3034-94-4

Usage

Uses

Used in Organic Synthesis:
3-Nitrophenylacetylene is used as a building block in organic synthesis for its high reactivity and versatility. It is particularly valuable in the creation of complex organic molecules and compounds.
Used in Pharmaceutical Industry:
3-Nitrophenylacetylene is used as a key ingredient in the manufacture of pharmaceuticals. Its reactivity allows for the synthesis of various drug molecules, contributing to the development of new medications and therapies.
Used in Agrochemical Industry:
In the agrochemical industry, 3-Nitrophenylacetylene is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity enables the production of effective and targeted chemical compounds for agricultural applications.
Used in Performance Materials:
3-Nitrophenylacetylene is used in the production of performance materials, such as advanced polymers and composites. Its unique properties contribute to the development of materials with enhanced properties, such as strength, durability, and thermal stability.

InChI:InChI=1/C8H5NO2/c1-2-7-4-3-5-8(6-7)9(10)11/h1,3-6H

Upstream product

• 530-85-8 3-(2-nitrophenyl)-2-propynoic acid 
• 103606-71-9 3-(3-nitrophenyl)-2-propyn-1-ol 
• 33432-52-9 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol 
• 4996-15-0 3-(3-nitrophenyl)propynoic acid 
• 7732-18-5 water 
• 121-90-4 m-nitrobenzoic acid chloride 
• 121-89-1 3-Nitroacetophenone 
• 645-00-1 m-iodonitrobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 21047-57-4 diethyl (1-diazo-2-oxopropyl)phosphonate 
• 99-61-6 3-nitro-benzaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 444681-65-6 1,1-dibromo-2-(3-nitrophenyl)ethene 
• 98-86-2 acetophenone 

Downstream Products

• 964-91-0 5-(3-nitrophenyl)-3-phenylisoxazole 
• 121-89-1 3-Nitroacetophenone 
• 134682-50-1 1-(3-nitrophenyl)-2-(4-nitrophenyl)acetylene 
• 2765-15-3 1-nitro-3-[(3-nitrophenyl)ethynyl]benzene 
• 122540-43-6 3,3'-bis<β-(phenyltelluro)vinyl>azobenzene 
• 122540-45-8 4,4'-bis<β-(phenyltelluro)vinyl>azobenzene 
• 110296-08-7 (Z)-3-aminostyryl phenyl telluride 
• 42254-91-1 4,4'-divinylazobenzene 
• 110210-18-9 1-(4'-methylphenylsulfonyl)-2-iodo-2-(3'-nitrophenyl)ethene 
• 940-13-6 1-(2-bromoethynyl)-4-nitrobenzene 
• 54060-30-9 3-acetylenephenylamine 
• 31661-56-0 1,4-bis(3-nitrophenyl)-1,3-butadiyne 
• 89039-15-6 C₈H₆⁽²⁾HNO₂ 
• 86440-77-9 1-bromo-2-(3-nitrophenyl)acetylene 

Relevant academic research and scientific papers

A METHOD FOR THE PREPARATION OF TERMINAL ACETYLENES

A new pathway is proposed for the preparation of terminal acetylenes entailing the condensation of acid chlorides with phenylacetylene, isomerization of the acetylenic ketones with displacement of the oxo group and triple bond in the ketoacetylenic fragment, and subsequent alkaline cleavage of the isomerized ketones.

Topochemical polymerization of unsymmetrical aryldiacetylene supramolecules with nitrophenyl substituents utilizing C-H...π interactions

Diacetylenes are versatile building blocks, in which many functional groups can be incorporated for the construction of new materials with desirable properties. In this study, 6-(p or m-nitrophenyl)-3,5-hexadiyne-1-ol (4a or 4b) containing nitrophenyl groups (host) and 2-hydroxyethyl groups (guest) in different diacetylene terminals were designed to establish an ordered supramolecular assembly that is complied with the strict requirements for the topochemical polymerization of diacetylenes. Crystal film and bulk crystals of compound 4b were obtained successfully by cast film and re-precipitation methods. Both of these could photopolymerize to the corresponding regular poly(diacetylene) polymer, as evidenced by UV-vis, IR, FL and Raman spectroscopy. The electrochemical properties and behaviors of 4a and 4b were also investigated, and the results show that the differences between the para and meta positions of the mono-phenylacetylene substituents probably result from the topochemical polymerization. Thus, m-nitrophenylbutadiyne derivatives with sizeable C-H...π interactions seemed to be effective for the formation of a polymerizable packing, which is appropriate for topochemical polymerization.

