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Chemical Structure| 1477-50-5 Chemical Structure| 1477-50-5
Chemical Structure| 1477-50-5

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CAS No.: 1477-50-5

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Indole-2-carboxylic acid is a strong inhibitor of lipid peroxidation.

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Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ～35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Kim, Ho Young ; Lee, Ji Youn ; Hsieh, Chia-Ju ; Taylor, Michelle ; Luedtke, Robert R ; Mach, Robert H

Abstract: Previous studies have confirmed that the binding of D3?receptor antagonists is competitively inhibited by endogenous dopamine despite excellent binding affinity for D3?receptors. This result urges the development of an alternative scaffold that is capable of competing with dopamine for binding to the D3?receptor. Herein, an SAR study was conducted on metoclopramide that incorporated a flexible scaffold for interaction with the secondary binding site of the D3?receptor. The alteration of benzamide substituents and secondary binding fragments with aryl carboxamides resulted in excellent D3?receptor affinities (Ki = 0.8–13.2 nM) with subtype selectivity to the D2?receptor ranging from 22- to 180-fold. The β-arrestin recruitment assay revealed that?21c?with 4-(pyridine-4-yl)benzamide can compete well against dopamine with the highest potency (IC50?= 1.3 nM). Computational studies demonstrated that the high potency of?21c?and its analogs was the result of interactions with the secondary binding site of the D3?receptor. These compounds also displayed minimal effects for other GPCRs except moderate affinity for 5-HT3?receptors and TSPO. The results of this study revealed that a new class of selective D3?receptor antagonists should be useful in behavioral pharmacology studies and as lead compounds for PET radiotracer development.

Keywords: D3 receptor antagonists ; metoclopramide ; bitopic ligand ; β-arrestin recruitment assay ; computational chemistry

Alternative Products

Product Details of Indole-2-carboxylic acid

CAS No. :1477-50-5
Formula : C9H7NO2
M.W : 161.16
SMILES Code : OC(=O)C1=CC2=CC=CC=C2N1
MDL No. :MFCD00005611
InChI Key :HCUARRIEZVDMPT-UHFFFAOYSA-N
Pubchem ID :72899

Safety of Indole-2-carboxylic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of Indole-2-carboxylic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1477-50-5 ]

[ 1477-50-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1477-50-5 ]
  • [ 65473-13-4 ]
  • 1<i>H</i>-indole-2-carboxylic acid methyl-naphthalen-1-ylmethyl-amide [ No CAS ]
  • 2
  • [ 5754-35-8 ]
  • [ 1477-50-5 ]
  • N-[2-(1,3-dioxolan-2-yl)ethyl]-1H-indole-2-carboxamide [ No CAS ]
  • 3
  • [ 1477-50-5 ]
  • [ 21109-25-1 ]
  • 5
  • [ 1477-50-5 ]
  • [ 101125-32-0 ]
  • [ 141306-08-3 ]
YieldReaction ConditionsOperation in experiment
In quinoline; diethyl ether; A mixture of the crude indole-2-carboxylic acid (55.0 g), Cu (2.0 g) and quinoline (1.0 l) was refluxed for 2.5 h, cooled and filtered. The filtrate was poured into water (800 ml) and extracted with diethyl ether (2*800 ml). The combined organic phases were succesively washed with 1N hydrochloric acid (4*1.0 l), washed with brine (1.0 l) and dried (Na2 SO4). Evaporation of the solvent in vacuo gave the title compound which was precipitated from diethyl ether. Yield: 43.6 g, mp 98-100 C. In a corresponding manner the following indole derivatives were prepared: 5-Chloro-3-(4-fluorophenyl)-1H-indole 1b, mp 81-83 C.
  • 6
  • [ 1477-50-5 ]
  • [ 2632-14-6 ]
  • [ 1002234-62-9 ]
  • 7
  • [ 36193-65-4 ]
  • [ 1477-50-5 ]
  • 8
  • [ 1477-50-5 ]
  • [ 20358-03-6 ]
  • N-(5-bromo-1,3-benzothiazol-2-yl)-1H-indole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20℃; General procedure: To a mixture of 225 ( 1 mmol) and HBTU or HATU (1 mmol) in NMP (12 mL) were added 224 (1 mmol) and DIPEA (2-3 mmol). The reaction mixture was stirred at rt for 12-24h, quenched with H20 and extracted with EtOAc. The organic layer was washed with H20, brine, dried over anhydrous Na2S04 and concentrated. The crude product was purified by automated flash chromatography to give the desired product.
13% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20℃; for 24h; To a mixture of 1H-indole-2-carboxylic acid (84 mg, 0.52 mmol, 1.0 eq.) and HBTU (237 mg, 0.62 mmol, 1.0 eq.) in NMP (6 mL) were added<strong>[20358-03-6]5-bromo-1,3-benzothiazol-2-amine</strong> (120 mg, 0.52 mmol, 1.0 eq.) andDIPEA (180 muL, 1.04 mmol, 2.0 eq.).The reaction mixture was stirred at room temperature during 24 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid and 1M sodium hydroxide aqueous solutions, and then was dried over Na2SO4. The solvent was evaporated under reduced pressure and the residue purified by silica gel flash-column chromatography (eluent: heptane/EtOAc, 90/10 to 70/30) to afford26cas a white solid (25 mg, 13 percent).1H NMR(DMSO-d6, 500 MHz):d(ppm): 7.11 (1H, t, J6-5=J6-4=7.6Hz, H6), 7.29 (1H, t, J5-4=J5-6=7.6Hz, H5), 7.50 (1H, d, J4-5= 7.6Hz, H4), 7.51 (1H, dd, J6?-7?= 8.5Hz, J6?-4?= 1.8Hz, H6?), 7.71 (1H, d, J7-6= 7.6Hz, H7), 7.77 (1H, s, H3), 8.00 (1H, bs, H4?), 8.02 (1H, d, J7?-6?= 8.5Hz, H7?), 12.03 (1H, s, indolic H), 13.11 (1H, s, amide H).13C NMR (DMSO-d6, 150 MHz):d(ppm): 107.3 (C3), 113.1 (C4), 119.4 (C5?), 120.8 (C6), 122.9 (C7), 123.2 (C4?), 124.1 (C7?), 125.4 (C5), 126.7 (C6?), 127.4 (C3a), 129.2 (C2), 131.4 (C7a?), 138.1 (C7a), 150.7 (C3a?), 160.4 (C8), 160.6 (C2?).HRMS calcd for C16H1179BrN3OS: m/z = 371.9806, found: 371.9839.
  • 9
  • [ 1477-50-5 ]
  • [ 59878-57-8 ]
  • 2-[(4-cyclopropylcarbonylpiperazine-1-yl)carbonyl]-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% General procedure: A solution of 1,1?-carbonyldiimidazole (CDI) in THF (3 ml, 3.7 mmol) was added to indole-2-carboxylic acid (3.1 mmol) in THF (5 ml) at room temperature and stirred for 1 hunder N2. Then, the reaction mixture was cooled to 0d fC andN-substituted piperazine derivatives (3.7 mmol) in THF (3ml) were added and stirred for further 17-18 h at roomtemperature. Basic workup (CHCl3, sat. NaHCO3) wasapplied, evaporated under vacuo and recrystallization fromethyl acetate:n-hexane provided the desired compounds (1,4-15, Scheme 1).
  • 10
  • [ 1477-50-5 ]
  • [ 30465-68-0 ]
  • C19H15N3O2 [ No CAS ]
  • 11
  • [ 1477-50-5 ]
  • [ 36887-98-6 ]
  • C18H17N3O [ No CAS ]
 

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