PYR-41

PYR-41
Names
	Preferred IUPAC name Ethyl 4-{(4Z)-4-[(5-nitrofuran-2-yl)methylidene]-3,5-dioxopyrazolidin-1-yl}benzoate
Identifiers
CAS Number	418805-02-4;
3D model (JSmol)	Interactive image;
ChemSpider	4492747;
ECHA InfoCard	100.213.089
PubChem CID	5335621;
UNII	HT54RAN9JZ ;
CompTox Dashboard (EPA)	DTXSID30416554 ;
	InChI InChI=1S/C17H13N3O7/c1-2-26-17(23)10-3-5-11(6-4-10)19-16(22)13(15(21)18-19)9-12-7-8-14(27-12)20(24)25/h3-9H,2H2,1H3,(H,18,21)/b13-9- Key: ARGIPZKQJGFSGQ-LCYFTJDESA-N;
	SMILES CCOC(=O)C1=CC=C(C=C1)N2C(=O)/C(=C\C3=CC=C(O3)[N ](=O)[O-])/C(=O)N2;
Properties
Chemical formula	C17H13N3O7
Molar mass	371.3 g/mol
Density	1.5±0.1 g/cm3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

PYR-41 is a cell permeable irreversible inhibitor of ubiquitin-activating enzyme E1.^[1] It was also reported to increase sumoylation in cells.^[1]^[2]

PYR-41 also blocks the downstream ubiquitination and ubiquitination-dependent protein degradation or other ubiquitination-mediated cellular activities. In addition, PYR-41 inhibits degradation of p53, a tumour suppressor.^[3]

References

^ ^a ^b Yang, Yili; Kitagaki, Jirouta; Dai, Ren-Ming; Tsai, Yien Che; Lorick, Kevin L.; Ludwig, Robert L.; Pierre, Shervon A.; Jensen, Jane P.; Davydov, Ilia V.; Oberoi, Pankaj; Li, Chou-Chi H.; Kenten, John H.; Beutler, John A.; Vousden, Karen H.; Weissman, Allan M. (1 October 2007). "Inhibitors of Ubiquitin-Activating Enzyme (E1), a New Class of Potential Cancer Therapeutics". Cancer Research. 67 (19): 9472–9481. doi:10.1158/0008-5472.CAN-07-0568. PMID 17909057.9472-9481&rft.date=2007-10-01&rft_id=info:doi/10.1158/0008-5472.CAN-07-0568&rft_id=info:pmid/17909057&rft.aulast=Yang&rft.aufirst=Yili&rft.au=Kitagaki, Jirouta&rft.au=Dai, Ren-Ming&rft.au=Tsai, Yien Che&rft.au=Lorick, Kevin L.&rft.au=Ludwig, Robert L.&rft.au=Pierre, Shervon A.&rft.au=Jensen, Jane P.&rft.au=Davydov, Ilia V.&rft.au=Oberoi, Pankaj&rft.au=Li, Chou-Chi H.&rft.au=Kenten, John H.&rft.au=Beutler, John A.&rft.au=Vousden, Karen H.&rft.au=Weissman, Allan M.&rft_id=https://doi.org/10.1158%2F0008-5472.CAN-07-0568&rfr_id=info:sid/en.wikipedia.org:PYR-41" class="Z3988">
^ Kapuria V, Peterson LF, Showalter HD, et al. (Aug 15, 2011). "Protein cross-linking as a novel mechanism of action of a ubiquitin-activating enzyme inhibitor with anti-tumor activity". Biochem Pharmacol. 82 (4): 341–349. doi:10.1016/j.bcp.2011.05.012. PMID 21621524.341-349&rft.date=2011-08-15&rft_id=info:doi/10.1016/j.bcp.2011.05.012&rft_id=info:pmid/21621524&rft.aulast=Kapuria&rft.aufirst=V&rft.au=Peterson, LF&rft.au=Showalter, HD&rfr_id=info:sid/en.wikipedia.org:PYR-41" class="Z3988">
^ Chen C, et al. (Jun 2014). "Ubiquitin-activating enzyme E1 inhibitor PYR-41 attenuates angiotensin II-induced activation of dendritic cells via the IκBa/NF-κB and MKP1/ERK/STAT1 pathways". Immunology. 142 (2): 307–319. doi:10.1111/imm.12255. PMC 4008238. PMID 24456201.307-319&rft.date=2014-06&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4008238#id-name=PMC&rft_id=info:pmid/24456201&rft_id=info:doi/10.1111/imm.12255&rft.aulast=Chen&rft.aufirst=C&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4008238&rfr_id=info:sid/en.wikipedia.org:PYR-41" class="Z3988">

