18450-24-3

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYLINDOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as a reactant for the preparation of indole-based small molecules as anticancer agents. It plays a crucial role in the development of these agents by targeting the SIRT1 enzyme, which is involved in various cellular processes, including cell survival, metabolism, and aging. By inhibiting SIRT1, these indole-based small molecules can potentially lead to the suppression of cancer cell growth and the promotion of apoptosis, making them valuable in the fight against cancer.

InChI:InChI=1/C12H13NO2/c1-3-15-12(14)11-8-9-6-4-5-7-10(9)13(11)2/h4-8H,3H2,1-2H3

Upstream product

• 16136-58-6 N-methyl-1H-indole-2-carboxylic acid 
• 3770-50-1 2-carbethoxyindole 
• 74-83-9 methyl bromide 
• 13351-73-0 1-methyl-1H-benzo[d][1,2,3]triazole 
• 623-47-2 propynoic acid ethyl ester 
• 4792-54-5 ethyl pyruvate phenylhydrazone 
• 100-63-0 phenylhydrazine 
• 62-53-3 aniline 
• 126691-25-6 1-methyl-2-trimethylsilanyl-1H-indole 
• 1477-50-5 Indole-2-carboxylic acid 
• 64-17-5 ethanol 
• 128672-31-1 Ethyl Pyruvate 2-(2-Chlorophenyl)methylhydrazone 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1485-22-9 (1-methyl-1H-indol-2-yl)-methanol 
• 1446051-08-6 ethyl 3-[(methoxycarbonyl)(phenyl)methyl]-1-methyl-1H-indole-2-carboxylate 
• 1488427-09-3 N-{{5-fluoro-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indol-3-yl}methyl}-3-morpholinopropan-1-amine 
• 1488427-06-0 N-{{2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indol-3-yl}methyl}-2-morpholinoethan-1-amine 
• 1488427-08-2 N-{{2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indol-3-yl}methyl}-3-morpholinopropan-1-amine 
• 1488427-18-4 2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-3-[(4-methylpiperidin-1-yl)methyl]-1H-indole 
• 1488427-21-9 2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-3-(morpholinomethyl)-1H-indole 
• 1488427-22-0 3-[(2,6-dimethylmorpholino)methyl]-2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indole 
• 1488427-10-6 N-{{2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indol-3-yl}methyl}-2-(pyrrolidin-1-yl)ethan-1-amine 
• 1488427-23-1 2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-3-[(2-methylpiperidin-1-yl)methyl]-1H-indole 
• 1488427-24-2 2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-3-[(3-methylpiperidin-1-yl)methyl]-1H-indole 
• 1488427-16-2 N-{{2-[5-(isopropylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]-1-methyl-1H-indol-3-yl}methyl}(3-methoxyphenyl)methanamine 

Relevant academic research and scientific papers

Novel Indole-Quinazolinone Based Amides as Cytotoxic Agents

Indole-quinazolinone hybrids with active amides were synthesized, characterized, and assessed for their cytotoxicity. Two molecules displayed substantial activity in sulphorhodamine B assay method.

Asymmetric Transfer Hydrogenation of α-Substituted-β-Keto Carbonitriles via Dynamic Kinetic Resolution

A catalytic protocol for the enantio- and diastereoselective reduction of α-substituted-β-keto carbonitriles is described. The reaction involves a DKR-ATH process with the simultaneous construction of β-hydroxy carbonitrile scaffolds with two contiguous stereogenic centers. A wide range of α-substituted-β-keto carbonitriles were obtained in high yields (94%-98%) and excellent enantio- and diastereoselectivities (up to >99% ee, up to >99:1 dr). The origin of the diastereoselectivity was also rationalized by DFT calculations. Furthermore, this methodology offers rapid access to the pharmaceutical intermediates of Ipenoxazone and Tapentadol.

