34634-22-5

Usage

Uses

Used in Chemical Research and Organic Synthesis:
2,2-Diphenylethyl isothiocyanate is used as a reagent for the introduction of isothiocyanate functional groups into organic molecules, facilitating the synthesis of various organic compounds.
Used in Pesticide Industry:
2,2-Diphenylethyl isothiocyanate is used as an insecticide and fungicide due to its strong odor and potential to control pests and fungi.
Used in Cancer Therapy:
2,2-Diphenylethyl isothiocyanate is used as an anticancer agent, showing potential in the treatment of various types of cancer. It has been studied for its ability to target and inhibit the growth of cancer cells.
Used in Anti-inflammatory and Analgesic Applications:
2,2-Diphenylethyl isothiocyanate has been investigated for its potential as an anti-inflammatory and analgesic agent, with the capacity to reduce inflammation and alleviate pain.

InChI:InChI=1/C15H13NS/c17-12-16-11-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10,15H,11H2

Upstream product

• 75-15-0 carbon disulfide 
• 3963-62-0 2,2-Diphenylethylamine 
• 463-71-8 thiophosgene 

Downstream Products

• 1234495-38-5 1,11-bis-{3-[1-(2,2-diphenylethyl)thioureado]}-4,8-[N-(tert-butyl)oxycarbonyl]-4,8-diazaundecane 
• 1234495-36-3 1,15-bis-{3-[1-(2,2-diphenylethyl)thioureado]}-4,12-[N-(tert-butyl)oxycarbonyl]-4,12-diazapentadecane 
• 1234495-37-4 1,12-bis-{3-[1-(2,2-diphenylethyl)thioureado]}-4,9-[N-(tert-butyl)oxycarbonyl]-4,9-diazadodecane 

Relevant academic research and scientific papers

Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R

Even today, the role of the histamine H2 receptor (H2R) in the central nervous system (CNS) is widely unknown. In previous research, many dimeric, high-affinity and subtype-selective carbamoylguanidine-type ligands such as UR-NK22 (5, pKi = 8.07) were reported as H2R agonists. However, their applicability to the study of the H2R in the CNS is compromised by their molecular and pharmacokinetic properties, such as high molecular weight and, consequently, a limited bioavailability. To address the need for more drug-like H2R agonists with high affinity, we synthesized a series of monomeric (thio)carbamoylguanidine-type ligands containing various spacers and side-chain moieties. This structural simplification resulted in potent (partial) agonists (guinea pig right atrium, [35S]GTPγS and β-arrestin2 recruitment assays) with human (h) H2R affinities in the one-digit nanomolar range (pKi (139, UR-KAT523): 8.35; pKi (157, UR-MB-69): 8.69). Most of the compounds presented here exhibited an excellent selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity at the hD3R (e.g. pKi (139, UR-KAT523): 7.80; pKi (157, UR-MB-69): 8.06). In summary, we developed a series of novel, more drug-like H2R and D3R agonists for the application in recombinant systems in which either the H2R or the D3R is solely expressed. Furthermore, our ligands are promising lead compounds in the development of selective H2R agonists for future in vivo studies or experiments utilizing primary tissue to unravel the role and function of the H2R in the CNS.

Direct, Microwave-Assisted Synthesis of Isothiocyanates

A microwave-assisted desulfuration of readily available dithiocarbamates, formed in situ from primary amines, leading to target isothiocyanates has been developed. This efficient protocol provides a rapid, environmentally benign route to aliphatic and aromatic isothiocyanates.

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.

HPLC-based kinetics assay facilitates analysis of systems with multiple reaction products and thermal enzyme denaturation

Glucosinolates are plant secondary metabolites abundant in Brassica vegetables that are substrates for the enzyme myrosinase, a thioglucoside hydrolase. Enzyme-mediated hydrolysis of glucosinolates forms several organic products, including isothiocyanates (ITCs) that have been explored for their beneficial effects in humans. Myrosinase has been shown to be tolerant of non-natural glucosinolates, such as 2,2-diphenylethyl glucosinolate, and can facilitate their conversion to non-natural ITCs, some of which are leads for drug development. An HPLC-based method capable of analyzing this transformation for non-natural systems has been described. This current study describes (1) the Michaelis–Menten characterization of 2,2-diphenyethyl glucosinolate and (2) a parallel evaluation of this analogue and the natural analogue glucotropaeolin to evaluate effects of pH and temperature on rates of hydrolysis and product(s) formed. Methods described in this study provide the ability to simultaneously and independently analyze the kinetics of multiple reaction components. An unintended outcome of this work was the development of a modified Lambert W(x) which includes a parameter to account for the thermal denaturation of enzyme. The results of this study demonstrate that the action of Sinapis alba myrosinase on natural and non-natural glucosinolates is consistent under the explored range of experimental conditions and in relation to previous accounts.

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.

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.

(BIS) UREA AND (BIS) THIOUREA COMPOUNDS AS EPIGENIC MODULATORS OF LYSINE-SPECIFIC DEMETHYLASE 1 AND METHODS OF TREATING DISORDERS

The invention provides for novel (bis)urea and (bis)thiourea compounds which are inhibitors of lysine- specific demethylase 1 (LSD1). Such compounds may be used to treat disorders, including cancer.

(Bis)urea and (Bis)thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators

The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 overexpression is thought to contribute to the development of cancer. W

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.

Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts

(Chemical Equation Presented) A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide and triethylamine. Utilizing this protocol, we have prepared 19-alkyl- and arylisothiocyanates in moderate to excellent yield.