anywhere herein.

Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors

Endothelial lipase (EL) activity has been implicated in HDL catabolism, vascular inflammation, and atherogenesis, and inhibitors are therefore expected to be useful for the treatment of cardiovascular disease. Sulfonylfuran urea 1 was identified in a high-throughput screening campaign as a potent and non-selective EL inhibitor. A lead optimization effort was undertaken to improve potency and selectivity, and modifications leading to improved LPL selectivity were identified. Radiolabeling studies were undertaken to establish the mechanism of action for these inhibitors, which were ultimately demonstrated to be irreversible inhibitors.

Novel synthesis of 1-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-[4-(1-hydroxy-1-methyl-ethyl) furan-2-sulfonyl]urea, An anti-inflammatory agent

A novel synthesis of the anti-inflammatory agent 1-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-[4-(1-hydroxy-1-methyl-ethyl)- furan-2-sulfonyl]urea 1 is described. Sulfonamide 5 was prepared starting from ethyl 3-furoate 2. Key steps were a one-pot sulfonylation with chlorosulfonic acid in methylene chloride followed by pyridinium salt formation and reaction with phosphorus pentachloride to provide ethyl 2-(chlorosulfonyl)-4-furoate 7. This sulfonyl chloride was treated with ammonium bicarbonate to form sulfonamide 8, followed by treatment with excess methyl magnesium chloride to provide 4-(1-hydroxy-1-methyl-ethyl)-furan-2-sulfonamide 5. 4-Isocyanato-1,2,3,5,6,7-hexahydro-s-indacene 16 was prepared from indan in five steps. The formation of the desired sulfonyl urea was carried out both with the isolated isocyanate 16 and via an in situ method.

A synthesis of furan sulfonamide compounds useful in the synthesis of IL-1 inhibitors

An efficent synthesis of furan sulfonamide compounds of formula ???comprising reacting a compound of formula II with a Grignard reagent in a reaction inert solvent, wherein R' is (C1-C6)alkyl. The compound of formula II is prepared by reacting a compound of formula III with a compound of formula IV wherein R' is (C1-C6)alkyl with a chorinating reagent and an acid scaverger in an inert solvent. The invention also includes a novel compound of the formula ???wherein R' is (C1-C6)alkyl and Q is halo, hydroxy or amino.

Efficient synthesis of furan sulfonamide compounds useful in the synthesis of new IL-1 inhibitors

An efficent synthesis of furan sulfonamide compounds of formula comprising reacting a compound of formula 11 with a Grignard reagent in a reaction inert solvent, wherein R' is (C1-C6)alkyl. The compound of formula II is prepared by reacting a compound of formula III with a compound of formula IV wherein R' is (C1-C6)alkyl with a chorinating reagent and an acid scaverger in an inert solvent. The invention also includes a novel compound of the formula wherein R' is (C1-C6)alkyl and Q is halo, hydroxy or amino.