4650-60-6

Usage

Uses

Used in the Food Industry:
2-Furfuryl isothiocyanate is utilized as a flavoring agent to impart a pungent, spicy flavor to food products such as mustard, horseradish, and wasabi. Its strong, mustard-like aroma is particularly valued for enhancing the sensory experience of these foods.
Used in Pharmaceutical Research:
2-FURFURYL ISOTHIOCYANATE has been studied for its potential antimicrobial properties, suggesting that it could be used as an antimicrobial agent in pharmaceutical formulations to combat various infections.
Used in Antimicrobial Applications:
2-Furfuryl isothiocyanate is being investigated for its potential as an antimicrobial ingredient, which could be incorporated into products to prevent the growth of harmful microorganisms, thereby improving product safety and shelf life.

InChI:InChI=1/C6H5NOS/c9-5-7-4-6-2-1-3-8-6/h1-3H,4H2

Upstream product

• 1436862-81-5 o-phenyl (furan-2-ylmethyl)carbamothioate 
• 617-89-0 furan-2-ylmethanamine 
• 1005-56-7 phenylcarbonochloridothioate 
• 463-71-8 thiophosgene 
• 31596-38-0 C₆H₇NOS₂*C₆H₁₅N 
• 75-09-2 dichloromethane 
• 7732-18-5 water 
• 75-15-0 carbon disulfide 

Downstream Products

• 88352-24-3 2-S-Methyl-1-phenyl-5-(2-furfuryl)isodithiobiuret 
• 88352-33-4 2-S-Methyl-1-(3-chlorophenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-26-5 2-S-Methyl-1-(4-methylphenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-32-3 2-S-Methyl-1-(2-chlorophenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-34-5 2-S-Methyl-1-(4-chlorophenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-27-6 2-S-Methyl-1-(4-ethylphenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-35-6 2-S-Methyl-1-(3-bromophenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-31-2 2-S-Methyl-1-(3-methoxyphenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-30-1 2-S-Methyl-1-(4-chloro-2-methylphenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-29-8 2-S-Methyl-1-(2,4,6-trimethylphenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-28-7 2-S-Methyl-1-(4-isopropylphenyl)-5-(2-furfuryl)isodithiobiuret 
• 88352-36-7 2-S-Methyl-1-(3-trifluoromethylphenyl)-5-(2-furfuryl)isodithiobiuret 
• 56541-07-2 furfurylthiourea 
• 161370-06-5 N-(2-Furanylmethyl)-α-methyl-α-(phenylmethyl)-2-pyridineethanimidothioic acid, methyl ester 

Relevant academic research and scientific papers

4-Dimethylaminopyridine-catalyzed synthesis of isothiocyanates from amines and carbon disulfide

Isothiocyanates were synthesized by reactions between primary amines and CS2 in the presence of 4-dimethylaminopyridine as a catalyst and tert-butyl hydroperoxide as an oxidant. Various aryl, benzyl, alkyl, and hydroxyl amines were transformed into the corresponding isothiocyanates in 41–82% yields.

Synthesis and Evaluation of Novel Quinazolinone Derivatives as Potential Anti-HCC Agents

Hepatocellular carcinoma (HCC), a common malignancy worldwide, has a high mortality rate and limited effective therapeutic options. In this work, a series of quinazolinone compounds (6a–t and 7a–i) were synthesized as potential anti-HCC agents. Among them, compound 7b more potently inhibited HepG2, HUH7 and SK-Hep-1 cells proliferation than classical anti-HCC drug sorafenib, indicating its potential anti-HCC effect. Interestingly, 7b could dose-dependently decrease Cyclin D1 and CDK2 levels, and increase p21 protein expression, thus inducing HepG2 cells cycle arrest at G0/G1 phase. In addition, 7b also displayed potent apoptosis-induced effect on HepG2 cells by interfering Bad, Bax, Bcl-2 and Bcl-xl proteins expression. Notably, 7b could efficiently block the activity of PI3K pathway by dose-dependently reducing the phosphorylation of PI3K (Y607) and AKT (S473). Moreover, predicted ADME properties indicated that 7b possessed a good pharmacokinetic profile. Collectively, compound 7b might be a promising lead to the development of novel therapeutic agents towards HCC.

Discovery of novel quinazolinone derivatives as potential anti-HBV and anti-HCC agents

As a continuation of earlier works, a series of novel quinazolinone derivatives (5a-s) were synthesized and evaluated for their in vitro anti-HBV and anti-hepatocellular carcinoma cell (HCC) activities. Among them, compounds 5j and 5k exhibited most potent inhibitory effect on HBV DNA replication in both drug sensitive and resistant (lamivudine and entecavir) HBV strains. Interestingly, besides the anti-HBV effect, compound 5k could significantly inhibit the proliferation of HepG2, HUH7 and SK- cells, with IC50 values of 5.44, 6.42 and 6.75 μM, respectively, indicating its potential anti-HCC activity. Notably, the in vitro anti-HCC activity of 5k were more potent than that of positive control 5-fluorouracil and sorafenib. Further studies revealed that compound 5k could induce HepG2 cells apoptosis by dose-dependently upregulating Bad and Bax expression and decreasing Bcl-2 and Bcl-xl protein level. Considering the potent anti-HBV and anti-HCC effect, compound 5k might be a promising lead to develop novel therapeutic agents towards HBV infection and HBV-induced HCC.

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.

The synthesis of sulforaphane analogues and their protection effect against cisplatin induced cytotoxicity in kidney cells

A series of sulforaphane analogues were synthesized with various amines by treatment of carbon disulfide followed by Boc2O and DMAP. These synthesized sulforaphane analogues were tested on cisplatin treated cultured LLC-PK1 kidney cell line. Among these analogues, several compounds including SF5 show a potent effect on kidney cell protection assay at the concentration of 2.5 μM. Further studies with compound SF5 revealed that the kidney cell protection effect was related by inhibiting the apoptosis pathway through JNK-p53-caspase apoptotic cascade. Compound SF5 may be considered as a promising candidate for the development of new kidney protection agent against drug induced acute kidney disease.

Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process

A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.

ISOTHIOCYNATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIONS CONTAINING SAME

The present invention provides glucosinolate and isothiocyanate compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.

Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts

We have developed a general economical and environmentally benign method for the preparation of isothiocyanates from the corresponding dilhiocarbamic acid salts by using cheap and readily available reagent molecular iodine. This is perhaps the most efficient method reported so far for the synthesis of isothiocyanates. The reagent is easily available and nontoxic, and the precipitated sulfur can be removed easily; hence, this method is most suitable for large-scale synthesis. Wiley-VCH Verlag GmbH & Co. KGaA.

ISOTHIOCYANATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIOS CONTAINING SAME

The present invention provides glucosinolate and isothiocyante compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.