Cas no 133738-76-8 (7-Acetyl-1H-indole-2-carboxylic acid)

7-Acetyl-1H-indole-2-carboxylic acid is a versatile indole derivative with significant utility in organic synthesis and pharmaceutical research. Its structural features, including the acetyl and carboxylic acid functional groups, make it a valuable intermediate for constructing complex heterocyclic compounds. The compound exhibits high reactivity, enabling efficient derivatization for applications in medicinal chemistry, such as the development of bioactive molecules. Its well-defined purity and stability ensure consistent performance in reactions, while its compatibility with various synthetic methodologies enhances its utility in multi-step synthesis. Researchers value this compound for its role in producing tailored indole-based scaffolds, which are critical in drug discovery and material science applications.
7-Acetyl-1H-indole-2-carboxylic acid structure
133738-76-8 structure
Product Name:7-Acetyl-1H-indole-2-carboxylic acid
CAS No:133738-76-8
MF:C11H9NO3
MW:203.194062948227
CID:899760
PubChem ID:23510296
Update Time:2025-11-06

7-Acetyl-1H-indole-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 7-Acetyl-1H-indole-2-carboxylic acid
    • 7-acetyl-2-indole carboxylic acid
    • Inchi: 1S/C11H9NO3/c1-6(13)8-4-2-3-7-5-9(11(14)15)12-10(7)8/h2-5,12H,1H3,(H,14,15)
    • InChI Key: HKCBXLRQUQSXEB-UHFFFAOYSA-N
    • SMILES: O=C(C)C1=CC=CC2C=C(C(=O)O)NC=21

Computed Properties

  • Exact Mass: 203.05800
  • Monoisotopic Mass: 203.058243149g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 290
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 70.2?2

Experimental Properties

  • PSA: 70.16000
  • LogP: 2.06870

7-Acetyl-1H-indole-2-carboxylic acid Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

7-Acetyl-1H-indole-2-carboxylic acid Pricemore >>

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Additional information on 7-Acetyl-1H-indole-2-carboxylic acid

7-Acetyl-1H-indole-2-carboxylic acid (CAS No. 133738-76-8): A Key Intermediate in Modern Pharmaceutical Research

7-Acetyl-1H-indole-2-carboxylic acid, with the chemical identifier CAS No. 133738-76-8, is a significant compound in the realm of pharmaceutical chemistry, serving as a versatile intermediate in the synthesis of various bioactive molecules. Its unique structural framework, featuring both an acetyl group and a carboxylic acid moiety attached to an indole core, makes it a valuable building block for medicinal chemists exploring novel therapeutic agents.

The indole scaffold, a prominent motif in numerous natural products and pharmacologically active compounds, contributes to the broad spectrum of biological activities exhibited by derivatives of 7-Acetyl-1H-indole-2-carboxylic acid. Recent advancements in drug discovery have highlighted the compound's role in developing treatments for diverse diseases, including cancer, inflammation, and neurological disorders. The presence of both functional groups allows for further chemical modification, enabling the creation of structurally diverse analogs with tailored biological properties.

In the context of oncology research, 7-Acetyl-1H-indole-2-carboxylic acid has been investigated as a precursor for indole-derived inhibitors targeting specific kinases and transcription factors involved in tumor progression. Studies have demonstrated that its derivatives exhibit potent cytotoxic effects against various cancer cell lines, suggesting potential applications in developing next-generation anticancer therapies. The acetyl group on the indole ring provides a site for selective conjugation with other pharmacophores, enhancing drug-like properties such as solubility and bioavailability.

Moreover, the compound has garnered attention in the field of anti-inflammatory drug development. Researchers have leveraged its structural features to design molecules that modulate inflammatory pathways by inhibiting key enzymes like cyclooxygenase (COX) and lipoxygenase (LOX). Preclinical studies indicate that certain derivatives of 7-Acetyl-1H-indole-2-carboxylic acid exhibit significant anti-inflammatory activity without inducing notable side effects, making them promising candidates for further clinical evaluation.

The neurological domain has also seen considerable interest in 7-Acetyl-1H-indole-2-carboxylic acid and its derivatives. The indole core is well-known for its role in modulating neurotransmitter systems, particularly serotonin and dopamine pathways, which are implicated in conditions such as depression, anxiety, and Parkinson's disease. Recent research has shown that certain analogs derived from this compound exhibit neuroprotective effects by scavenging reactive oxygen species and reducing neuroinflammation. These findings open new avenues for developing novel therapeutics targeting neurodegenerative disorders.

The synthetic utility of 7-Acetyl-1H-indole-2-carboxylic acid extends beyond its biological applications. Its straightforward functionalization patterns make it an ideal candidate for exploring new synthetic methodologies and catalytic strategies. For instance, recent studies have explored palladium-catalyzed cross-coupling reactions involving this compound, leading to the efficient synthesis of complex indole derivatives with high regioselectivity. Such advancements not only enhance the accessibility of these compounds but also pave the way for innovative approaches in organic synthesis.

In conclusion, 7-Acetyl-1H-indole-2-carboxylic acid (CAS No. 133738-76-8) represents a cornerstone in modern pharmaceutical research due to its structural versatility and broad range of biological activities. Its role as a key intermediate in synthesizing bioactive molecules underscores its importance in drug discovery efforts aimed at addressing critical health challenges. As ongoing research continues to uncover new applications and synthetic possibilities, this compound is poised to remain at the forefront of medicinal chemistry innovation.

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