15093-36-4

Usage

Uses

Used in Pharmaceutical Industry:
1-ISO-PROPYL-3-PHENYL-2-THIOUREA is used as a drug candidate for cancer treatment due to its ability to inhibit key enzymes involved in tumor growth.
Used in Organic Synthesis:
1-ISO-PROPYL-3-PHENYL-2-THIOUREA is used as a reagent in organic synthesis, contributing to the development of various chemical compounds.
Used in Drug Development for Skin Disorders and Inflammatory Diseases:
1-ISO-PROPYL-3-PHENYL-2-THIOUREA is used as a potential treatment for skin disorders and inflammatory diseases, leveraging its pharmaceutical properties for therapeutic applications.

InChI:InChI=1/C10H14N2S/c1-8(2)11-10(13)12-9-6-4-3-5-7-9/h3-8H,1-2H3,(H2,11,12,13)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 75-31-0 isopropylamine 
• 80306-43-0 [3-Isopropyl-6-phenyl-3,6-dihydro-[1,3]thiazin-(2E)-ylidene]-phenyl-amine 
• 2253-73-8 isopropyl isothiocyanate 
• 62-53-3 aniline 

Downstream Products

• 65672-90-4 (3-isopropyl-[1,3]thiazetidin-2-ylidene)-phenyl-amine 
• 58151-15-8 isopropyl-(3-phenyl-[1,3]thiazetidin-2-ylidene)-amine 
• 130256-08-5 2-isopropyl-4-phenyl-3-thiono-1,2,4-thiadiazolidin-5-one 
• 1019107-95-9 3-isopropyl-1-phenyl-5-[(E)-1-phenylmethylidene]-2-thioxoimidazolidin-4-one 
• 1158081-14-1 C₁₁H₁₄N₄O 
• 1394822-69-5 (E)-4-methoxyphenyl N'-isopropyl-N-phenylcarbamimidate 
• 19895-44-4 1-phenyl-3-i-propylurea 
• 347908-79-6 N-(4-iodophenyl)-N’-isopropylurea 
• 3056-73-3 cinnamanilide 
• 129226-15-9 5-[(E)-Isopropylimino]-4-phenyl-4,5-dihydro-[1,2,4]thiadiazol-3-ylamine 
• 28291-71-6 N-isopropylbenzo[d]thiazol-2-amine 
• 14041-89-5 N-isopropyl-N'-phenylcarbodiimide 

Relevant academic research and scientific papers

Synthesis, stereochemistry determination, pharmacological studies and quantum chemical analyses of bisthiazolidinone derivative

A new compound (3) bisthaizolidinone derivative was synthesized by Knoevenagel condensation reaction. The structure of synthesized compound was elucidated by different spectral techniques and X-ray diffraction studies. The stereochemistry of the compound

Antileishmanial thioureas: Synthesis, biological activity and in Silico evaluations of new promising derivatives

Leishmaniasis is a neglected tropical disease caused by protozoan parasites belonging to the genus Leishmania. Currently, the drugs available for treatment of this disease present high toxicity, along with development of parasite resistance. In order to overcome these problems, efforts have been made to search for new and more effective leishmanicidal drugs. The aim of this study was to synthesize and investigate the leishmanicidal effect of N,N′-disubstituted thioureas against Leishmania amazonensis, with evaluation of their in silico pharmacokinetics and toxicity profiles. Our results showed that different thioureas could be obtained in high to moderate yields using simple reaction conditions. Nine thiourea derivatives (3e, 3i, 3k, 3l, 3p, 3q, 3v, 3x and 3z) were active against parasite promastigotes (IC50 21.48–189.10μM), with low cytotoxicity on mice peritoneal macrophages (CC50>200μM), except for thiourea 3e (CC50=49.22μM). After that, the most promising thioureas (3k, 3l, 3p, 3q and 3v) showed IC50 ranging from 70 to 150μM against L. amazonensis amastigotes in infected macrophages. Except for thiourea 3p, the leishmanicidal activity of the derivatives were independent of nitric oxide (NO) production. Thioureas 3q and 3v affected promastigotes cell cycle without disturbing the mitochondrial membrane potential. Furthermore, our derivatives showed satisfactory theoretical absorption, distribution, metabolism, excretion, toxicity (ADMET) properties. These data indicate that thiourea derivatives are good candidates as leading compounds for the development of new leishmanicidal drugs.

Synthesis of thiazolidines via regioselective addition of unsymmetric thioureas to maleic acid derivatives

A wide range of unsymmetric thioureas has been studied in reaction with N-arylmaleimides and maleic anhydride. The regioselectivity of the addition depends not only on steric factors but on both solvent polarity and type of maleic acid derivative (imide o

A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents

The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.

Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells

Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.

Ultrasound-promoted scavenging: A rapid parallel purification for solution phase combinatorial synthesis

Ultrasound irradiation enhances the mass transfer and reaction rate in scavenging, avoiding the trouble of time-consuming purification procedure in solution-phase parallel synthesis. An application of this technique is demonstrated in the scavenging of excess isothiocyanates from reaction mixtures.

Structure and hydrogen bonding of solid N1-alkyl-N2-arylthioureas. 13C CP/MAS, IR and semi-empirical AM1 studies

Seven crystalline N1-alkyl-N2-arylthioureas were studied by 13C CP/MAS NMR and by IR spectroscopy. The double set of signals in 13C CP/MAS spectra indicates that molecules of N1-ethyl-N2-(3-methylphenyl)thiourea and N1-ethyl-N2-(4-methylphenyl)thiourea are crystallographically non-equivalent. N1-Propene-N1-phenylthiourea forms cyclic dimers with two N2-H...S hydrogen bonds, as confirmed recently by x-ray diffraction. The broad vNH maxima at 3175-3295 cm-1 in the IR spectra indicate that in other thioureas both N1-H and N2-H protons are involved in hydrogen bonding and that the non-bonded N1-H proton in cyclic dimers of N1-propenethioureas is probably an exception. Semi-empirical AM1 calculations showed that the N2-H proton is more positively charged than the N1-H proton and therefore should be preferentially involved in N2-H...S hydrogen bonds.