27018-76-4

Basic information

• Product Name: 1-BENZYLINDOLE-3-CARBOXYLIC ACID
• Synonyms: 1-(phenylmethyl)-3-indolecarboxylic acid;1-(phenylmethyl)indole-3-carboxylic acid;INDOLE-3-CARBOXYLIC ACID, 1-BENZYL-;1H-Indole-3-carboxylicacid, 1-(phenylmethyl)-;RARECHEM AL BE 0270;1-benzyl-indole-3-carboxylicaci;1-BENZYLINDOLE-3-CARBOXYLIC ACID;1-BENZYL-1H-INDOLE-3-CARBOXYLIC ACID
• CAS NO: 27018-76-4
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• Product Categories: Building Blocks;C13 to C27;Chemical Synthesis;Heterocyclic Building Blocks;Indole;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 27018-76-4.mol

Chemical Properties

• Melting Point: 195-196 °C(Solv: ethanol (64-17-5))
• Boiling Point: 496.3 °C at 760 mmHg
• Flash Point: 254 °C
• Appearance: /Solid
• Density: 1.19 g/cm³
• Vapor Pressure: 1.14E-10mmHg at 25°C
• Storage Temp.: −20°C
• PKA: 3.98±0.10(Predicted)
• CAS DataBase Reference: 1-BENZYLINDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYLINDOLE-3-CARBOXYLIC ACID(27018-76-4)
• EPA Substance Registry System: 1-BENZYLINDOLE-3-CARBOXYLIC ACID(27018-76-4)

Safety Data

• WGK Germany: 3
• RTECS: NL5995800
• Hazardous Substances Data: 27018-76-4(Hazardous Substances Data)

Usage

Uses

1-Benzylindole-3-carboxylic acid is used as a reactant for the preparation of several types of compounds, each with its specific application in different industries. Here are the applications categorized by the industry and the application type:
Used in Pharmaceutical Industry:
1-Benzylindole-3-carboxylic acid is used as a reactant for the preparation of Indoleacetic acid analogs, which serve as differentiation-inducing and antiproliferative agents for human myeloblastoma cells. These analogs are crucial in cancer research and treatment, as they can potentially halt the uncontrolled growth of cancer cells.
1-Benzylindole-3-carboxylic acid is also used as a reactant for the synthesis of Indole-carboxamide derivatives, which act as inhibitors of lipid peroxidation and superoxide anion formation. These derivatives are significant in the development of antioxidants that can protect cells from oxidative stress and damage, which are common in various diseases, including cancer and neurodegenerative disorders.
In addition, 1-Benzylindole-3-carboxylic acid is used to prepare Indole carboxamides, which function as hyaluronidase inhibitors. These inhibitors are essential in the pharmaceutical industry for the treatment of conditions where the breakdown of hyaluronic acid is a concern, such as in some cancer metastasis and inflammatory diseases.
Furthermore, it is used to produce Fuconojirimycin derivatives, which are inhibitors of α-fucosidases. These derivatives have potential applications in the treatment of lysosomal storage diseases, such as fucosidosis, where the lack of a specific enzyme leads to the accumulation of unwanted substances in cells.
1-Benzylindole-3-carboxylic acid is also utilized in the preparation of Indole-2 and 3-carboxamides, which are selective cyclooxygenase-2 (COX-2) inhibitors. These inhibitors are vital in the development of anti-inflammatory drugs and pain relievers, as they target the specific enzyme responsible for inflammation and pain without affecting the COX-1 enzyme, which is essential for maintaining the protective lining of the stomach.
Lastly, 1-Benzylindole-3-carboxylic acid is used to synthesize Indole amides, which have antihistaminic properties. These compounds are employed in the development of antihistamine drugs, which are used to treat allergic reactions and symptoms such as itching, swelling, and sneezing.

