Chemistry:TAPI-1

TAPI-1
Names
	Systematic IUPAC name (2R)-N1-[(2S)-1-({(2S)-1-[(2-Aminoethyl)amino]-1-oxopropan-2-yl}amino)-3-(naphthalen-2-yl)-1-oxopropan-2-yl]-N4-hydroxy-2-(2-methylpropyl)butanediamide
	Other names N-{(2R)-2-[2-(Hydroxyamino)-2-oxoethyl]-4-methylpentanoyl}-3-(2-naphthyl)-L-alanyl-N-(2-aminoethyl)-L-alaninamide
Identifiers
CAS Number	163847-77-6;
3D model (JSmol)	Interactive image;
ChemSpider	8634035;
PubChem CID	10458621;
UNII	UVK3UP3V6Z ;
	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/s1 Key: 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/s1 Key: AWNBSWDIOCXWJW-WTOYTKOKBP;
	SMILES O=C(NCCN)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](CC(=O)NO)CC(C)C)Cc2ccc1c(cccc1)c2)C;
Properties
Chemical formula	C26H37N5O5
Molar mass	499.612 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

TAPI-1 ( TNF-alpha protease inhibitor I) is a structural analog of TAPI-0 with similar but more stable validness^{[clarification needed]} in vitro for the matrix metalloproteinases (MMPs) and TNF- alpha converting enzyme^[1] which blocks shedding of several cell surface proteins such as IL-6 and p60 TNF receptor.^[2]

References

↑ 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. PMID 7594530.
↑ "TAPI-1 biological activity". selleckchemicals. http://www.selleckchem.com/products/tapi-1.html.

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Names

Systematic IUPAC name (2R)-N¹-[(2S)-1-({(2S)-1-[(2-Aminoethyl)amino]-1-oxopropan-2-yl}amino)-3-(naphthalen-2-yl)-1-oxopropan-2-yl]-N⁴-hydroxy-2-(2-methylpropyl)butanediamide
Other names N-{(2R)-2-[2-(Hydroxyamino)-2-oxoethyl]-4-methylpentanoyl}-3-(2-naphthyl)-L-alanyl-N-(2-aminoethyl)-L-alaninamide
Identifiers
CAS Number	163847-77-6
3D model (JSmol)	Interactive image
ChemSpider	8634035
PubChem CID	10458621
UNII	UVK3UP3V6Z^Y
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/s1 Key: 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/s1 Key: AWNBSWDIOCXWJW-WTOYTKOKBP
SMILES O=C(NCCN)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](CC(=O)NO)CC(C)C)Cc2ccc1c(cccc1)c2)C
Properties
Chemical formula	C₂₆H₃₇N₅O₅
Molar mass	499.612 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references