94918-24-8

Upstream product

• 100-39-0 benzyl bromide 
• 17536-38-8 ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 123-76-2 levulinic acid 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 

Downstream Products

• 163735-06-6 2-(1-benzyl-5-hydroxy-2-methyl-1H-indol-3-yl)acetic acid 
• 97077-43-5 3-(amidomethyl)-2-methyl-1-(phenylmethyl)-5-methoxyindole 
• 163734-57-4 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide 

Relevant academic research and scientific papers

Indole Based Weapons to Fight Antibiotic Resistance: A Structure-Activity Relationship Study

Antibiotic resistance represents a worldwide concern, especially regarding the outbreak of methicillin-resistant Staphylococcus aureus, a common cause for serious skin and soft tissues infections. A major contributor to Staphylococcus aureus antibiotic resistance is the NorA efflux pump, which is able to extrude selected antibacterial drugs and biocides from the membrane, lowering their effective concentrations. Thus, the inhibition of NorA represents a promising and challenging strategy that would allow recycling of substrate antimicrobial agents. Among NorA inhibitors, the indole scaffold proved particularly effective and suitable for further optimization. In this study, some unexplored modifications on the indole scaffold are proposed. In particular, for the first time, substitutions at the C5 and N1 positions have been designed to give 48 compounds, which were synthesized and tested against norA-overexpressing S. aureus. Among them, 4 compounds have NorA IC50 values lower than 5.0 μM proving to be good efflux pump inhibitor (EPI) candidates. In addition, preliminary data on their ADME (absorption, distribution, metabolism, and excretion) profile is reported.

1H-INDOLE-3-ACETAMIDE SPLA2 INHIBITORS

A class of novel 1-indole-3-acetamides represented by the formula; is disclosed together with the use of such indole compounds for inhibiting sPLA2 mediated release of fatty acids.

1H-INDOLE-3-ACETIC ACID HYDRAZIDE SPLA2 INHIBITORS

A class of novel 1H-indole-3-acetic acid hydrazides is disclosed together with the use of such indole compounds for inhibiting sPLA2 mediated release of fatty acids (e.g., arachidonic acid) for treatment of conditions such as septic shock

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.