InChI:InChI=1/C16H13NO2/c18-16(19)14-11-17(10-12-6-2-1-3-7-12)15-9-5-4-8-13(14)15/h1-9,11H,10H2,(H,18,19)/p-1

Upstream product

• 1217-89-6 1-benzylisatin 
• 105-39-5 chloroacetic acid ethyl ester 
• 10511-51-0 1-Benzylindole-3-carboxaldehyde 
• 141943-02-4 N-benzylindole-3-carboxylic acid benzyl ester 
• 155134-26-2 1-Benzyl-1H-indole-3-carboxylic acid methyl ester 
• 942-24-5 3-methoxycarbonylindole 
• 771-50-6 1H-indole-3-carboxylic acid 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 120-72-9 indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 3377-71-7 N-benzylindole 
• 124-38-9 carbon dioxide 

Downstream Products

• 313350-41-3 1-benzyl-1H-indole-3-carbonyl chloride 
• 942157-12-2 perfluorophenyl 1-benzyl-1H-indole-3-carboxylate 
• 942157-14-4 3-(1-benzyl-1H-indole-3-carbonyl)oxazolidin-2-one 
• 852059-34-8 1-benzyl-1H-indole-3-carboxylic acid pyridine-2-ylamide 
• 874889-01-7 C₂₉H₃₁N₃O₂ 
• 436151-81-4 1-benzyl-N-(8-(methylamino)-7,8-dioxooctyl)-1H-indole-3-carboxamide 
• 187945-09-1 (3S)-3-[(2S)-2-(1-benzylindol-3-ylcarbonylamino)-5-benzyloxycarbonylpentanoyl]oxy-4-(6-ethyl-2-naphthyl)butanamide 
• 852059-74-6 1-Benzyl-1H-indole-3-carboxylic acid pyrimidin-4-ylamide 

Relevant articles and documents

Pd(II)-Catalyzed asymmetric oxidative annulation of N-alkoxyheteroaryl amides and 1,3-dienes

The first Pd(II)-catalyzed asymmetric oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral heterocycles with high yields and enantioselectivities. A novel chiral pyridine-oxazoline bearing a methoxyl group at the C-5 position and a gem-dimethyl group on the oxazoline moiety was found to be crucial for conversion.

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[A] formation of Amyloid fibrils can be compounds, including therapeutic or prophylactic agent for neurodegenerative disease Amyloid fibrils formation inhibitor compound and of. (I) or its pharmaceutically acceptable compound represented by the formula [a] or a salt or solvate thereof includes the, Amyloid fibrils formation inhibitor. [R1 And R2 Each independently is H, an alkyl group, a cyano group or the like; R3 And R4 Each independently is H, or an alkyl group; R3 And R4 The, joint may form a ring; Ar1 And Ar2 The substituted or unsubstituted heteroaryl group are independently substituted/unsubstituted aryl groups /; X and Y are each independently a single bond, - (=O) - C etc., Z is O or CH2 ; N is an integer of 1 - 3][Drawing] no (by machine translation)

Synthesis and biological evaluation of novel indole derivatives containing sulfonamide scaffold as potential tubulin inhibitor

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Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.

Hydroxamic acids block replication of hepatitis c virus

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Construction of indoloquinolinones via Pd(II)-catalyzed tandem CC/CN bond formation: Application to the total synthesis of isocryptolepine

Construction of indoloquinolinone skeleton via Pd-catalyzed tandem CC/CN bond formation has been achieved in moderate to good yields. The method was applied toward the total synthesis of the bioactive natural product isocryptolepine in good overall yields.

Synthesis of 1-benzyl-3-[4-(aryl-1-piperazinyl) carbonyl]-1h-indoles. novel ligands with potential D4 dopaminergic activity

The synthesis of a series of functionalized 1-Benzyl-3-[4-Aryl-1- piperazingl]carbonyl-1H-Indoles 6(a-f), as a potential new class of bioactive ligands at D4 receptors is reported. The synthetic strategy took place through a five steps sequence

Effect of indole-3-acetic acid analogs on the differentiation of HL-60 cells

In continuing search for novel cell differentiation agents, a series of derivatives of indole-3-acetic acid and indole-3-carboxylic acid were prepared and tested against HL-60 cells for their differentiation and antiproliferation activities. Among them, N-ethyl-1-benzylindole-3-carboxamide (14) was the most potent, whereas N-methyl 1-benzylindole-3-acetamide (5) and N-methyl 1-benzylindole-3-carboxamide (13) synergistically potentiated with all-trans-retinoic acid to induce cell differentiation as well as antiproliferation. Our results indicate that these compounds are effective cell differentiation and antiproliferation agents in combination with retinoic acid.

Indol-3-yl-carbonyl-piperidin-benzoimidazol derivatives

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INDOL-3-YL-CARBONYL-SPIRO-PIPERIDINE DERIVATIVES AS V1A RECEPTOR ANTAGONISTS

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