5425-81-0

Usage

Uses

Used in Organic Synthesis:
2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE is used as a building block in organic synthesis for the creation of various pharmaceutical drugs and fine chemicals. Its presence of both nitro and amino groups allows for a range of chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE is employed as an intermediate in the development of new drugs. Its unique structure and reactivity enable the design and synthesis of novel therapeutic agents with potential applications in medicine.
Used in Dye and Pigment Manufacturing:
2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE is utilized as an intermediate in the production of dyes and pigments. Its chemical properties allow for the creation of a variety of colorants used in different industries, such as textiles, plastics, and printing inks.
Used in Medicine:
2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE has potential applications in the medical field due to its unique properties. It can be used in the development of new pharmaceuticals, including those targeting specific diseases or conditions.
Used in Agriculture:
In agriculture, 2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE may be employed in the development of new agrochemicals, such as pesticides or herbicides, to improve crop protection and yield.
Used in Chemical Research:
2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE is also used in chemical research to explore its properties and reactivity. This can lead to the discovery of new reactions, compounds, or applications in various industries.

InChI:InChI=1/C8H8N2O3.ClH/c9-5-8(11)6-1-3-7(4-2-6)10(12)13;/h1-4H,5,9H2;1H

Upstream product

• 88260-40-6 (4-nitrophenacyl)hexaminium bromide 
• 91147-75-0 C₈H₆BrNO₃*C₆H₁₂N₄ 
• 1386376-84-6 (R)-N-tert-butanesulfinyl 2-(4-nitrophenyl)-2-oxoethylamine 
• 100-19-6 (4-nitrophenyl)ethanone 
• 99-81-0 4-Nitrophenacyl bromide 
• 4740-22-1 2-amino-1-(4-nitro-phenyl)-ethanone 

Downstream Products

• 6857-35-8 4-(4-nitro-phenyl)-1,3-dihydro-imidazole-2-thione 
• 21332-80-9 2-amino-1-[4-(6-chloro-2-methoxy-acridin-9-ylamino)-phenyl]-ethanol 
• 51641-44-2 4-[5-(4-nitro-phenyl)-oxazol-2-yl]-naphthalene-1,8-dicarboxylic acid anhydride 
• 90490-65-6 1-(4-Nitro-phenyl)-2-pyrrol-1-yl-ethanone 
• 115846-57-6 2-(4,5-Dihydro-3H-pyrrol-2-ylamino)-1-(4-nitro-phenyl)-ethanone; hydrochloride 
• 94993-74-5 5-Methyl-4-nitro-2H-pyrazole-3-carboxylic acid [2-(4-nitro-phenyl)-2-oxo-ethyl]-amide 
• 96139-73-0 4-(p-nitrophenyl)-4-imidazoline-2-one 
• 345652-53-1 2-(4-difluoromethylsulfonylphenyl)-5-(4-nitrophenyl)oxazole 
• 94993-84-7 {3-Methyl-5-[2-(4-nitro-phenyl)-2-oxo-ethylcarbamoyl]-1H-pyrazol-4-yl}-carbamic acid tert-butyl ester 
• 90490-69-0 2-(2,5-Dimethyl-pyrrol-1-yl)-1-(4-nitro-phenyl)-ethanone 
• 64748-77-2 2-(2,4-dioxo-imidazolidin-1-ylimino)-N-[2-(4-nitro-phenyl)-2-oxo-ethyl]-acetamide 
• 73286-35-8 2-ethyl-5-(4'-nitrophenyl)oxazole 
• 115846-63-4 3-(4-Nitro-phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole; hydrochloride 
• 73286-36-9 2-Ethyl-5-(4-anilino)oxazole 

Relevant academic research and scientific papers

The reaction of prop-2-ynylsulfonium salts and sulfonyl-protected β-amino ketones to epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles

A novel divergent domino annulation reaction of prop-2-ynylsulfonium salts with sulfonyl-protected β-amino ketones has been developed, affording various epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles in moderate to excellent yields. Prop-2-ynylsulfonium salts act as C2synthons in the reactions providing a promising epoxide-fused skeleton in a single operation with readily accessible starting materials.

