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TAPI-1

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TAPI-1
Names
Systematic IUPAC name (2R)-N--1-oxopropan-2-yl}amino)-3-(naphthalen-2-yl)-1-oxopropan-2-yl]-N-hydroxy-2-(2-methylpropyl)butanediamide
Other names N-{(2R)-2--4-methylpentanoyl}-3-(2-naphthyl)-L-alanyl-N-(2-aminoethyl)-L-alaninamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C26H37N5O5/c1-16(2)12-21(15-23(32)31-36)25(34)30-22(26(35)29-17(3)24(33)28-11-10-27)14-18-8-9-19-6-4-5-7-20(19)13-18/h4-9,13,16-17,21-22,36H,10-12,14-15,27H2,1-3H3,(H,28,33)(H,29,35)(H,30,34)(H,31,32)/t17-,21+,22-/m0/s1Key: AWNBSWDIOCXWJW-WTOYTKOKSA-N
  • InChI=1/C26H37N5O5/c1-16(2)12-21(15-23(32)31-36)25(34)30-22(26(35)29-17(3)24(33)28-11-10-27)14-18-8-9-19-6-4-5-7-20(19)13-18/h4-9,13,16-17,21-22,36H,10-12,14-15,27H2,1-3H3,(H,28,33)(H,29,35)(H,30,34)(H,31,32)/t17-,21+,22-/m0/s1Key: AWNBSWDIOCXWJW-WTOYTKOKBP
SMILES
  • O=C(NCCN)(NC(=O)(NC(=O)(CC(=O)NO)CC(C)C)Cc2ccc1c(cccc1)c2)C
Properties
Chemical formula C26H37N5O5
Molar mass 499.612 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

TAPI-1 ( TNF-alpha protease inhibitor I) is a structural analog of TAPI-0 with similar but more stable validness in vitro for the matrix metalloproteinases (MMPs) and TNF- alpha converting enzyme which blocks shedding of several cell surface proteins such as IL-6 and p60 TNF receptor.

References

  1. Müllberg J rt al; Durie; Otten-Evans; Alderson; Rose-John; Cosman; Black; Mohler (Dec 1, 1995). "A metalloprotease inhibitor blocks shedding of the IL-6 receptor and the p60 TNF receptor". J Immunol. 155 (11): 5198–5205. doi:10.4049/jimmunol.155.11.5198. PMID 7594530.
  2. "TAPI-1 biological activity". selleckchemicals.
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