25945-96-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(Benzyloxy)-4-nitroaniline is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs with diverse therapeutic applications.
Used in Dye Industry:
This chemical compound serves as a building block in the production of dyes, playing a crucial role in the creation of colorants for various applications, including textiles, plastics, and printing inks.
Used in Agrochemical Industry:
2-(Benzyloxy)-4-nitroaniline is utilized as an intermediate in the synthesis of pesticides and other agrochemicals, helping to develop effective solutions for crop protection and enhancement of agricultural productivity.

InChI:InChI=1/C13H12N2O3/c14-12-7-6-11(15(16)17)8-13(12)18-9-10-4-2-1-3-5-10/h1-8H,9,14H2

Upstream product

• 100-44-7 benzyl chloride 
• 121-88-0 5-Nitro-2-aminophenol 
• 100-39-0 benzyl bromide 
• 34288-19-2 N-(2-(benzyloxy)phenyl)acetamide 

Downstream Products

• 127028-17-5 2-(benzyloxy)-6-bromo-4-nitro-aniline 
• 757951-78-3 2-iodo-4-nitro-6-(phenylmethoxy)benzenamine 
• 112764-72-4 N-(2-Benzyloxy-4-nitro-phenyl)-benzamide 
• 25945-95-3 N-<2-(benzyloxy)-4-nitrophenyl>acetamide 
• 186355-81-7 (3R)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline 
• 174873-30-4 (3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline 
• 186355-79-3 (3R)-1-benzoyl-6-(benzoylamino)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-5-cyano-1,2,3,4-tetrahydroquinoline 
• 174873-27-9 (3S)-1-benzoyl-6-(benzoylamino)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-5-cyano-1,2,3,4-tetrahydroquinoline 
• 174873-28-0 (S)-6-Amino-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1,2,3,4-tetrahydro-quinoline-5-carbonitrile 
• 186355-87-3 (2R,8R)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4R)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline 

Relevant academic research and scientific papers

Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) alkylation subunit

The design, synthesis, and evaluation of methyl 1,2,8,8a-tetrahydrocyclopropa[c]imidazolo[4,5-e]indol-4-one-6-carboxylate (CImI) derivatives are detailed representing analogs of duocarmycin SA and yatakemycin containing an imidazole replacement for the fused pyrrole found in the DNA alkylation subunit.

Solid-Phase Synthesis of Duocarmycin Analogues and the Effect of C-Terminal Substitution on Biological Activity

The duocarmycins are potent antitumor agents with potential for use in the development of antibody-drug conjugates (ADCs) as well as being clinical candidates in their own right. In this article, we describe the synthesis of a duocarmycin monomer (DSA) th

Benzothiazole compounds and medical application

The invention discloses a benzothiazole compound and medical application thereof, particularly relates to a benzothiazole compound shown as a formula I and medical application thereof, and especiallyrelates to application of the benzothiazole compound serving as a USP7C-terminal structural domain regulating agent in medicines for preventing and treating myelodysplastic syndromes and malignant tumors. The benzothiazole compound shown in the formula I or the pharmaceutically acceptable salt or solvate of the benzothiazole compound has strong binding force with USP7C-terminal protein; and the protein level of DNMT1 in tumor cells can be reduced, so that the compound can be applied to the preparation of USP7 regulators, has a remarkable anti-tumor cell proliferation effect, and can be used for preparing medicines for preventing or treating myelodysplastic syndrome and malignant tumors.

SYNTHESIS OF DUOCARMYCIN ANALOGUES

A novel Fmoc protected duocarmycin subunit of formula (I) and utilisation as a reagent in solid phase protein synthesis methodology. Also provided is a novel method of solid phase peptide synthesis, and in particular a method for the production of novel i

Radiosynthesis of new carbon-11-labeled nimesulide analogs as potential PET SAER tracers for imaging of aromatase expression in breast cancer

Carbon-11-labeled nimesulide analogs, N-[11C]methyl-N-(2- benzyloxy-4-nitrophenyl)methanesulfonamide ([11C]4a), N-[ 11C]methyl-N-[2-(4'-methylbenzyloxy)-4-nitrophenyl] methanesulfonamide ([11C]4b), N-[11/s

Synthesis and biological evaluation of selective aromatase expression regulators in breast cancer cells

Aromatase converts androgens to estrogens and is a particularly attractive target in the treatment of estrogen receptor positive breast cancer. The enzyme is encoded by the CYP19 gene, which is expressed in a tissue-specific manner. Prostaglandin E2

SULFONANILIDE ANALOGS AS SELECTIVE AROMATASE MODULATORS

Compounds and methods suppressing aromatase activity expression in cancer cells. Provided are compounds are those of formula I: wherein R1 may be alkyl, cycloakyl, haloalkyl, aryl, substituted aryl, haloaryl, alkoxy, alkylaryl, and arylalkyl; R2 is H, alk

New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA

(Equation Presented) The sequential coupling and cyclization reactions between aryl halides and methyl propiolate were investigated. The electron-withdrawing groups on the aromatic ring are essential for producing the methyl indole-2-carboxylate derivativ

Arylsulfonamide ethers, and methods of use thereof

Novel arylsulfonamide ether compounds and pharmaceutical compositions thereof are described. The use of the novel arylsulfonamide ether compounds and pharmaceutical compositions thereof as inhibitors of interleukin-1β converting enzyme and other cysteine proteases in the ICE family is also decribed. In addition, methods of treating stroke, inflammatory diseases, septic shock, repurfusion injury, Alzheimer's disease, and shigellosis using a compound of the invention or a pharmaceutical composition thereof are described.

Total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A and their unnatural enantiomers: Assessment of chemical and biological properties

Full details of an enantioselective total synthesis of (+)-duocarmycin A (1) are described in which a solution to the control of the relative and absolute stereochemistry of the remote stereocenters is provided. Catalytic asymmetric dihydroxylation of 15 was employed to introduce the absolute stereochemistry required for the activated cyclopropane, and a diastereoselective Dieckmann-type condensation of 61 was employed to control the absolute stereochemistry of the C6 quaternary center. The complementary diastereoselectivity of a thermodynamic versus kinetic condensation of 61 permitted the divergent synthesis of (+)-duocarmycin A or epi-(+)-duocarmycin A from common intermediates. Final introduction of the reactive cyclopropane was accomplished by transannular spirocyclization of the mesylate 44 upon treatment with base or directly from the corresponding free alcohol itself, duocarmycin D1 (42), upon Mitsunobu activation. Notably, the asymmetric dihydroxylation of 15 employing (DHQD)2-PHAL/(DHQ)2-PHAL was found to proceed with a reverse enantioselectivity than predicted from established models. Employing this approach, the key partial structures (+)-N-BOC-DA (67) and (+)-6-epi-N-BOC-DA (71) and their unnatural enantiomers were also prepared, and a study of their acid-catalyzed solvolysis reactivity, regioselectivity (3:2), and stereochemistry is detailed. Notably, the solvolysis reaction regioselectivity is lower than the characteristic adenine N3 alkylation of duplex DNA, which proceeds with exclusive nucleophilic addition to the least substituted C8 cyclopropane carbon. This may be attributed to the significant destabilizing torsional strain and steric interactions characteristic of the S(N)2 reaction of a large nucleophile that accompany the abnormal addition of adenine when restricted to the minor groove bound orientation of the reactants.