29336-07-0

Upstream product

• 463-71-8 thiophosgene 
• 104-94-9 4-methoxy-aniline 
• 100-01-6 4-nitro-aniline 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 2420-60-2 O-phenyl N-(4-nitrophenyl)thiocarbamate 
• 2131-61-5 p-nitrophenyl isothiocyanate 

Downstream Products

• 40387-34-6 N-(4-methoxyphenyl)-N′-(4-nitrophenyl)urea 
• 22007-38-1 O-ethyl N-(4-methoxyphenyl)thiocarbamate 
• 13806-75-2 N-(4-nitrophenyl)thiocarbamic acid O-ethyl ester 
• 1227-45-8 1,3-bis-(p-methoxyphenyl)thiourea 
• 29264-14-0 N¹-(4-aminophenyl)-N²-(4-methoxyphenyl)thiourea 

Relevant academic research and scientific papers

Design, synthesis and molecular modeling study of certain VEGFR-2 inhibitors based on thienopyrimidne scaffold as cancer targeting agents

Different series of novel thieno [2,3-d]pyrimidine derivative (9a-d,10a-f,l,m and 15a-m) were designed, synthesized and evaluated for their ability to in vitro inhibit VEGFR-2 enzyme. Also, the cytotoxicity of the final compounds was tested against a panel of 60 different human cancer cell lines by NCI. The VEGFR-2 enzyme inhibitory results revealed that compounds 10d, 15d and 15 g are among the most active inhibitors with IC50 values of 2.5, 5.48 and 2.27 μM respectively, while compound 10a remarkably showed the highest cell growth inhibition with mean growth inhibition (GI) percent of 31.57%. It exhibited broad spectrum anti-proliferative activity against several NCI cell lines specifically on human breast cancer (T7-47D) and renal cancer (A498) cell lines of 85.5% and 77.65% inhibition respectively. To investigate the mechanistic aspects underlying the activity, further biological studies like flow cytometry cell cycle together with caspase-3 colorimetric assays were carried on compound 10a. Flow cytometric analysis on both MCV-7 and PC-3 cancer cells revealed that it induced cell-cycle arrest in the G0-G1phase and reinforced apoptosis via activation of caspase-3. Furthermore, molecular modeling studies have been carried out to gain further understanding of the binding mode in the active site of VEGFR-2 enzyme and predict pharmacokinetic properties of all the synthesized inhibitors.

Ph3P/I2-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates

A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2 system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.

Convenient synthesis of unsymmetrical N,N′-disubstituted thioureas in water

A simple and convenient two-step method has been developed and used to synthesise 25 (4 of which are novel) unsymmetrical N,N′-disubstituted thioureas in water. Alkylamines or variously substituted arylamines reacted smoothly with phenyl chlorothionoformate at room temperature to form thiocarbamates, which were then reacted with another alkyl- or arylamine in water at reflux to afford the unsymmetrical N,N′-disubstituted thioureas in good to excellent yields. Mild conditions, simple work-up, high yields as well as using water as solvent are the major advantages of the method.

Synthesis and characterisation of [(en)2Co]3+ complexes coordinated by substituted thiourea ligands

Substituted thiourea ligands bind in a bidentate manner forming a four-membered ring through the sulfur atom and a deprotonated thiourea nitrogen atom when reacted with [(en)2Co(OSO2CF3)2]+ in tetramethylene sulfone. Reaction of unsymmetrical ligands results in the formation of coordination isomers, some of which can be separated by column chromatography using Sephadex SPC-25. Coordination isomers are easily distinguishable based on visible and 1H NMR spectroscopy . Twelve para-substituted and one meta-substituted ligands were studied: N,N′-dibenzylthiourea (1a); N-(R)phenyl-N′-benzylthiourea R≤H (2a), NO2 (2b), CH3 (2c); N-(R)phenyl-N′-(R′)phenylthiourea R, R′: H, H (3a), H, CH3 (3b), OCH3, NO2 (3c), CH3, NO2 (3d); N-methyl-N′-(R)phenylthiourea R≤H (4a), CH3 (4b), OCH3 (4c), NO2 (4d), 3-CH3 (4e). The solid state structure (X-ray) of one isomer of Co-4a as its perchlorate salt confirms the coordination mode suggested by 1H NMR spectroscopy and shows that the Co-N bond trans to the coordinated thiourea sulfur induces a structural trans effect of 0.019A.

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.

The Kinetics and Mechanism of Aminolysis of Isothiocyanates

A study of the kinetics of aminolysis of p-nitrophenyl isothiocyanate by n-butylamine, benzylamine, dibenzylamine, p-anisidine, m-toluidine, N-methylaniline, and p-chloroaniline in diethyl ether and isooctane as solvents has shown that many of the reactio

Identification of a Baker-type Mechanism in Additions to p-Nitrophenyl Isothiocyanate in Diethyl Ether Solution

Kinetic evidence is presented which strongly suggests that in the diethyl ether solution the aminolysis of p-nitrophenyl isothiocyanate proceeds via a mechanism involving a 1:1-addition intermediate which undergoes catalyzed prototropic rearrangement to t