31462-59-6Relevant articles and documents
Solvent Polarity Predictably Tunes Spin Crossover T1/2 in Isomeric Iron(II) Pyrimidine Triazoles
Rodríguez-Jiménez, Santiago,Barltrop, Alexis S.,White, Nicholas G.,Feltham, Humphrey L. C.,Brooker, Sally
, p. 6266 - 6282 (2018)
Two isomeric pyrimidine-based Rdpt-type triazole ligands were made: 4-(4-methylphenyl)-3-(2-pyrimidyl)-5-phenyl-4H-1,2,4-triazole (L2pyrimidine) and 4-(4-methylphenyl)-3-(4-pyrimidyl)-5-phenyl-4H-1,2,4-triazole (L4pyrimidine). When reacted with [FeII(pyridine)4(NCE)2], where E = S, Se, or BH3, two families of mononuclear iron(II) complexes are obtained, including six solvatomorphs, giving a total of 12 compounds: [FeII(L2pyrimidine)2(NCS)2] (1), [FeII(L2pyrimidine)2(NCSe)2] (2), 2·1.5H2O, [FeII(L2pyrimidine)2(NCBH3)2]·2CHCl3 (3·2CHCl3), 3 and 3·2H2O, [FeII(L4pyrimidine)2(NCS)2] (4), 4·H2O, [FeII(L4pyrimidine)2(NCSe)2] (5), 5·2CH3OH, 5·1.5H2O, and [FeII(L4pyrimidine)2(NCBH3)2]·2.5H2O (6·2.5H2O). Single-crystal X-ray diffraction reveals that the N6-coordinated iron(II) centers in 1, 2, 3·2CHCl3, 4, 5, and 5·2CH3OH have two bidentate triazole ligands equatorially bound and two axial NCE co-ligands trans-coordinated. All structures are high spin (HS) at 100 K, except 3·2CHCl3, which is low spin (LS). Solid-state magnetic measurements show that only 3·2CHCl3 (T1/2 above 400 K) and 5·1.5H2O (T1/2 = 110 K) undergo spin crossover (SCO); the others remain HS at 300-50 K. When 3·2CHCl3 is heated at 400 K it desorbs CHCl3 becoming 3, which remains HS at 400-50 K. UV-Vis studies in CH2Cl2, CHCl3, (CH3)2CO, CH3CN, and CH3NO2 solutions for the BH3 analogues 3 and 6 led to a 6:1 ratio of Lnpyrimidine/Fe(II) being employed for the solution studies. These revealed SCO activity in all five solvents, with T1/2 values for the 2-pyrimidine complex (247-396 K) that were consistently higher than for the 4-pyrimidine complex (216-367 K), regardless of solvent choice, consistent with the 2-pyrimidine ring providing a stronger ligand field than the 4-pyrimidine ring. Strong correlations of solvent polarity index with the T1/2 values in those solvents are observed for each complex, enabling predictable T1/2 tuning by up to 150 K. While this correlation is tantalizing, here it may also be reflecting solvent-dependent speciation - so future tests of this concept should employ more stable complexes. Differences between solid-state (ligand field; crystal packing; solvent content) and solution (ligand field; solvation; speciation) effects on SCO are highlighted.
Synthesis and evaluation of the 2-aminothiazoles as anti-tubercular agents
Kesicki, Edward A.,Bailey, Mai A.,Ovechkina, Yulia,Early, Julie V.,Alling, Torey,Bowman, Julie,Zuniga, Edison S.,Dalai, Suryakanta,Kumar, Naresh,Masquelin, Thierry,Hipskind, Philip A.,Odingo, Joshua O.,Parish, Tanya
, (2016/06/01)
The 2-aminothiazole series has anti-bacterial activity against the important global pathogen Mycobacterium tuberculosis. We explored the nature of the activity by designing and synthesizing a large number of analogs and testing these for activity against M. tuberculosis, as well as eukaryotic cells. We determined that the C-2 position of the thiazole can accommodate a range of lipophilic substitutions, while both the C-4 position and the thiazole core are sensitive to change. The series has good activity against M. tuberculosis growth with sub-micromolar minimum inhibitory concentrations being achieved. A representative analog was selective for mycobacterial species over other bacteria and was rapidly bactericidal against replicating M. tuberculosis. The mode of action does not appear to involve iron chelation. We conclude that this series has potential for further development as novel antitubercular agents.
Pyruvamide Compounds as Inhibitors of Dust Mite Group 1 Peptidase Allergen and Their Use
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, (2013/02/27)
The present invention pertains generally to the field of therapeutic compounds and more specifically to certain pyruvamide compounds of the formula (X) (for convenience, collectively referred to herein as “PVA compounds”), which, inter alia, inhibit a dust mite Group 1 peptidase allergen (e.g., Der p 1, Der f 1, Eur m 1). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit a dust mite Group 1 peptidase allergen, and in the treatment of diseases and disorders that are mediated by a dust mite Group 1 peptidase allergen; that are ameliorated by the inhibition of a dust mite Group 1 peptidase allergen; asthma; rhinitis; allergic conjunctivitis; atopic dermatitis; an allergic condition which is triggered by dust mites; an allergic condition which is triggered by a dust mite Group 1 peptidase allergen; and canine atopy.