2627-27-2

Usage

Uses

3-Phenylpropyl isothiocyanate is an isothiocyanate inducer of phase II detoxifying enzymes.

InChI:InChI=1/C10H11NS/c12-9-11-8-4-7-10-5-2-1-3-6-10/h1-3,5-6H,4,7-8H2

Upstream product

• 861572-97-6 μ-disulfido-1,2-dithio-dicarbonic acid bis-(3-phenyl-propylamide) 
• 141-52-6 sodium ethanolate 
• 463-71-8 thiophosgene 
• 30684-05-0 3-phenylpropylamine hydrochloride 
• 31596-17-5 Triethylammonium-3-phenylpropyldithiocarbamat 
• 2038-57-5 3-Phenylpropan-1-amine 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 75-15-0 carbon disulfide 

Downstream Products

• 15093-43-3 N-phenyl-N'-(3-phenylpropyl)thiourea 
• 137915-13-0 S--L-cysteine 
• 149485-04-1 N-(3-Phenylpropyl)-N'-(2-thiazolyl)thiourea 
• 876066-59-0 C₁₉H₂₀Cl₂N₂O₂S 
• 709652-96-0 9-deoxo-9-dihydro-9a-(N'-(3-phenylpropyl)thiocarbamoyl-γ-aminopropyl)-9a-aza-9a-homoerythromycin A 
• 709653-35-0 5-O-desosaminyl-9-deoxo-9-dihydro-9a-[N'-(β-cyanoethyl)-N'-(3-phenylpropyl)thiocarbamoyl-γ-aminopropyl]-9a-aza-9a-homoerythronolide A 
• 1489288-27-8 1-(4-chlorophenoxyacetyl)-4-phenylpropyl-thiosemicarbazide 

Relevant academic research and scientific papers

T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates

A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.

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.

The role of 5-arylalkylamino- and 5-piperazino- moieties on the 7-aminopyrazolo[4,3-d]pyrimidine core in affecting adenosine A1 and A2A receptor affinity and selectivity profiles

New 7-amino-2-phenylpyrazolo[4,3-d]pyrimidine derivatives, substituted at the 5-position with aryl(alkyl)amino- and 4-substituted-piperazin-1-yl- moieties, were synthesized with the aim of targeting human (h) adenosine A1 and/or A2A receptor subtypes. On the whole, the novel derivatives 1–24 shared scarce or no affinities for the off-target hA2B and hA3 ARs. The 5-(4-hydroxyphenethylamino)- derivative 12 showed both good affinity (Ki = 150 nM) and the best selectivity for the hA2A AR while the 5-benzylamino-substituted 5 displayed the best combined hA2A (Ki = 123 nM) and A1 AR affinity (Ki = 25 nM). The 5-phenethylamino moiety (compound 6) achieved nanomolar affinity (Ki = 11 nM) and good selectivity for the hA1 AR. The 5-(N4-substituted-piperazin-1-yl) derivatives 15–24 bind the hA1 AR subtype with affinities falling in the high nanomolar range. A structure-based molecular modeling study was conducted to rationalize the experimental binding data from a molecular point of view using both molecular docking studies and Interaction Energy Fingerprints (IEFs) analysis. (Figure presented.).

Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me4N)SCF3

A highly efficient, selective, and rapid transformation of primary amines and diamines to isothiocyanates and cyclic thioureas is disclosed. As opposed to established approaches that employ toxic or volatile electrophilic liquids and require reaction control (i.e., slow addition, cooling), this protocol utilizes the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is characterized by operational simplicity, high speed, efficiency, high functional group tolerance, and late-stage applicability. The byproducts are solids, allowing isolation of the target compounds by filtration.

Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group

Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure-activity relationships.

SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region)

Certain derivatives and analogues of capsazepine are potent in vitro inhibitors of bronchoconstriction in human small airways. During an investigation of the dependency of the potency on the structural features of the capsazepinoids in the thiourea moiety (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region), it was revealed that capsazepinoids with a thiourea or an amide link between the B-ring and the C-region in general have a good bronchorelaxing activity, while urea is a less attractive choice. Further, it was shown that 1,2,3,4-tetrahydroisoquinolines with a 2-(phenyl)ethyl derivative as the C-region are considerably more potent than those with an octyl group, while 2,3,4,5-tetrahydro-1H-2-benzazepines were found to be more insensitive to the nature of the C-region.

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.

Bronchorelaxing compounds

A compound of the general formula (I) including its pharmaceutically acceptable acid addition salts wherein A is CHR9, wherein R9 is H, C1-C6 alkyl; n is 1-3; B is CHR10, wherein R10 is H, C1-C6 alkyl; m is 1 or 2; D is O or S or optionally NR16, wherein R16 is H, C1-C6 alkyl or C2-C6 acyl; E is CR11R12 or NR13, wherein R11 and R12 are, independent of each other, H or C1-C6 alkyl, R13 is H or C1-C6 alkyl; F is C1-C18 alkyl which may be mono- or di-unsaturated and/or substituted, is useful in treating and preventing pulmonary disease characterized by bronchoconstriction. Also disclosed are pharmaceutical compositions comprising the compound and methods for their manufacture.

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.