SPD-304

  • CAT Number: I009569
  • CAS Number: 869998-49-2
  • Molecular Formula: C32H32F3N3O2
  • Molecular Weight: 547.622
  • Purity: ≥95%
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SPD-304 (CAT: I009569) is an inhibitor of tumor necrosis factor α (TNFα), specifically targeting its binding to the TNF receptor 1 (TNFR1). With an IC50 of 22 µM, SPD-304 effectively blocks the interaction between TNFα and TNFR1. TNFα is a cytokine involved in inflammatory processes and immune responses. The inhibition of TNFα signaling by SPD-304 may have implications in the treatment of conditions characterized by excessive TNFα activity, such as inflammatory disorders. Additionally, both TNFα and the angiotensin II/angiotensin II receptor type 1 (AT1) axis have been implicated in neuropathic pain and nociception, suggesting a potential role for SPD-304 in modulating these processes.

Catalog Number I009569
CAS Number 869998-49-2
Synonyms

SPD-304, SPD 304, SPD304.;6,7-dimethyl-3-[[methyl[2-[methyl[[1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl]methyl]amino]ethyl]amino]methyl]-4H-1-benzopyran-4-one

Molecular Formula

C32H32F3N3O2

Purity 95%
Target TNFα inhibitor
Solubility Soluble in DMSO
Storage -20°C
IUPAC Name 6,7-dimethyl-3-[[methyl-[2-[methyl-[[1-[3-(trifluoromethyl)phenyl]indol-3-yl]methyl]amino]ethyl]amino]methyl]chromen-4-one
InChI InChI=1S/C32H32F3N3O2/c1-21-14-28-30(15-22(21)2)40-20-24(31(28)39)18-37(4)13-12-36(3)17-23-19-38(29-11-6-5-10-27(23)29)26-9-7-8-25(16-26)32(33,34)35/h5-11,14-16,19-20H,12-13,17-18H2,1-4H3
InChIKey JZNXLPPJRFFECJ-UHFFFAOYSA-N
SMILES CC1=C(C=C2C(=C1)C(=O)C(=CO2)CN(C)CCN(C)CC3=CN(C4=CC=CC=C43)C5=CC=CC(=C5)C(F)(F)F)C
Reference

1:Arch Pharm (Weinheim). 2014 Nov;347(11):798-805. doi: 10.1002/ardp.201400198. Epub 2014 Aug 27. Rationally designed less toxic SPD-304 analogs and preliminary evaluation of their TNF inhibitory effects.Alexiou P,Papakyriakou A,Ntougkos E,Papaneophytou CP,Liepouri F,Mettou A,Katsoulis I,Maranti A,Tsiliouka K,Strongilos A,Chaitidou S,Douni E,Kontopidis G,Kollias G,Couladouros E,Eliopoulos E, PMID: 25160057 DOI: 10.1002/ardp.201400198 </br><span>Abstract:</span> SPD-304 was discovered as a promising tumor necrosis factor alpha (TNF) antagonist that promotes dissociation of TNF trimers and therefore blocks the interaction of TNF and its receptor. However, SPD-304 contains a potentially toxic 3-alkylindole moiety, which can be bioactivated to a reactive electrophilic intermediate. A series of SPD-304 analogs was synthesized with the aim to diminish its toxicophore groups while maintaining the binding affinity for TNF. Incorporation of electron-withdrawing substituents at the indole moiety, in conjunction with elimination of the 6/’-methyl group of the 4-chromone moiety, led to a significantly less toxic and equally potent TNF inhibitor.© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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