16381-42-3

Basic information

• Product Name: ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate
• Synonyms: ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate
• CAS NO: 16381-42-3
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.2631
• Mol File: 16381-42-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate(16381-42-3)
• EPA Substance Registry System: ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate(16381-42-3)

Safety Data

• Hazardous Substances Data: 16381-42-3(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 607-97-6 ethyl 2-ethyl-3-oxobutanoate 
• 600-18-0 2-Oxobutyric acid 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 4792-58-9 ethyl 5-methoxy-1H-indole-2-carboxylate 
• 36820-78-7 3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester 
• 66552-11-2 ethyl 2-[(4-methoxyphenyl)amino]-3-oxobutanoate 
• 95239-03-5 tert-butyl 2-(4-ethoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate 

Downstream Products

• 16381-50-3 5-methoxy-3-methyl-1H-indole-2-carboxylic acid 
• 57291-56-2 5-ethoxy-3-methyl-indole-2-carboxylic acid 
• 78580-37-7 5-Methoxy-3-methyl-1-(2-nitro-phenyl)-1H-indole-2-carboxylic acid ethyl ester 
• 59908-57-5 5-methoxy-1,3-dimethyl-1H-indole-2-carboxylic acid 
• 2731-01-3 (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole 
• 168143-69-9 5-methoxy-3-methyl-1-(phenylsulfonyl)-1H-indole 
• 168143-73-5 1-benzenesulfonyl-3-bromomethyl-5-methoxyindole 
• 171820-27-2 1-tert-butyloxycarbonyl-N_b-benzyl-5-methoxytryptophan ethyl ester 
• 171018-94-3 (3S,6R)-6-(1-benzenesulfonyl-5-methoxy-3-indolyl)-methyl-3,6-dihydro-3-isopropyl-2,5-diethoxypyrazine 
• 600136-00-3 C₂₃H₂₄N₂O₂ 
• 600135-99-7 (6S,10S)-methyl-2-methoxy-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole-8-carboxylate 
• 409095-10-9 trans-N_b-benzyl-3-(ethoxycarbonyl)-6-methoxy-9-methyltetrahydro-β-carboline-1-propionic acid methyl ester 
• 600136-09-2 tert-butyl 3-(Hydroxymethyl)-5-methoxy-1H-indole-1-carboxylate 
• 600135-96-4 N_b-benzyl-5-methoxy-1-methyl-D-tryptophan ethyl ester 

Relevant articles and documents

Chemistry of pyrrolo[1,2-a]indole- and pyrido[1,2-a]indole-based quinone methides. Mechanistic explanations for differences in cytostatic/cytotoxic properties

(Chemical Equation Presented) In the present study we investigate pyrido[1,2-a]indole- and pyrrolo[1,2-a]indole-based quinones capable of forming quinone methide and vinyl quinone species upon reduction and leaving group elimination. Our goals were to det

PYRROLOBENZODIAZEPINE PRODRUGS AND ANTIBODY CONJUGATES THEREOF

The invention relates generally to pyrrolobenzodiazepine monomer and dimer prodrugs having a glutathione-activated disulfide prodrug moiety, a DT-diaphorase-activated quinone prodrug moiety or a reactive oxygen species-activated aryl boronic acid or aryl boronic ester prodrug moiety. The invention further relates to pyrrolobenzodiazepine prodrug dimer-antibody conjugates.

Development of potent dipeptide-type SARS-CoV 3CL protease inhibitors with novel P3 scaffolds: Design, synthesis, biological evaluation, and docking studies

We report the design and synthesis of a series of dipeptide-type inhibitors with novel P3 scaffolds that display potent inhibitory activity against SARS-CoV 3CLpro. A docking study involving binding between the dipeptidic lead compound 4 and 3CLpro suggested the modification of a structurally flexible P3 N-(3-methoxyphenyl)glycine with various rigid P3 moieties in 4. The modifications led to the identification of several potent derivatives, including 5c-k and 5n with the inhibitory activities (Ki or IC50) in the submicromolar to nanomolar range. Compound 5h, in particular, displayed the most potent inhibitory activity, with a Ki value of 0.006 μM. This potency was 65-fold higher than the potency of the lead compound 4 (Ki = 0.39 μM). In addition, the Ki value of 5h was in very good agreement with the binding affinity (16 nM) observed in isothermal titration calorimetry (ITC). A SAR study around the P3 group in the lead 4 led to the identification of a rigid indole-2-carbonyl unit as one of the best P3 moieties (5c). Further optimization showed that a methoxy substitution at the 4-position on the indole unit was highly favorable for enhancing the inhibitory potency.