55805-95-3

Usage

Preparation

Preparation by Friedel–Crafts acylation of p-nitrophe-nol with propionyl chloride in nitrobenzene in the presence of aluminium chloride (36%) Also obtained by Fries rearrangement of p-nitrophenyl propionate (m.p. 63–64°) in nitrobenzene in the presence of aluminium chloride at 125° for 5 h (23%) Preparation by reaction of boron trichloride with 2-methoxy-5-nitropropiophe-none in methylene chloride, first at ?78°, then at r.t. for 14 h (92%). Also obtained by nitration of o-hydroxypropiophenone (23%), in acetic acid with fuming nitric acid, first at 0°, then at 60°Also obtained by alkaline hydrolysis of 3-methyl-6-nitrochromone (m.p. 147–148°) (85%).

Upstream product

• 100-02-7 4-nitro-phenol 
• 79-03-8 propionyl chloride 
• 610-99-1 1-(2-Hydroxy-phenyl)-propan-1-on 
• 5561-92-2 1-(2-methoxyphenyl)propan-1-one 
• 682320-25-8 1-(2-methoxy-5-nitrophenyl)propan-1-one 

Downstream Products

• 87699-50-1 1-(2-{2-[Bis-(2-chloro-ethyl)-amino]-ethoxy}-5-nitro-phenyl)-propan-1-one; hydrochloride 
• 87699-36-3 1-[2-(2-{(2-Chloro-ethyl)-[2-(4-nitro-2-propionyl-phenoxy)-ethyl]-amino}-ethoxy)-5-nitro-phenyl]-propan-1-one; hydrochloride 
• 88521-74-8 ethyl 4-nitro-2-propionylphenoxyacetate 
• 88521-65-7 4-nitro-2-propionylphenoxyacetic acid 
• 508210-97-7 1-[2-(2-Chlorobenzyloxy)-5-nitrophenyl]propan-1-one 
• 508211-15-2 1-[2-(3,3-Diphenylpropoxy)-5-nitrophenyl]propan-1-one 
• 508210-84-2 1-[2-(4-Isopropylbenzyloxy)-5-nitrophenyl]propan-1-one 
• 508210-82-0 1-[2-(4-tert-Butylbenzyloxy)-5-nitrophenyl]propan-1-one 
• 508210-76-2 1-[2-(Benzhydryloxy)-5-nitrophenyl]propan-1-one 
• 508211-07-2 1-[2-Neopentyloxy-5-nitrophenyl]propan-1-one 
• 119197-67-0 methyl (4-nitro-2-propionylphenoxy)acetate 

Relevant academic research and scientific papers

Structure-Activity Relationships of Nitro-Substituted Aroylhydrazone Iron Chelators with Antioxidant and Antiproliferative Activities

Aroylhydrazone iron chelators such as salicylaldehyde isonicotinoyl hydrazone (SIH) protect various cells against oxidative injury and display antineoplastic activities. Previous studies have shown that a nitro-substituted hydrazone, namely, NHAPI, displayed markedly improved plasma stability, selective antitumor activity, and moderate antioxidant properties. In this study, we prepared four series of novel NHAPI derivatives and explored their iron chelation activities, anti- or pro-oxidant effects, protection against model oxidative injury in the H9c2 cell line derived from rat embryonic cardiac myoblasts, cytotoxicities to the corresponding noncancerous H9c2 cells, and antiproliferative activities against the MCF-7 human breast adenocarcinoma and HL-60 human promyelocytic leukemia cell lines. Nitro substitution had both negative and positive effects on the examined properties, and we identified new structure-activity relationships. Naphthyl and biphenyl derivatives showed selective antiproliferative action, particularly in the breast adenocarcinoma MCF-7 cell line, where they exceeded the selectivity of the parent compound NHAPI. Of particular interest is a compound prepared from 2-hydroxy-5-methyl-3-nitroacetophenone and biphenyl-4-carbohydrazide, which protected cardiomyoblasts against oxidative injury at 1.8 ± 1.2 μM with 24-fold higher selectivity than SIH. These compounds will serve as leads for further structural optimization and mechanistic studies.

Rate of Enolate Formation Is Not Very Sensitive to the Hydrogen Bonding Ability of Donors to Carboxyl Oxygen Lone Pair Acceptors; A Ramification of the Principle of Non-Perfect Synchronization for General-Base-Catalyzed Enolate Formation

Two series of structures (1 and 2) possessing intramolecular hydrogen bonds to the lone-pair electrons of carbonyl oxygens have been examined to reveal the influence of the pKa of the hydrogen-bond donor on the rate of general-base-catalyzed enolate formation. The geometry of the hydrogen bonds is well accepted to be appropriate for intramolecular hydrogen-bond formation. Yet, as revealed by Bronsted plots, both series show very little dependence of the rate of enolate formation on the hydrogen-bond donor ability. The intramolecular hydrogen bonds give rate enhancements only on the order of 10-100-fold, and corrected Bronsted α-values are slightly below 0.1. The results can be understood by interpreting them in light of the Principle of Non-Perfect Synchronization. The results are consistent with the proton transfer occurring through an asynchronous transition state with the developing negative charge localized on carbon. We postulate that catalysts of enolate formation will be most effective if the binding groups are focused on stabilizing negative charge that is forming on the enolate carbon rather than on the enolate oxygen.

BENZOFURAN DERIVATIVES. I. ON THE EFFECTS OF SUBSTITUENTS IN BENZOFURAN SYNTHESES.

The Roessing's reaction of 4-substituted 2-acylphenoxyacetic acids give a mixture of benzofurans and 2-benzofurancarboxylic acids. The relative yields of benzofurans and 2-benzofurancarboxylic acids depend on the substituents on the benzene ring of the 2-acylphenoxyacetic acids. Electron-withdrawing substituents such as nitro groups favor the formation of 2-benzofurancarboxylic acids. On the other hand, the formation of benzofurans is favored by the steric hindrance of 2-acyl groups in the reaction of 2-acyl-4-nitrophenoxyacetic acids with anhydrous sodium acetate and acetic anhydride.