3550-21-8

Usage

Uses

Used in Organic Synthesis:
Benzhydril isothiocyanate is used as a key intermediate in the synthesis of various organic compounds, particularly for the preparation of pharmaceuticals and agrochemicals. Its high reactivity allows for the formation of a wide range of products through nucleophilic addition and other chemical reactions.
Used in Pharmaceutical Industry:
Benzhydril isothiocyanate is used as a building block for the development of new pharmaceuticals. Its unique chemical properties enable the creation of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, benzhydril isothiocyanate serves as an important intermediate for the synthesis of various agrochemicals, including pesticides and herbicides. Its reactivity allows for the development of effective compounds for crop protection and management.
Used in Cancer Research:
Benzhydril isothiocyanate has been studied for its potential anti-cancer properties. It is used as a research compound to investigate its ability to induce apoptosis in cancer cells, which could lead to the development of new cancer therapies.
Used in Drug Delivery Systems:
To overcome the challenges associated with the high reactivity and potential toxicity of benzhydril isothiocyanate, researchers are developing novel drug delivery systems. These systems aim to improve the compound's delivery, bioavailability, and therapeutic outcomes while minimizing its potential side effects.

InChI:InChI=1/C14H11NS/c16-11-15-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H

Upstream product

• 776-74-9 Bromodiphenylmethane 
• 75-15-0 carbon disulfide 
• 91-00-9 Benzhydrylamine 
• 592-87-0 lead(II) thiocyanate 
• 908093-98-1 diazodiphenylmethane 
• 5961-98-8 thiocyanatochloride 
• 101-81-5 Diphenylmethane 
• 4467-90-7 N-hydroxy-2,2-diphenylacetimidoyl chloride 
• 333-20-0 potassium thioacyanate 
• 91-01-0 1,1-Diphenylmethanol 
• 1147550-11-5 ammonium thiocyanate 
• 14629-59-5 diphenylmethyl trimethylsilyl ether 
• 96185-28-3 (benzhydryloxy)(tert-butyl)dimethylsilane 
• 463-71-8 thiophosgene 

Downstream Products

• 5267-35-6 N-(diphenylmethyl)acetamide 
• 1485-72-9 N-benzoyl-diphenylmethylamine 
• 92192-94-4 benzhydryl-thiourea 
• 21198-25-4 4-benzhydrylthiosemicarbazide 
• 103098-41-5 hydrazine-N,N'-bis-carbothioic acid bis-benzhydrylamide 
• 101288-71-5 1-benzhydryl-3-(2-hydroxy-ethyl)-thiourea 
• 24308-43-8 1-(diphenylmethyl)-3-phenylthiourea 
• 68696-29-7 N-benzhydryl-N'-methyl-thiourea 
• 109814-10-0 morpholine-4-carbothioic acid benzhydrylamide 
• 102458-24-2 1-benzhydryl-3-cyclohexylthiourea 
• 263011-17-2 C₂₉H₃₃N₅O₆S₂ 
• 439093-35-3 C₂₅H₂₅N₅O₆S₂ 
• 263011-18-3 C₂₅H₂₅N₅O₆S₂ 
• 313695-72-6 N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-diphenylmethylthiourea 

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.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

Synthesis methods for isothiocyanate derivative

The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.

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.

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.

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.

Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor

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 biological properties of MIF are closely linked to protein-protein interactions, M

Phosphine-free conversion of alcohols into alkyl thiocyanates using trichloroisocyanuric acid/NH4SCN

A convenient and efficient phosphine-free procedure for the one-pot conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates is described using trichloroisocyanuric acid/NH4SCN.

Selectfluor F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions

A convenient approach for thiocyanation of alcohols has been developed using ammonium thiocyanate as thiocyanating agent in the presence of a catalytic amount of Selectfluor F-TEDA-BF4 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding thiocyanates or isothiocyanates directly in good to high yield under heterogeneous and neutral conditions.

(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.