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CS-W001157 4
Total: USD 88.00

2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole

  • CAS No. 6208-60-2

  • Cat. No. CS-W000373
  • Purity≥98%
  • MDL No.MFCD00464648

*For research and further manufacturing use only, not for direct human use.

2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole|CS-W000373

Structure of 6208-60-2

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General Information

  • CAS No. 6208-60-2
  • Cat. No. CS-W000373
  • Purity ≥98%
  • MDL No. MFCD00464648
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₂N₂
  • Molecular Weight 172.23
  • Synonym(s) 2,3,4,5-Tetrahydro-1H-Pyrido[4,3,b]Indole
  • SMILES C1(N2)=C(CNCC1)C3=C2C=CC=C3

Description

This tetrahydroindole scaffold delivers a rigid, electron-rich core ideal for medicinal chemistry applications. Its fused bicyclic structure enhances metabolic stability and facilitates π–π interactions in target binding. The saturated pyridine ring improves solubility and reduces off-target reactivity. This framework integrates seamlessly into kinase inhibitors and CNS-targeted compounds.

Application

2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole serves as a versatile heterocyclic building block in medicinal chemistry, offering a rigid, planar scaffold with defined nitrogen positioning. It functions as a core motif in the synthesis of bioactive compounds and enables straightforward derivatization at multiple sites. The compound exhibits good bench stability and compatibility with standard synthetic transformations, facilitating efficient access to complex molecular architectures in drug discovery programs.

Synthesis

  • Route1
    • 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole|CS-0967615
      6208-43-1
    • ~91%
    • In-stock
      2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole|CS-W000373
      6208-60-2

    References

    • Kalin, Jay H.; Butler, Kyle V.; Akimova, Tatiana; Hancock, Wayne W.; Kozikowski, Alan P. Journal of Medicinal Chemistry, 2012 , vol. 55, # 2 p. 639 - 651
  • Route2
    • Ethyl 3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate|CS-0062516
      63277-54-3
    • ~84%
    • In-stock
      2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole|CS-W000373
      6208-60-2

    References

    • Bonjoch, Josep; Diaba, Faiza; Pages, Lluis; Perez, Daniel; Soca, Lidia; Miralpeix, Montserrat; Vilella, Dolors; Anton, Paquita; Puig, Carles Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 15 p. 4299 - 4302
  • Route3
    • null|null
      3612-20-2
    • null|null
      100-63-0
    • ~%
    • In-stock
      2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole|CS-W000373
      6208-60-2

    References

    • WO2011/11186 A2, ; Page/Page column 62 ; WO 2011/011186 A2

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   27.82
  • LogP   1.8136
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   0

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