19500-02-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxy-2-methylaniline is used as a chemical intermediate for the synthesis of indoles and indazoles, which possess potential neurochemical activity. These compounds can be further utilized in the development of drugs targeting the central nervous system.
Used in Antiviral Agents:
3-Methoxy-2-methylaniline is also used as a chemical intermediate in the preparation of quinoline-based antiviral agents. These agents can be effective in treating various viral infections by inhibiting essential viral enzymes or disrupting the viral replication process.
Chemical Properties:
3-Methoxy-2-methylaniline is a brown oil, indicating its non-crystalline and viscous nature. This physical state can influence its solubility, reactivity, and ease of handling in chemical reactions and industrial processes.

InChI:InChI=1/C8H11NO/c1-6-7(9)4-3-5-8(6)10-2/h3-5H,9H2,1-2H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 5460-31-1 3-nitro-o-cresol 
• 164082-77-3 tert-butyl (3-methoxy-2-methylphenyl)carbamate 
• 1045866-39-4 3-methoxy-2-methylaniline trifluoroacetate 
• 4837-88-1 6-methoxy-2-nitrotoluene 

Downstream Products

• 6971-52-4 3-methoxy-2-methylphenol 
• 50868-74-1 acetic acid-(3-methoxy-2-methyl-anilide) 
• 80563-85-5 6-methoxy-toluene-2-sulfonic acid amide 
• 156267-25-3 Benzotriazol-1-ylmethyl-(3-methoxy-2-methyl-phenyl)-amine 
• 19646-49-2 Brenztraubensaeure-aethylester-<3-methoxy-2-methyl-phenylhydrazon> 
• 17897-50-6 4-methoxy-2-methylindole 
• 164083-26-5 1-(2-(tert-butoxycarbonylamino)-6-methoxyphenyl)-2-propanone 
• 164082-78-4 1-[2-(tert-butoxycarbonylamino)-6-methoxyphenyl]-2-butanone 
• 172733-40-3 1-[2-(tert-butoxycarbonylamino)-6-methoxyphenyl]-2-pentanone 
• 185063-88-1 [2-(2-Cyclopropyl-2-oxo-ethyl)-3-methoxy-phenyl]-carbamic acid tert-butyl ester 
• 164082-81-9 2-ethyl-4-methoxy-alpha-oxo-1-(phenylmethyl)-1H-indole-3-acetamide 
• 1027660-59-8 (1-Benzyl-2-ethyl-4-methoxy-1H-indol-3-yl)-oxo-acetyl chloride 
• 164082-82-0 2-ethyl-4-methoxy-alpha-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide 
• 164083-29-8 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors

Since Hsp90 modulates all six hallmarks of cancer simultaneously, it has become an attractive target for the development of cancer chemotherapeutics. In an effort to develop more efficacious compounds for Hsp90 inhibition, novobiocin analogues were prepared by replacing the central coumarin core with naphthalene, quinolinone, and quinoline surrogates. These modifications allowed for modification of the 2-position, which was previously unexplored. Biological evaluation of these compounds suggests a hydrophobic pocket about the 2-position of novobiocin. Anti-proliferative activities of these analogues against multiple cancer cell lines identified 2-alkoxyquinoline derivatives to exhibit improved activity.

IMIDAZOLIDINEDIONE DERIVATIVES

The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.

Toward biophysical probes for the 5-HT3 receptor: Structure-activity relationship study of granisetron derivatives

This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT3A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one such position and specifically bound to 5-HT3A receptors in mammalian cells.

Protective Agent for Retinal Neuronal Cell Comprising Indazole Derivative as Active Ingredient

As a result of intensive studies for the purpose of finding a new medicinal use of an indazole derivative, it was found that an indazole derivative inhibits glutamate-induced retinal neuronal cell death in rat fetal retinal neuronal cells, in other words, the indazole derivative acts directly on the retinal neuronal cells and exhibits an effect of protecting retinal neuronal cells. Accordingly, the indazole derivative is useful for the prevention or treatment of an eye disease associated with retinal neuronal cell damage or retinal damage.

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

SAR analysis performed with a limited set of cyclopentane-containing macrocycles led to the identification of N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]- 13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamid e (TMC435350, 32c) as a potent inhibitor of HCV NS3/4A protease (Ki = 0.36 nM) and viral replication (replicon EC50 = 7.8 nM). TMC435350 also displayed low in vitro clearance and high permeability, which were confirmed by in vivo pharmacokinetic studies. TMC435350 is currently being evaluated in the clinics.

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Starting from the previously reported HCV NS3/4A protease inhibitor BILN 2061 (1), we have used a fast-follower approach to identify a novel series of HCV NS3/4A protease inhibitors in which (i) the P3 amino moiety and its capping group have been truncated, (ii) a sulfonamide is introduced in the P1 cyclopropyl amino acid, (iii) the position 8 of the quinoline is substituted with a methyl or halo group, and (iv) the ring size of the macrocycle has been reduced to 14 atoms. SAR analysis performed with a limited set of compounds led to the identification of N-{17-[8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo [13.3.0.0 [Bartenschlager, R.; Lohmann, V. J. Gen. Virol. 2000, 81, 1631; Vincent Soriano, Antonio Madejon, Eugenia Vispo, Pablo Labarga, Javier Garcia-Samaniego, Luz Martin-Carbonero, Julie Sheldon, Marcelle Bottecchia, Paula Tuma, Pablo Barreiro Expert Opin. Emerg. Drugs, 2008, 13, 1-19]]octadec-7-ene-4-carbonyl}(1-methylcyclopropyl)(1-methylcyclopropyl)sulfonamide 19l an extremely potent (Ki = 0.20 nM, EC50 = 3.7 nM), selective, and orally bioavailable dipeptide NS3/4A protease inhibitor, which has features attractive for further preclinical development.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

POLYMORPHIC FORMS OF A MACROCYCLIC INHIBITOR OF HCV

Provided are crystalline forms of the compound of formula (I), which is a macrocyclic inhibitor of HCV, processes for the preparation thereof, and pharmaceutical compositions comprising these crystalline forms.

Structure-activity relationships in the acronycine and benzo[b]acronycine series: Role of the pyran ring

In order to explore the structure-activity relationships in the acronycine series, simplified analogues of cis-1,2-diacetoxy-1,2-dihydroacronycine and cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1, under clinical trials) lacking the fused pyran ring, but possessing an acetoxymethyl leaving group at position 4 were prepared. These new analogues only displayed marginal antiproliferative activity compared to the parent compounds. The presence of the angularly fused dimethylpyran ring appears as an indispensable structural requirement to observe significant cytotoxic activity in this series.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.