83304-13-6

Usage

Uses

Used in Pharmaceutical Industry:
3-NITROPHENYLETHYLAMINE is used as a TRPM8 inhibitor for treating diseases or conditions caused by hyperexcitability of afferent nerves. TRPM8 is a calcium-permeable ion channel that is activated by cold temperatures and can be involved in pain sensation. By inhibiting TRPM8, 3-NITROPHENYLETHYLAMINE can help alleviate pain and discomfort associated with these conditions.
Used in Chemical Synthesis:
3-NITROPHENYLETHYLAMINE can also be used as a chemical intermediate in the synthesis of various compounds. Its reactivity and functional groups make it a useful building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
In addition to its practical applications, 3-NITROPHENYLETHYLAMINE is also used in research and development settings. It can be employed as a tool compound to study the structure-activity relationships of TRPM8 inhibitors and to gain insights into the mechanisms of action of these compounds. Furthermore, it can be used to develop new assays and screening methods for identifying novel TRPM8 inhibitors with improved potency and selectivity.

InChI:InChI=1/C8H10N2O2/c1-2-9-7-4-3-5-8(6-7)10(11)12/h3-6,9H,2H2,1H3

Upstream product

• 7697-37-2 nitric acid 
• 64-04-0 phenethylamine 
• 134306-94-8 3-(3-nitrophenyl)propanamide 
• 621-50-1 (3-nitrophenyl)acetonitrile 
• 223741-86-4 1-(2-azidoethyl)-3-nitrobenzene 
• 75-09-2 dichloromethane 
• 603-35-0 triphenylphosphine 
• 1403029-71-9 2-3-nitrophenylethylcarbamic acid methyl ester 
• 555-68-0 m-Nitrocinnamic Acid 
• 22888-56-8 3-nitrophenylalanine 
• 882-26-8 (E)-1-nitro-3-(2-nitrovinyl)benzene 
• 619-23-8 3-Nitrobenzyl chloride 
• 1664-57-9 3-(3-nitrophenyl)propanoic acid 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 76935-75-6 2-(3-aminophenyl)ethylamine 
• 121-92-6 3-nitrobenzoic acid 
• 180079-93-0 N-(3-nitrophenylmethyl)methylcarbamic acid t-butyl ester 
• 135365-07-0 N-acetyl-N-(3-nitrophenethyl)amine 
• 1185466-27-6 C₃₂H₃₉N₃O₅Si 
• 1185463-88-0 N-(2,6-dichlorobenzyl)-N'-[3-(2-{[(2R,S)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}ethyl)phenyl]urea 
• 1185463-82-4 N-(diphenylmethyl)-N'-[3-(2-{[(2R,S)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}ethyl)phenyl]urea 
• 1185463-90-4 N-biphenyl-2-yl-N'-[3-(2-{[(2RS)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}ethyl)phenyl]urea 
• 1185464-03-2 N-[3-(2-{[(2R,S)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]-amino}ethyl)phenyl]-N'-(3-phenoxyphenyl)urea 
• 1185464-34-9 N-(4-tert-butylbenzyl)-N'-[3-(2-{[(2R,S)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydro-quinolin-5-yl)ethyl]amino}ethyl)phenyl]urea 
• 1185463-83-5 N-[3-(2-{[(2R,S)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]-amino}ethyl)phenyl]-N'-phenylurea 
• 1185465-25-1 tert-butyl [2-(3-isocyanatophenyl)ethyl]carbamate 
• 1185465-48-8 tert-butyl (2-{3-[(anilinocarbonyl)amino]phenyl}ethyl)carbamate 
• 1185465-18-2 tert-butyl [2-(3-{[(benzylamino)carbonyl]amino}phenyl)ethyl]-carbamate 

Relevant academic research and scientific papers

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines

The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Heterocyclic compounds as Wee1 inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

Activation of electrophilicity of stable Y-delocalized carbamate cations in intramolecular aromatic substitution reaction: Evidence for formation of diprotonated carbamates leading to generation of isocyanates