Design, synthesis, in-vitro evaluation and molecular docking studies of novel indole derivatives as inhibitors of SIRT1 and SIRT2

Sirtuins (SIRTs), class III HDAC (Histone deacetylase) family proteins, are associated with cancer, diabetes, and other age-related disorders. SIRT1 and SIRT2 are established therapeutic drug targets by regulating its function either by activators or inhi

Friedel-Crafts Chemistry. Part 53. Divergent and Diversity-Oriented Synthesis of Condensed Indole Scaffolds via Friedel-Crafts Ring Closure Approach

A series of indole-fused medium-sized N-heterocyclic systems 10a-h were prepared from laboratory-synthesized indole-based esters 9a-h via intramolecular Friedel-Crafts cyclizations induced by both trifluoromethanesulfonic acid and AlCl3/CH

Tandem Rh(II) and Chiral Squaramide Relay Catalysis: Enantioselective Synthesis of Dihydro-β-carbolines via Insertion to C-H Bond and Aza-Michael Reaction

An efficient tandem rhodium(II)/squaramide relay catalysis of readily accessible indole derivatives and N-sulfonyl-1,2,3-triazoles has been developed for the enantioselective synthesis of dihydro-β-carbolines in good yield and enantioselectivity. The developed reaction involves selective insertion of in situ generated azavinyl rhodium carbene onto the C3-H bond of indole derivatives and subsequent squaramide-catalyzed enantioselective intramolecular aza-Michael reaction. Furthermore, the potential of the strategy was demonstrated through the ready conversion to potent tetrahydro-β-carbolines and the tetracyclic alkaloid core structure.

Facile synthesis of indolelactones using Mn(III)-based oxidative substitution-cyclization reaction

Based on the oxidation of indole with Mn(OAc)3 in the presence of 1,1-diarylethenes affording 3-vinyl-substituted indoles, a similar oxidation using indole-2-carboxylic acids was evaluated in order to effectively introduce the substituent group to the C-3 position of the indolecarboxylic acids. The coupling reaction followed by oxidative cyclization smoothly proceeded at room temperature in an AcOH-HCO2H mixed solvent to give the desired indolelactones in high yields. The reaction details, the structure determination of the products and a brief reaction mechanism are described.

Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chemical space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogues of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions.

Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones

A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca

Piperazine analogs of naphthyridine-3-carboxamides and indole-2-carboxamides: Novel 5-HT3 receptor antagonists with antidepressant-like activity

Series of piperazine analogs of naphthyridine-3-carboxamides and indole-2-carboxamides were designed using a ligand-based approach with consideration of the pharmacophoric requirements for 5-HT3 receptor antagonists. The title carboxamides were synthesized using appropriate synthetic routes. Initially, the 5-HT3 receptor antagonistic activity of all the compounds was determined on isolated guinea pig ileum tissue against the 5-HT3 agonist, 2-methyl-5-hydroxytryptamine, which was denoted in the form of pA2 values. The structure-activity relationship regarding the influence of the aromatic part and basic moiety as features in the 5-HT3 pharmacophore was derived. Among all the compounds screened, the piperazine derivatives of indole-2-carboxamide 13i and naphthyridine-3-carboxamide 8h exhibited prominent 5-HT3 receptor antagonism with pA2 values of 7.5 and 7.3, respectively. Subsequent investigation of the antidepressant activities of selected compounds in the mouse forced swim test (FST) led to the identification of the piperazine analogs of indole-2-carboxamide 13i and naphthyridine-3-carboxamide 8h as the most promising compounds. Both 13i and 8h demonstrated significant reduction in the duration of immobility as compared to the control. Importantly, none of the tested compounds affected the baseline locomotion of mice at the tested dose levels.

Indole-3-carbinol and 1,3,4-oxadiazole hybrids: Synthesis and study of anti-proliferative and anti-microbial activity

In the present study, molecular hybrids of indole-3-carbinol and 1,3,4-oxadiazole-2-thiols have been designed and synthesized. The thiol analogues consisted of diversely substituted benzyl and alkyl groups with different electronic properties. The structures of all the newly synthesized scaffolds and target compounds were ascertained using 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. All the final compounds were screened in vitro for their anti-proliferative and anti-microbial activity. Three compounds showed excellent anti-proliferative activity with more than 70% cell growth inhibition against three cancer cell lines, HepG2 (human liver hepatocellular carcinoma), HeLa (human cervix carcinoma), and MCF-7 (human breast carcinoma). In the anti-microbial studies, compounds with electron-withdrawing fluoro or nitro substituent displayed appreciable activity similar to that of standard drugs. Also, the final compounds are non-toxic to non-cancerous Vero cell line.