15992-10-6

Usage

Uses

Used in Medicinal Chemistry:
2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide is used as a chemical intermediate for the development of new pharmaceuticals, leveraging its complex molecular structure to target specific biological pathways and create novel therapeutic agents.
Used in Pharmaceuticals:
In the pharmaceutical industry, 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide is used as a potential active ingredient, given its possible biological activities that could be harnessed for treating various medical conditions.
Used in Agrochemicals:
2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide is used as a component in agrochemicals, potentially for its ability to influence plant or pest biology, contributing to crop protection or enhancement strategies.
Used in Synthesis of Complex Molecules:
As a building block, 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide is used in the synthesis of more complex organic molecules, which could lead to the creation of advanced materials or new pharmaceutical entities.
The specific applications and effectiveness of 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide in these areas would need to be confirmed through rigorous scientific research and validation processes.

InChI:InChI=1/C12H14N2O2/c1-7-9(6-12(13)15)10-5-8(16-2)3-4-11(10)14-7/h3-5,14H,6H2,1-2H3,(H2,13,15)

Upstream product

• 2882-15-7 5-Methoxy-2-methylindole-3-acetic acid 
• 57-13-6 urea 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 6264-33-1 Indomethacin amide 
• 69181-73-3 C₂₂H₂₀ClNO₆ 

Downstream Products

• 1568-30-5 2-(1-benzoyl-5-methoxy-2-methyl-indol-3-yl)-acetamide 
• 97077-43-5 3-(amidomethyl)-2-methyl-1-(phenylmethyl)-5-methoxyindole 
• 871483-20-4 4-chloro-N-[2-(5-methoxy-2-methyl-1H-indol-3-yl)-ethyl]-benzamide 
• 871483-21-5 N-[2-(5-methoxy-2-methyl-1H-indol-3-yl)-ethyl]-3-phenyl-propionamide 
• 819079-77-1 N-{2-[1-(4-bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester 
• 68935-42-2 N-[2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]acetamide 
• 164084-24-6 3-(amidomethyl)-2-methyl-1-(phenylmethyl)-5-hydroxyindole 
• 1036648-56-2 5-methoxy-2-methyl-1H-1-(o-pentoxy)benzylindole-3-acetamide 
• 1477811-16-7 2-(1-(2-((5-chloropentyl)oxy)benzyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetamide 
• 1477811-29-2 C₂₈H₂₈N₂O₅ 
• 1477811-33-8 C₂₉H₃₀N₂O₅ 

Relevant academic research and scientific papers

Novel dual inhibitors of secretory phospholipase A2 and sphingomyelin synthase: Design, synthesis and evaluation

Atherosclerosis is a fatal disease for decades, which was thought to be the basis onset of many other cardiovascular diseases. Its pathogenesis is complex, mainly for the chronic vascular inflammation symptoms caused by abnormal lipid metabolism. Inflammation has been recognized as the pivotal role during every step of atherosclerosis. In view of the complication of its pathogenic process, the multi-target medication sometimes is more effective, less side effect and could reduce tolerance which should be another reasonable strategy for anti-atherosclerosis. Sphingomyelin synthase (SMS) is a potential therapeutic target for atherosclerosis treatment, while secretory phospholipase A2 (sPLA2) have been studied as a target of atherosclerosis treatment which plays an important role in the genesis and development of its progress of atherosclerosis. Based on the complex pathogenesis of atherosclerosis, we focused on two key enzymes in this process-SMS and sPLA2. We combined with the existing QSAR of the inhibitors of SMS and sPLA2 and rational multi-target drug design ideas, three series of dual inhibitors of sPLA2 and SMS were designed by linking or fusing SMS inhibitor fragment Ly18 (N-pyridine-3-amide moiety) with sPLA2 inhibitor fragment (indole- 3-acetamide structure) by 3-6 carbon chain as novel dual-functional inhibitors series 1-3. Series 2 and 3 reserved benzyl in sPLA2 or SMS pharmacophore respectively, while series 1 was de-benzyl in order to decrease the molecular weight. Eleven target molecules were synthesized and bio-assayed in vitro. The results showed compounds 3a-3d provided inhibitory activities against SMS2 and 2a-2d exhibited the sPLA2 inhibition activities. The compound 3c showed equivalent activities of both SMS and sPLA2 which would be a potential leading compound of dual inhibitor against atherosclerosis.

