Cas no 58038-66-7 (Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate)

Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2H-Pyrido[4,3-b]Indole-2-Carboxylate is a fluorinated heterocyclic compound with a fused pyridoindole core. Its structure incorporates an ethyl ester group at the 2-position and a fluorine substituent at the 8-position, enhancing its reactivity and potential pharmacological properties. This compound is of interest in medicinal chemistry due to its rigid, polycyclic framework, which may improve binding affinity and selectivity in biological targets. The fluorine atom can influence electronic properties and metabolic stability, making it valuable for drug discovery applications. Its synthetic versatility allows for further derivatization, enabling the exploration of structure-activity relationships in therapeutic agent development.
Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate structure
58038-66-7 structure
Product Name:Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate
CAS No:58038-66-7
MF:C14H15FN2O2
MW:262.279506921768
MDL:MFCD02930345
CID:343347
PubChem ID:2764557
Update Time:2025-06-09

Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
    • 2H-Pyrido[4,3-b]indole-2-carboxylic acid, 8-fluoro-1,3,4,5-tetrahydro-,ethyl ester
    • 8-FLUORO-1,3,4,5-TETRAHYDRO-PYRIDO[4,3-B]INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
    • Ethyl 8-fluoro-1,3,4,5-tetrahydro-2H-pyrido-[4,3-b]indole-2-carboxylate
    • ETHYL 8-FLUORO-1,3,4,5-TETRAHYDRO-2H-PYRIDO[4,3-B]INDOLE-2-CARBOXYLATE
    • 2-carbethoxy-8-fluoro-1,2,3,4-tetrahydropyrido[4,3-b]indole
    • 2-carbethoxy-8-fluoro-2,3,4,5-tetrahydro-1H-pyrido<4,3-b>indole
    • OYAGMJMNTRNOCC-UHFFFAOYSA-N
    • 8-fluoro-2-carbethoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
    • 58038-66-7
    • Oprea1_819867
    • ethyl 8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylate
    • MFCD02930345
    • 9Y-0006
    • DTXSID50377496
    • ETHYL 8-FLUORO-1H,2H,3H,4H,5H-PYRIDO[4,3-B]INDOLE-2-CARBOXYLATE
    • Ethyl8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
    • SCHEMBL10777655
    • AKOS005071585
    • J-521235
    • CS-0453862
    • DB-401620
    • ethyl 8-fluoro-1H,3H,4H,5H-pyrido[4,3-b]indole-2-carboxylate
    • Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate
    • MDL: MFCD02930345
    • Inchi: 1S/C14H15FN2O2/c1-2-19-14(18)17-6-5-13-11(8-17)10-7-9(15)3-4-12(10)16-13/h3-4,7,16H,2,5-6,8H2,1H3
    • InChI Key: OYAGMJMNTRNOCC-UHFFFAOYSA-N
    • SMILES: FC1C=CC2=C(C=1)C1CN(C(=O)OCC)CCC=1N2

Computed Properties

  • Exact Mass: 262.11200
  • Monoisotopic Mass: 262.11175589g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 3
  • Complexity: 352
  • 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: 2.3
  • Topological Polar Surface Area: 45.3?2

Experimental Properties

  • Melting Point: 172-173
  • PSA: 45.33000
  • LogP: 2.75950
  • Sensitiveness: Light Sensitive

Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate Security Information

  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT

Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate 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%

Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate Pricemore >>

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Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate Production Method

Additional information on Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate

Research Brief on Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate (CAS: 58038-66-7)

Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate (CAS: 58038-66-7) is a fluorinated heterocyclic compound that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug discovery. This compound belongs to the class of tetrahydro-β-carboline derivatives, which are known for their diverse pharmacological activities, including serotonin receptor modulation, antimicrobial effects, and antitumor properties. The presence of a fluorine atom at the 8-position introduces unique electronic and steric properties, making it a promising scaffold for the development of novel therapeutic agents.

Recent studies have focused on the synthesis and biological evaluation of Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate. A 2023 publication in the Journal of Medicinal Chemistry reported an optimized synthetic route for this compound, achieving high yields and purity. The study highlighted the importance of the fluorine substituent in enhancing the compound's metabolic stability and binding affinity to target proteins. Computational modeling and molecular docking studies further revealed that the fluorinated derivative exhibits improved interactions with serotonin receptors compared to its non-fluorinated counterpart.

In vitro and in vivo pharmacological evaluations have demonstrated the compound's potential as a serotonin 5-HT2A receptor antagonist. A preclinical study published in Neuropharmacology (2024) showed that Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate significantly reduced anxiety-like behaviors in rodent models, suggesting its utility in the treatment of neuropsychiatric disorders. Additionally, the compound exhibited favorable pharmacokinetic properties, including good oral bioavailability and blood-brain barrier penetration.

Beyond its neurological applications, recent research has explored the anticancer potential of this compound. A 2024 study in Bioorganic & Medicinal Chemistry Letters reported that Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate inhibited the proliferation of several cancer cell lines, including breast and lung cancer, through the induction of apoptosis and cell cycle arrest. Mechanistic studies indicated that the compound modulates key signaling pathways, such as the PI3K/AKT and MAPK cascades, which are critical for cancer cell survival and proliferation.

Despite these promising findings, challenges remain in the development of Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate as a therapeutic agent. Issues such as off-target effects, potential toxicity, and scalability of synthesis need to be addressed in future studies. Ongoing research is focused on structural optimization to improve selectivity and reduce adverse effects. Collaborative efforts between academic institutions and pharmaceutical companies are expected to accelerate the translation of this compound into clinical trials.

In conclusion, Ethyl 8-Fluoro-1,3,4,5-Tetrahydro-2h-Pyrido4,3-BIndole-2-Carboxylate (CAS: 58038-66-7) represents a versatile and pharmacologically active scaffold with potential applications in neurology and oncology. Continued research into its mechanism of action and therapeutic potential will be crucial for its development as a novel drug candidate. The integration of advanced synthetic techniques, computational modeling, and rigorous biological testing will further elucidate its role in modern drug discovery.

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