Although cations with three heteroatoms, such as monoprotonated guanidine and urea, are stabilized by Y-shaped conjugation and such Y-conjugated cations are sufficiently basic to be further protonated (or protosolvated) to dications in strongly acid media, only O-monoprotonated species have been detected in the case of carbamates even in magic acid. We found that the trifluoromethanesulfonic acid-catalyzed cyclization of arylethylcarbamates proceeds to afford dihydroisoquinolones in high yield. In strong acids, methyl carbamates are fully O-monoprotonated, and these monocations do not undergo cyclization even under heating. But, as the acidity of the reaction medium is further increased, the cyclization reaction of methyl phenethylcarbamates starts to proceed as a first-order reaction, with a linear relationship between rate and acidity. The sign and magnitude of the entropy of activation ΔS ? were found to be similar to those of other AAc1 reactions. These results strongly support the idea that further protonation of the O-protonated carbamates is involved in the cyclization, but the concentration of the dications is very low and suggests that the rate-determining step is dissociation of methanol from the diprotonated carbamate to generate protonated isocyanate, which reacts with the aromatic ring. Therefore, O-protonated carbamates are weak bases in sharp contrast to other Y-shaped monocations.

Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids

A one-pot synthesis of tetrahydroisoquinoline alkaloids in a phosphate buffer has been achieved, and a reaction mechanism proposed. The utilisation of mild reaction conditions readily afforded a range of isoquinolines, including norcoclaurine.

Discovery of substituted phenyl urea derivatives as novel long-acting β2-adrenoreceptor agonists

The synthesis of diverse functionalized ureas in a semi-parallel fashion is described, as well as their β1/β2-adrenergic activities and the corresponding structure-activity relationship (SAR). We have focused on lipophilicity and duration of action, and we have discovered a strong correlation in this series of molecules. A quantitative structure-activity relationship (QSAR) analysis will be presented that quantifies this relationship.

BICYCLOANILINE DERIVATIVE

The invention relates to a compound of a general formula (I): wherein A1 and A2 each mean a nitrogen atom or an optionally-substituted methine group; Ring B means a 5-membered to 7-membered aliphatic ring, or a spiro or bicyclo ring formed from the aliphatic ring and any other 3-membered to 7-membered aliphatic ring; R1 means a hydrogen atom, or an optionally-substituted C1-C6 alkyl group, or an optionally-substituted aryl, aralkyl or heteroaryl group; R2 means an optionally-substituted aryl, aralkyl or heteroaryl group; and X means a group of =NH or =O, etc. Based on its excellent Wee1 kinase-inhibitory effect, the compound of the invention has cell growth-inhibitory effect and has an additive/synergistic effect with any other anticancer agent, and is therefore useful in the field of medicine.

Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor

The present invention provides a compound of formula (I): wherein: R1 is a group selected from -CH2OH,-NHCOH and R2 is a hydrogen atom; or R1 together with R2 form the group -NHC(O)CH=CH-, wherein the nitrogen atom is bound to the carbon atom in the phenyl ring holding R1 and the carbon atom is bound to the carbon atom in the phenyl ring holding R2, R3a and R3b are independently selected from the group consisting of hydrogen atoms and C1-4 alkyl groups n is an integer selected from 0 to 6, R4 is selected from the group consisting of an optionally substituted monocyclic or polycyclic C3-10 cycloalkyl group, an optionally substituted monocyclic C5-10 aryl group and, a methyl group which is substituted with one or more substituents selected from C5-10 aryl and C5-10 aryloxy groups, wherein the monocyclic or polycyclic C3-10 cycloalkyl and the monocyclic C5-10 aryl groups independently are optionally substituted with one or more substituents selected from halogen atoms, C1-4 alkyl, C1-4 alkoxy, C5-10 aryl and C5-10 aryloxy groups, or a pharmaceutically-acceptable salt or solvate or stereoisomer thereof.

AMINOETHYLAROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR

The present invention relates to aromatic compounds of the formula (I) wherein Ar is phenyl or an aromatic 5-or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; E is CR6R7 or NR3;R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated Cl-C4--alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C 4-cycloalkylmethyl, fluorinated C3-C4--alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1--C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C 3-C4-cycloalkylmethyl, fluorinated C3--C 4-alkenyl, or R1a and R2 together are (CH 2)n with n being 2, 3 or 4, or R1a and R 2a together are (CH2)n with n being 2, 3 or 4; R2 and R2a are independently of each other H, C1-C4-alkyl or fluorinated C1-C 4-alkyl or R2a and R2 together are (CH 2)m with m being 1, 2, 3, 4 or 5; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, fluorine, C1-C4-alkyl and fluorinated C1-C4-alkyl or together form a moiety (CH2)p with p being 2, 3, 4 or 5; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

Integrin expression inhibitors

The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them. In the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, —CH═CH— or —(CR4bR5b)mb— (wherein R4b and R5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and mb means an integer of 1 or 2); R1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or —CO—NH—; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.