15845-62-2

Usage

Uses

Used in Pharmaceutical Industry:
4-IODOPHENYL ISOCYANATE is used as a key intermediate for the synthesis of various pharmaceutical compounds, such as silicon-stereogenic silicon-bridged arylpyridinones, N-(4-iodophenyl)cholesteryl-3-carbamate, and N-(4-iodophenyl)pregnenolone-3-carbamate. These compounds have potential applications in the treatment of various medical conditions and diseases.
Used in Chemical Synthesis:
4-IODOPHENYL ISOCYANATE is used as a versatile building block in the synthesis of a wide range of organic compounds. Its reactivity and unique structure make it a valuable component in the development of new materials and products across various industries, including pharmaceuticals, agrochemicals, and specialty chemicals.

Preparation

To a solution of triphosgene (3.0 g, 10 mmol) and triethylamine (2.02 g, 20 mmol) in dry benzene (30 mL), a solution of 4-iodoaniline (4.3 g, 20 mmol) in dry benzene (15 mL) was added over 20 min. During the course of the addition, the temperature of the reaction mixture was increased from ambient to reflux temperature. After refluxing for 3 h, the reaction mixture was filtered. The filtrate was concentrated to obtain a residue, which was subjected to distillation under reduced pressure to afford a colorless liquid. Yield 2.21 g (45.2%).

InChI:InChI=1/C7H4INO/c8-6-1-3-7(4-2-6)9-5-10/h1-4H

Upstream product

• 75-44-5 phosgene 
• 540-37-4 p-aminoiodobenzene 
• 503-38-8 trichloromethyl chloroformate 
• 619-58-9 4-iodobenzoic acid 
• 1711-02-0 4-iodobenzoic acid chloride 
• 22693-31-8 azido(4-iodophenyl)methanone 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 77774-39-1 1-(N-ethoxycarbonylamino)-4-iodobenzene 
• 25434-10-0 N,N-diethyl-N′-(4-iodophenyl)urea 
• 22546-49-2 C₈H₁₀IN₃O 
• 124420-90-2 N-4-iodophenyl-N'-4-pyridylurea 
• 86781-29-5 1,1-Dibutyl-3-(4-iodo-phenyl)-urea 
• 86764-46-7 1,1-Dibenzyl-3-(4-iodo-phenyl)-urea 

Relevant academic research and scientific papers

Water-Proton Relaxivities of Radical Nanoparticles Self-Assembled via Hydration or Dehydration Processes

Nanoparticles capable of accumulating in tumor tissues are promising materials for tumor imaging and therapy. In this study, two radical nanoparticles (RNPs), denoted as 1 and 2, composed of self-assembled ureabenzene derivatives possessing one or two amp

Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer

Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel urea-based compounds with cytotoxicity against selected cell lines and with the ability to cross the blood-brain barrier in vivo. We have synthesized and analyzed a library of more than 40 compounds to elucidate the key features responsible for the observed activity. We have also identified FGFR1 as a molecular target that is affected by the presence of these compounds, confirming our data using in silico model. Overall, we envision that these compounds can be further developed for the potential treatment of metastatic breast cancer.

Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes via Amidyl Radical Cyclization

An electrochemical synthesis of oxazol-2-ones and imidazol-2-ones has been developed via 5-exo-dig cyclization of propargylic carbamates- and ureas-derived amidyl radicals. The electrosynthesis relies on the dual function of 2,2,6,6-tetramethylpiperidin- 1-yl)oxyl (TEMPO) as a redox mediator for amidyl radical formation and an oxygen atom donor. The reactions are conducted under mild conditions using a simple setup and provide convenient access to functionalized oxazol-2-ones and imidazol-2-ones from readily available materials.

Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78–22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.

Electrochemical C?H/N?H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles

Indoles and azaindoles are among the most important heterocycles because of their prevalence in nature and their broad utility in pharmaceutical industry. Reported herein is an unprecedented noble-metal- and oxidant-free electrochemical method for the coupling of (hetero)arylamines with tethered alkynes to synthesize highly functionalized indoles, as well as the more challenging azaindoles.

Mono- and triiodophenyl isocyanate as radiopacifying agents for methacrylate-based copolymers; Biocompatibility and non-toxicity

New radiopaque acrylic copolymers were prepared via the copolymerization of methyl methacrylate (MMA) and acrylic acid (AA). The copolymers were made radiopaque through the reaction of carboxylic acid groups with 4-iodophenyl isocyanate and 3,4,5-triiodop

Rhenium-catalyzed C-H aminocarbonylation of azobenzenes with isocyanates

The first C-H aminocarbonylation of azobenzenes with isocyanates is achieved by using rhenium-catalysis, which provides an expedient and atom-economical access to varied o-azobenzamides from readily available starting materials. The reaction efficiency can be enhanced by the catalytic use of sodium acetate via accelerated C-H bond activation.

Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors

A number of 1,2-benzisothiazol-3-one derivatives were prepared through structural modification of the original compound from high-throughput screening. Some analogues (e.g., 6b, 6r, 6s and 6w) were identified as novel and potent caspase inhibitors with IC50 of nanomolar. Structure-activity relationship (SAR) studies for caspase-3 inhibition were evaluated in vitro. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The present small molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.

1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: Structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain

1,3-Disubstituted ureas possessing a piperidyl moiety have been synthesized to investigate their structure-activity relationships as inhibitors of the human and murine soluble epoxide hydrolase (sEH). Oral administration of 13 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors in mice revealed substantial improvements in pharmacokinetic parameters over previously reported 1-adamantylurea based inhibitors. For example, 1-(1-(cyclopropanecarbonyl) piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (52) showed a 7-fold increase in potency, a 65-fold increase in Cmax, and a 3300-fold increase in AUC over its adamantane analogue 1-(1-adamantyl)-3-(1-propionylpiperidin-4-yl) urea (2). This novel sEH inhibitor showed a 1000-fold increase in potency when compared to morphine by reducing hyperalgesia as measured by mechanical withdrawal threshold using the in vivo carrageenan induced inflammatory pain model.

Comparison of base-promoted and self-catalyzed conditions in the synthesis of isocyanates from amines using triphosgene

Comparison of base-promoted and self-catalyzed conditions for the synthesis of isocyanates from amines and triphosgene shows no advantage in using an amine base in the majority of cases. The workup and isolation of the product is simplified under base-free conditions. Yields of between 50 and 90% after distillation were common. Only acid-sensitive substrates need a base catalyst. Copyright Taylor & Francis Group, LLC.