Design, synthesis, and biological evaluation of novel dual inhibitors of secretory phospholipase A2 and sphingomyelin synthase

A novel series of eight SMS and sPLA2 dual inhibitors containing indole and α-amino cyanide fragments of different length and substitution position was synthesized and evaluated by three different in vitro assays. Biological evaluation showed that all compounds provided inhibitory effects against SMS (about 50% inhibition at 100 μmol/L) and sPLA2 (14-32 μmol/L). All the compounds had the SMS activity better than the positive control compound D609 in SMS2 homogenate, with compounds 5b and 5e ideal for liver homogenate and SMS2 high expression cell homogenate, respectively. The secretory phospholipase A2 (sPLA2) and sphingomyelin (SMS) are the key enzymes to atherosclerosis. In this paper, we combined the single sPLA2 and SMS inhibitors with a carbon chain to get a series of dual inhibitors. The biological evaluation showed these compounds had the moderate inhibition against both enzymes. Copyright

Indole-5-phenylcarbamate derivatives as human non-pancreatic secretory phospholipase A2 inhibitor

The synthesis of the human non-pancreatic secretory phospholipase A2 inhibitor (IC50 = 1.81 ± 0.59 μM) is reported.

Indolyl esters and amides related to indomethacin are selective COX-2 inhibitors

Previous studies from our laboratory have revealed that esterification/amidation of the carboxylic acid moiety in the nonsteroidal anti-inflammatory drug, indomethacin, generates potent and selective COX-2 inhibitors. In the present study, a series of reverse ester/amide derivatives were synthesized and evaluated as selective COX-2 inhibitors. Most of the reverse esters/amides displayed time-dependent COX-2 inhibition with IC 50 values in the low nanomolar range. Replacement of the 4-chlorobenzoyl group on the indole nitrogen with a 4-bromobenzyl moiety resulted in compounds that retained selective COX-2 inhibitory potency. In addition to inhibiting COX-2 activity in vitro, the reverse esters/amides also inhibited COX-2 activity in the mouse macrophage-like cell line, RAW264.7. Overall, this strategy broadens the scope of our previous methodology of neutralizing the carboxylic acid group in NSAIDs as a means of generating COX-2-selective inhibitors and is potentially applicable to other NSAIDs.

COX-2-targeted imaging agents

The presently disclosed subject matter provides a method for synthesizing a radiological imaging agent by reacting a COX-2-selective ligand with a compound comprising a detectable group, wherein the COX-2-selective ligand is a derivative of a non-steroidal anti-inflammatory drug (NSAID) comprising an ester moiety or a secondary amide moiety. Also provided are compositions that are synthesized using the method, as well as methods of using the compositions of the presently disclosed subject matter.

Esters derived from indolealkanols and novel amides derived from indolealkylamides that are selective COX-2 inhibitors

A compound of the formula where: n, and X are as defined in the specification, and the compound possesses selectivity for inhibition of cyclooxygenase-2.

Indole inhibitors of human nonpancreatic secretory phospholipase A2. 1. Indole-3-acetamides

Phospholipases (PLAs) produce rate-limiting precursors in the biosynthesis of various types of biologically active lipids involved in inflammatory processes. Increased levels of human nonpancreatic secretory phospholipase A2 (hnps-PLA2) have been detected in several pathological conditions. An inhibitor of this enzyme could have therapeutic utility. A broad screening program was carried out to identify chemical structures which could inhibit hnps-PLA2. One of the lead compounds generated by the screening program was 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid (13a). We describe the syntheses, structure-activity relationships, and pharmacological activities of a series of indole-3-acetamides and related compounds derived from this lead. This SAR was undertaken with the aid of X- ray crystal structures of complexes between the inhibitors and hnps-PLA2 which were of great value in directing the SAR.