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

Preparation method of m-aminophenylacetylene

The invention discloses a preparation method of m-aminophenylacetylene, belonging to the technical field of organic synthesis. The method comprises the following steps of: subjecting m-nitroacetophenone serving as a raw material to reacting with triethyl phosphite under the action of a catalyst, continuously converting the m-nitroacetophenone into enol form, and condensing the enol form with the triethyl phosphite to obtain condensation ester, wherein the condensation ester is easy to separate and high in purity, m-nitrophenylacetylene is generated from the ester under the action of strong base, and m-aminophenylacetylene is generated from the ester through reduction. Compared with an acetophenone chlorination method, the method of the invention has the advantages that phosphorus oxychloride does not need to be used for changing oxygen of the m-nitroacetophenone into chlorine, pollution is small, purity is high ( 98% or more), the use of high-pollution raw material reagents is avoided, operation is simple, the environment-friendly effects are realized, and industrial production can be conveniently realized.

Preparation method of acetenyl aniline

The invention discloses a preparation method of acetenyl aniline, wherein the preparation method comprises the following steps: by using nitroethylbenzene as a raw material and MBr-MBrO3-H2SO4 (M=Na or K) as a bromination reagent, carrying out free radical bromination reaction to prepare 1,1-dibromo-1-(nitrophenyl)ethane, carrying out elimination reaction under the action of alkali to obtain nitrophenylacetylene, and finally, carrying out Fe/HCl reduction to obtain acetenyl aniline. The preparation method provided by the invention has the advantages of cheap and easily available raw materials, simple and safe operation, good reaction selectivity, high product yield, less emission of three wastes and the like.

Synthesis and application of novel triazole compound

The invention discloses a novel triazole compound as shown in figure 1 and an application of the novel triazole compound as a protein arginine methyltransferase 5 inhibitor, and discloses an application of the compound in prevention and/or treatment of cancer-related diseases caused by abnormal activity of protein arginine methyltransferase 5.

A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity

Inhibiting the protein-protein interaction (PPI) between the transcription factor Nrf2 and its repressor protein Keap1 has emerged as a promising strategy to target oxidative stress in diseases, including central nervous system (CNS) disorders. Numerous non-covalent small-molecule Keap1-Nrf2 PPI inhibitors have been reported to date, but many feature suboptimal physicochemical properties for permeating the blood-brain barrier, while others contain problematic structural moieties. Here, we present the first side-by-side assessment of all reported Keap1-Nrf2 PPI inhibitor classes using fluorescence polarization, thermal shift assay, and surface plasmon resonance - and further evaluate the compounds in an NQO1 induction cell assay and in counter tests for nonspecific activities. Surprisingly, half of the compounds were inactive or deviated substantially from reported activities, while we confirm the cross-assay activities for others. Through this study, we have identified the most promising Keap1-Nrf2 inhibitors that can serve as pharmacological probes or starting points for developing CNS-active Keap1 inhibitors.

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Rational Design, synthesis and biological evaluation of novel triazole derivatives as potent and selective PRMT5 inhibitors with antitumor activity

Protein arginine methyltransferase 5 (PRMT5) is responsible for the mono-methylation and symmetric dimethylation of arginine, and its expression level and methyl transferring activity have been demonstrated to have a close relationship with tumorigenesis, development and poor clinical outcomes of human cancers. Two PRMT5 small molecule inhibitors (GSK3326595 and JNJ-64619178) have been put forward into clinical trials. Here, we describe the design, synthesis and biological evaluation of a series of novel, potent and selective PRMT5 inhibitors with antiproliferative activity against Z-138 mantle cell lymphoma cell line. Among them, compound C_4 exhibited the highest potency with enzymatic and cellular level IC50 values of 0.72 and 2.6 μM, respectively, and displayed more than 270-fold selectivity toward PRMT5 over several other isoenzymes (PRMT1, PRMT4 and PRMT6). Besides, C_4 demonstrated obvious cell apoptotic effect while reduced the cellular symmetric arginine dimethylation levels of SmD3 protein. The potency, small size, and synthetic accessibility of this compound class provide promising hit scaffold for medicinal chemists to further explore this series of PRMT5 inhibitors.

Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs

Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.