Synthesis, characterization, and biological evaluation of new derivatives targeting MbtI as antitubercular agents

Tuberculosis (TB) causes millions of deaths every year, ranking as one of the most dangerous infectious diseases worldwide. Because several pathogenic strains of Mycobacterium tuberculosis (Mtb) have developed resistance against most of the established anti-TB drugs, new therapeutic options are urgently needed. An attractive target for the development of new antitubercular agents is the salicylate synthase MbtI, an essential enzyme for the mycobacterial siderophore biochemical machinery, absent in human cells. A set of analogues of I and II, two of the most potent MbtI inhibitors identified to date, was synthesized, characterized, and tested to elucidate the structural requirements for achieving an efficient MbtI inhibition and a potent antitubercular activity with this class of compounds. The structure-activity relationships (SAR) here discussed evidenced the importance of the furan as part of the pharmacophore and led to the preparation of six new compounds (IV-IX), which gave us the opportunity to examine a hitherto unexplored position of the phenyl ring. Among them emerged 5-(3-cyano-5-(trifluoromethyl)phenyl)furan-2-carboxylic acid (IV), endowed with comparable inhibitory properties to the previous leads, but a better antitubercular activity, which is a key issue in MbtI inhibitor research. Therefore, compound IV offers promising prospects for future studies on the development of novel agents against mycobacterial infections.

Synthesis of a New Phorbazole and Its Derivatives

Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.

READ-THROUGH INDUCER AND PHARMACEUTICAL USE THEREOF

PROBLEM TO BE SOLVED: To provide a novel read-through inducer. SOLUTION: The present invention relates to a compound represented by the general formula (I) [each symbol in the formula is as described in the specification] or a pharmaceutically acceptable

Synthesis and evaluation of cyclohexane carboxylic acid head group containing isoxazole and thiazole analogs as DGAT1 inhibitors

Diacylglycerol acyltransferase 1 (DGAT1) is known to play an important catalytic role in the final step of triglyceride biosynthesis. High fat diet fed DGAT1 knockout mice were resistant to weight gain and exhibited increased insulin and leptin sensitivity thereby indicating a plausible role for DGAT1 inhibitors in the treatment of obesity. 4-Phenylpiperidine-1-carbonyl cyclohexanecarboxylic acid (compound 6, DGAT1 IC50 = 57 nM) has been lately reported as a potent DGAT1 inhibitor. In our search for newer scaffolds possessing potent DGAT1 activity we undertook a systematic diversification of compound 6 to identify a 4-(5-phenylthiazole-2-carboxamido)cyclohexanecarboxylic acid scaffold. Further linker optimization of this scaffold identified compound 9e (DGAT1 IC50 = 14.8 nM) as a potent DGAT1 inhibitor. Coupled with its in vitro potency, compound 9e also exhibited 112 percent plasma triglyceride reduction at a 3 mpk dose in an oral fat tolerance test (FTT) when studied in Swiss mice.

Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity.

Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors

Biphenyl carboxylic acids, exemplified by compound 5, are known potent inhibitors of diacylglycerol acyltransferase, DGAT1, an enzyme involved in the final committed step of triglyceride biosynthesis. We have synthesized and evaluated 2-phenylthiazole, 4-

HETEROCYCLIC COMPOUNDS AS DGAT1 INHIBITORS

The present invention relates to heterocyclic compounds of formula 1, in all their stereoisomeric and tautomeric forms; and their pharmaceutically acceptable salts, solvates, polymorphs, prodrugs, carboxylic acid isosteres and N-oxides. The invention also relates to processes for the manufacture of the heterocyclic compounds and to pharmaceutical compositions containing them. The said compounds and their pharmaceutical compositions are useful in the prevention and treatment of diseases or disorders mediated by diacylglycerol acyltransferase (DGAT), particularly DGAT1. The present invention further provides a method of treatment of such diseases or disorders by administering a therapeutically effective amount of said compounds or their pharmaceutical compositions, to a mammal in need thereof.

Synthesis and biological evaluation of isoxazole, oxazole, and oxadiazole containing heteroaryl analogs of biaryl ureas as DGAT1 inhibitors

Diacylglycerol acyltransferase, DGAT1, is a promising target enzyme for obesity due to its involvement in the committed step of triglyceride biosynthesis. Amino biphenyl carboxylic acids, exemplified by compound 4, are known potent inhibitors of hDGAT1. However the high cLogP and poor solubility of these biphenyl analogs might tend to limit their development. We have synthesized and evaluated compounds containing 3-phenylisoxazole, 5-phenyloxazole, and 3-phenyl-1,2,4-oxadiazole biaryl units for their hDGAT1 inhibition. Our aim in synthesizing such heterocyclic analogs was to improve the cLogP and solubility of these molecules while retaining hDGAT1 potency. Several compounds within the 3-phenylisoxazole series exhibited potent hDGAT1 inhibition when evaluated using an in vitro enzymatic assay. Certain promising compounds were studied for their potential to reduce triglyceride levels using an in vivo fat tolerance test in mice and were also evaluated for any possible improvement to their solubility. Compound 40a (IC50 = 64 nM) with an in vivo plasma triglyceride reduction of 90 percent, and a solubility of 0.43 mg/ml at pH 7.4 may serve as a new lead for developing newer anti-obesity agents.

Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds

Reaction of N-tert-butanesulfinyl α-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the co