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[yang_2007-1] Yang, Yili; Kitagaki, Jirouta; Dai, Ren-Ming; Tsai, Yien Che; Lorick, Kevin L.; Ludwig, Robert L.; Pierre, Shervon A.; Jensen, Jane P.; Davydov, Ilia V.; Oberoi, Pankaj; Li, Chou-Chi H.; Kenten, John H.; Beutler, John A.; Vousden, Karen H.; Weissman, Allan M. (1 October 2007). "Inhibitors of Ubiquitin-Activating Enzyme (E1), a New Class of Potential Cancer Therapeutics". Cancer Research. 67 (19): 9472–9481. doi:10.1158/0008-5472.CAN-07-0568. PMID 17909057.9472-9481&rft.date=2007-10-01&rft_id=info:doi/10.1158/0008-5472.CAN-07-0568&rft_id=info:pmid/17909057&rft.aulast=Yang&rft.aufirst=Yili&rft.au=Kitagaki, Jirouta&rft.au=Dai, Ren-Ming&rft.au=Tsai, Yien Che&rft.au=Lorick, Kevin L.&rft.au=Ludwig, Robert L.&rft.au=Pierre, Shervon A.&rft.au=Jensen, Jane P.&rft.au=Davydov, Ilia V.&rft.au=Oberoi, Pankaj&rft.au=Li, Chou-Chi H.&rft.au=Kenten, John H.&rft.au=Beutler, John A.&rft.au=Vousden, Karen H.&rft.au=Weissman, Allan M.&rft_id=https://doi.org/10.1158%2F0008-5472.CAN-07-0568&rfr_id=info:sid/en.wikipedia.org:PYR-41" class="Z3988">

[2] Kapuria V, Peterson LF, Showalter HD, et al. (Aug 15, 2011). "Protein cross-linking as a novel mechanism of action of a ubiquitin-activating enzyme inhibitor with anti-tumor activity". Biochem Pharmacol. 82 (4): 341–349. doi:10.1016/j.bcp.2011.05.012. PMID 21621524.341-349&rft.date=2011-08-15&rft_id=info:doi/10.1016/j.bcp.2011.05.012&rft_id=info:pmid/21621524&rft.aulast=Kapuria&rft.aufirst=V&rft.au=Peterson, LF&rft.au=Showalter, HD&rfr_id=info:sid/en.wikipedia.org:PYR-41" class="Z3988">

[3] Chen C, et al. (Jun 2014). "Ubiquitin-activating enzyme E1 inhibitor PYR-41 attenuates angiotensin II-induced activation of dendritic cells via the IκBa/NF-κB and MKP1/ERK/STAT1 pathways". Immunology. 142 (2): 307–319. doi:10.1111/imm.12255. PMC 4008238. PMID 24456201.307-319&rft.date=2014-06&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4008238#id-name=PMC&rft_id=info:pmid/24456201&rft_id=info:doi/10.1111/imm.12255&rft.aulast=Chen&rft.aufirst=C&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4008238&rfr_id=info:sid/en.wikipedia.org:PYR-41" class="Z3988">

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