Compound W - CAS 173550-33-9
Catalog number:
173550-33-9
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H12N2O8
Molecular Weight:
396.31
COA:
Inquire
Targets:
Amyloid-β | γ-secretase
Description:
Compound W, also called 3,5-bis(4-Nitrophenoxy)benzoic acid, a 3,3'-diiodothyronine sulfate cross-reactive substance, is an inhibitor of γ-secretase which causes a decrease in the released levels of Aβ42 and notch-1 Aβ-like peptide 25 (Nβ25).
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Brife Description:
Reduces Aβ42 levels; γ-secretase inhibitor
Appearance:
Yellow solid
Synonyms:
3,5-bis(4-Nitrophenoxy)benzoic acid; 173550-33-9; gamma-Secretase Modulator, CW; ACMC-1CUIP; SCHEMBL264541; CHEMBL1553155; CTK8B1007; JOSXKPZXMVHRKU-UHFFFAOYSA-; DTXSID10587892; JOSXKPZXMVHRKU-UHFFFAOYSA-N; HMS3269J17; ZINC2576957; ANW-22664; MFCD02093450; AKOS015833412; 3,5-bis (4-nitrophenoxy) benzoic acid; NCGC00167814-01; AJ-42568; AK-63150; EN002659; OR182673; KB-234083; TR-007681; B2120; Compound W|CW|3,5-Bis(4-nitrophenoxy)benzoic acid; BRD-K98143539-001-01-4; I14-62910
Solubility:
Soluble to 100 mM in DMSO, to 5 mM in ethanol, and to 5 mM in 1.1eq. NaOH.
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -23℃ for long term (months to years).
MSDS:
Inquire
Melting Point:
577.655℃ at 760 mmHg
Density:
1.485 g/cm3
InChIKey:
JOSXKPZXMVHRKU-UHFFFAOYSA-N
InChI:
1S/C19H12N2O8/c22-19(23)12-9-17(28-15-5-1-13(2-6-15)20(24)25)11-18(10-12)29-16-7-3-14(4-8-16)21(26)27/h1-11H,(H,22,23)
Canonical SMILES:
C1=CC(=CC=C1[N+](=O)[O-])OC2=CC(=CC(=C2)C(=O)O)OC3=CC=C(C=C3)[N+](=O)[O-]
1.Extent of M2 δ to ligand π-conjugation in neutral and mixed valence states of bis(4-isonicotinate)-bis(2,4,6-triisopropylbenzoate) dimetal complexes (MM), where M = Mo or W, and their adducts with tris(pentafluorophenyl)boron.
Bunting P1, Chisholm MH, Gallucci JC, Lear BJ. J Am Chem Soc. 2011 Apr 20;133(15):5873-81. doi: 10.1021/ja109522b. Epub 2011 Mar 24.
The reaction between W(2)(T(i)PB)(4), where T(i)PB = 2,4,6-triisopropylbenzoate, and 2 equiv of 4-isonicotinic acid (nicH) yields the compound W(2)(T(i)PB)(2)(nic)(2), 2, and T(i)PBH. Compound 2 is related to the previously reported molybdenum analog, Mo(2)(T(i)PB)(2)(nic)(2), 1. Compounds 1 and 2 react with 2 equiv of B(C(6)F(5))(3) in THF to form the adducts M(2)(T(i)PB)(2)(nic-B(C(6)F(5))(3))(2), 1B (M = Mo) and 2B (M = W), which have been crystallographically characterized as solvates M(2)(T(i)PB)(2)(nic-B(C(6)F(5))(3))(2)·2THF n-hexane. Compounds 1 and 2 are intensely colored due to M(2) δ to π* MLCT transitions, and upon complexation with B(C(5)F(5))(3) to give 1B and 2B, these bands shift to lower energy and gain in intensity. Each compound shows two one-electron ligand-based reductions with a ΔE(1/2) = 120 (1), 300 (1B), 440 (2), and 650 mV (2B). The larger ΔE(1/2) values for the tungsten compounds reflect the greater orbital mixing of the metal 5d-based M(2) δ and the nic π* LUMO.
2.Thyroid function and 3,3'-diiodothyronine sulfate cross-reactive substance (compound W) in maternal hyperthyroidism with antithyroid treatment.
Vanmiddlesworth L1, Vanmiddlesworth NR, Egerman RS, Bush AJ, Ramsey RD, Delmar LP, Ho EC, Wu SY. Endocr Pract. 2011 Mar-Apr;17(2):170-6. doi: 10.4158/EP09305.OR.
OBJECTIVE: To test whether the serial measurement of maternal levels of compound W, a 3,3'-diiodothyronine sulfate cross-reactive substance, can serve as a potential indicator of fetal thyroid function in pregnant women receiving antithyroid medication.
3.Monoanionic molybdenum and tungsten tris(dithiolene) complexes: a multifrequency EPR study.
Sproules S1, Banerjee P, Weyhermüller T, Yan Y, Donahue JP, Wieghardt K. Inorg Chem. 2011 Aug 1;50(15):7106-22. doi: 10.1021/ic2006265. Epub 2011 Jun 23.
Numerous Mo and W tris(dithiolene) complexes in varying redox states have been prepared and representative examples characterized crystallographically: [M(S(2)C(2)R(2))(3)](z) [M = Mo, R = Ph, z = 0 (1) or 1- (2); M = W, R = Ph, z = 0 (4) or 1- (5); R = CN, z = 2-, M = Mo (3) or W (6)]. Changes in dithiolene C-S and C-C bond lengths for 1 versus 2 and 4 versus 5 are indicative of ligand reduction. Trigonal twist angles (Θ) and dithiolene fold angles (α) increase and decrease, respectively, for 2 versus 1, 5 versus 4. Cyclic voltammetry reveals generally two reversible couples corresponding to 0/1- and 1-/2- reductions. The electronic structures of monoanionic molybdenum tris(dithiolene) complexes have been analyzed by multifrequency (S-, X-, Q-band) EPR spectroscopy. Spin-Hamiltonian parameters afforded by spectral simulation for each complex demonstrate the existence of two distinctive electronic structure types. The first is [Mo(IV)((A)L(3)(5-•))](1-) ((A)L = olefinic dithiolene, type A), which has the unpaired electron restricted to the tris(dithiolene) unit and is characterized by isotropic g-values and small molybdenum superhyperfine coupling.
4.(Acetonitrile-κN)penta-carbonyl-tungsten(0).
Strasser CE1, Cronje S, Raubenheimer HG. Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):m772. doi: 10.1107/S1600536811017879. Epub 2011 May 20.
The acetonitrile ligand in the title compound, [W(CH(3)CN)(CO)(5)], is coordinated end-on to a penta-carbonyl-tungsten(0) fragment with a W-N bond length of 2.186 (4) Å, completing an octa-hedral coordination environment around the W atom.
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CAS 173550-33-9 Compound W

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