Category: 2740-88-7

Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor was written by Spencer, Emma S.;Dale, Edward J.;Gommans, Aimee L.;Rutledge, Malcolm T.;Vo, Christine T.;Nakatani, Yoshio;Gamble, Allan B.;Smith, Robin A. J.;Wilbanks, Sigurd M.;Hampton, Mark B.;Tyndall, Joel D. A.. And the article was included in European Journal of Medicinal Chemistry in 2015.Formula: C8H6FNS This article mentions the following:

Macrophage migration inhibitory factor (MIF) is a pleiotropic cytokine that has roles in the innate immune response, and also contributes to inflammatory disease. While the biol. properties of MIF are closely linked to protein-protein interactions, MIF also has tautomerase activity. Inhibition of this activity interferes with the interaction of MIF with protein partners e.g. the CD74 receptor, and tautomerase inhibitors show promise in disease models including multiple sclerosis and colitis. Isothiocyanates inhibit MIF tautomerase activity via covalent modification of the N-terminal proline. We systematically explored variants of benzyl and phenethyl isothiocyanates, to define determinants of inhibition. In particular, substitution with hydroxyl, chloro, fluoro and trifluoro moieties at the para and meta positions were evaluated. In assays on treated cells and recombinant protein, the IC₅₀ varied from 250 nM to >100 娓璏. X-ray crystal structures of selected complexes revealed that two binding modes are accessed by some compounds, perhaps owing to strain in short linkers between the isothiocyanate and aromatic ring. The variety of binding modes confirms the existence of two subsites for inhibitors and establishes a platform for the development of potent inhibitors of MIF that only need to target one of these subsites. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Formula: C8H6FNS).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters contain a carbonyl center, which gives rise to 120鎺?C閳ユ弲閳ユ彊 and O閳ユ弲閳ユ彊 angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C閳ユ彊閳ユ弲 bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Formula: C8H6FNS

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A Nanomolar-Potency Small Molecule Inhibitor of Regulator of G-Protein Signaling Proteins was written by Blazer, Levi L.;Zhang, Haoming;Casey, Emma M.;Husbands, Stephen M.;Neubig, Richard R.. And the article was included in Biochemistry in 2011.Electric Literature of C8H6FNS This article mentions the following:

Regulators of G-protein signaling (RGS) proteins are potent neg. modulators of signal transduction through G-protein-coupled receptors. They function by binding to activated (GTP-bound) Gα subunits and accelerating the rate of GTP hydrolysis. Modulation of RGS activity by small mols. is an attractive mechanism for fine-tuning GPCR signaling for therapeutic and research purposes. Here we describe the pharmacol. properties and mechanism of action of CCG-50014, the most potent small mol. RGS inhibitor to date. It has an IC₅₀ for RGS4 of 30 nM and is >20-fold selective for RGS4 over other RGS proteins. CCG-50014 binds covalently to the RGS, forming an adduct on two cysteine residues located in an allosteric regulatory site. It is not a general cysteine alkylator as it does not inhibit activity of the cysteine protease papain at concentrations >3000-fold higher than those required to inhibit RGS4 function. It is also >1000-fold more potent as an RGS4 inhibitor than are the cysteine alkylators N-ethylmaleimide and iodoacetamide. Anal. of the cysteine reactivity of the compound shows that compound binding to Cys¹⁰⁷ in RGS8 inhibits Gα binding in a manner that can be reversed by cleavage of the compound-RGS disulfide bond. If the compound reacts with Cys¹⁶⁰ in RGS8, the adduct induces RGS denaturation, and activity cannot be restored by removal of the compound The high potency and good selectivity of CCG-50014 make it a useful tool for studying the functional roles of RGS4. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Electric Literature of C8H6FNS).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Electric Literature of C8H6FNS

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Convenient synthesis of 5-arylidene-2-imino-4-thiazolidinone derivatives using microwave irradiation was written by Sarkis, Manal;Tran, Diem-Ngan;Dasso Lang, Maria Chiara;Garbay, Christiane;Braud, Emmanuelle. And the article was included in Synlett in 2014.Quality Control of 4-Fluorobenzylisothiocyanate This article mentions the following:

A concise approach for the preparation of 5-arylidene-2-imino-4-thiazolidinone derivatives, e.g., I, is described. Structurally diverse amines, isothiocyanates, aldehydes, and chloroacetyl chloride were combined under microwave irradiation to afford new 5-arylidene-2-imino-4-thiazolidinone derivatives The one-pot synthesis involves the in situ formation of a thiourea followed by reaction with chloroacetyl chloride and an aldehyde to generate the target compounds In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Quality Control of 4-Fluorobenzylisothiocyanate).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Quality Control of 4-Fluorobenzylisothiocyanate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Intermolecular alkyl/aryl exchange of 2-iminothiazoles with isothiocyanates and isocyanates: scopes and limitations was written by Shin, Dongyun;Lee, Jihoon;Hahn, Hoh-Gyu. And the article was included in Tetrahedron in 2010.Product Details of 2740-88-7 This article mentions the following:

2-Iminothiazole, an isoform of 2-aminothiazole, is a scaffold of synthetic and medicinal significance. An efficient method by which alkyl group attached to the imine nitrogen of 2-alkyliminothiazoles is changed into other alkyl groups by isothiocyanates is reported. All the reactions were carried out in toluene at 105° without any additive. The reaction is a reversible process and the equilibrium is determined by the reactivity of both reactants, in which the more electron-withdrawing alkyl or aryl groups at the 2-imino group or isothiocyanate showed higher reactivities. A synthetic problem in 2-iminothiazole chem., synthesis of amino acid-derived 2-iminothiazole was solved in a very simple manner. Using suitably designed 2-iminothiazole substrate, the electrophilic reactivity of various isothiocyanates could be empirically compared by this exchange reaction. Moreover, successful exchange reaction using isocyanates instead of isothiocyanates broadened the utility of this reaction. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Product Details of 2740-88-7).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Product Details of 2740-88-7

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics