143547-74-4Relevant articles and documents
The coordination chemistry of the hydrotris(3-diphenylmethyl-pyrazol-1-yl)borate (TpCHPh2) ligand
Rheingold, Arnold L.,Liable-Sands, Louise M.,Golen, James A.,Yap, Glenn P.A.,Trofimenko, Swiatoslaw
, p. 598 - 604 (2004)
The new ligand, hydrotris[3-(diphenylmethyl)pyrazol-1-yl]borate, Tp CHPh2, has been synthesized and its coordination chemistry was compared with that of the analogous Tpipr. The new ligand was converted to a variety of complexes, such as M[TpCHPh2]X (M = Co, Ni, Zn: X = Cl, NCO, NCS), Pd[TpCHPh2][η3-methallyl], Co[TpCHPh2](acac), and Co[TpCHPh2](scorpionate ligand). Compounds Tl[TpCHPh2], 1, Co[TpCHPh2]Cl, 2, Co[Tp CHPh2](NCS)(DMF), 3, Ni[TpCHPh2](NCS)(DMF)2, 4, Co[TpCHPh2](acac), 5, Co[TpCHPh2][Ph2Bp], 6, Co[TpCHPh2][Bpph], 7, Co[TpCHPh2][Tp], 8, and (Ni[TpCHPh2])2[C2O4](H 2O)2, 9, were structurally characterized.
Nonprostanoid prostacyclin mimetics. 3. Structural variations of the diphenyl heterocycle moiety
Meanwell,Rosenfeld,Trehan,Romine,Wright,Brassard,Buchanan,Federici,Fleming,Gamberdella,Zavoico,Seiler
, p. 3498 - 3512 (2007/10/02)
4,5-Diphenyl-2-oxazolenonanoic acid (2) and 2-[3-[2-(4,5-diphenyl-2- oxazolyl)ethyl]phenoxy]acetic acid (3) were previously identified as nonprostanoid prostacyclin (PGI2) mimetics that inhibit ADP-induced aggregation of human platelets in vitro. The effects on biological activity of substitution and structural modification of the 4- and 5-phenyl rings of 3 was examined. Potency showed a marked sensitivity to the introduction of substituents to these aromatic rings and only the bis-4-methyl derivative 9j, IC50 = 0.34 μM, demonstrated enhanced potency compared to the parent structure 3, IC50 = 1.2 μM. Substitution at the ortho or meta positions of the phenyl rings, replacement by thiopheneyl or cyclohexyl moieties, or constraining in a planar phenanthrene system resulted in compounds that were less effective inhibitors of ADP-induced platelet aggregation. In contrast, variation of the heterocycle moiety revealed a much less stringent SAR and many 5- and 6-membered heterocycles were found to effectively substitute for the oxazole ring of 2 and 3. The diphenylmethyl moiety functioned as an effective isostere for 4,5-diphenylated heterocycles since 13aad showed similar platelet inhibitory activity to 3. With the exception of the 3,4,5- triphenylpyrazole derivative 13g, compounds presenting the (m- ethylphenoxy)acetic acid side chain discovered with 3 demonstrated enhanced potency compared to the analogously substituted alkanoic acid derivative. The structure-activity findings led to a refinement of a model of the nonprostanoid PGI2 mimetic pharmacophore.
