53544-70-0Relevant academic research and scientific papers
Practical Continuous-Flow Trapping Metalations of Functionalized Arenes and Heteroarenes Using TMPLi in the Presence of Mg, Zn, Cu, or la Halides
Becker, Matthias R.,Knochel, Paul
supporting information, p. 12501 - 12505 (2015/10/12)
The flow metalation of various arenes and heteroarenes involving an in situ trapping with metal salts (ZnCl2. LiCl, MgCl2, CuCN. LiCl, LaCl3. LiCl) under very convenient conditions (0 ?C, 40 s) is reported. The resulting Mg, Zn, Cu, or La organic species are trapped with various electrophiles in high yields. In several cases, unusual kinetically controlled regioselectivities are obtained. All these flow metalations can be scaled up simply by extending the reaction time and without further optimization. The reaction scope of such flow metalations is considerably broader than that of the corresponding batch procedures.
Design, synthesis and structure-activity relationship of rhenium 2-arylbenzothiazoles as β-amyloid plaque binding agents
Pan, Jinhe,Mason, Neale S.,Debnath, Manik L.,Mathis, Chester A.,Klunk, William E.,Lin, Kuo-Shyan
, p. 1720 - 1726 (2013/04/10)
To continue our efforts toward the development of 99mTc PiB analogs, we have synthesized 24 neutral and lipophilic Re (as a surrogate of 99mTc) 2-arylbenzothiazoles, and explored their structure-activity relationship for binding to Aβ1-40 fibrils. These Re complexes were designed and synthesized via the integrated approach, so their 99mTc analogs would have a greater chance of crossing the blood-brain barrier. While the lipophilicities (log PC18 = 1.59-3.53) of these Re 2-arylbenzothiazoles were all within suitable range, their binding affinities (Ki = 30-617 nM) to Aβ1-40 fibrils varied widely depending on the selection and integration of the tetradentate chelator into the 2-phenylbenzothiazole pharmacophore. For potential clinical applications, further refinement to obtain Re 2-arylbenzothiazoles with better binding affinities (99mTc analogs for more widespread application via the use of SPECT scanners.
Structure-activity relationships of benzimidazoles and related heterocycles as topoisomerase I poisons
Kim, Jung Sun,Sun, Qun,Gatto, Barbara,Yu, Chiang,Liu, Angela,Liu, Leroy F.,LaVoie, Edmond J.
, p. 621 - 630 (2007/10/03)
A series of substituted 2-(4-methoxyphenyl)-1H-benzimidazoles were synthesized and evaluated as inhibitors of topoisomerase I. The presence of a 5-formyl-, 5-(aminocarbonyl)-, or 5-nitro group (i.e., substituents capable of acting as hydrogen bond accepters) correlated with the potential of select derivatives to inhibit topoisomerase I. In contrast to bi- and terbenzimidazoles, the substituted benzimidazoles that were active as topoisomerase I poisons exhibited minimum or no DNA binding affinity. 5-Nitro-2-(4-methoxyphenyl)-1H-benzimidazole exhibited the highest activity and was significantly more active than the 4-nitro positional isomer. The 5- and 6-nitro derivatives of 2-(4-methoxyphenyl)benzoxazole, 2-(4-methoxyphenyl)benzothiazole, and 2-(4-methoxyphenyl)indole were synthesized and their relative activity as topoisomerase I inhibitors determined. None of these heterocyclic analogues were effective in significantly inhibiting cleavable-complex formation in the presence of DNA and topoisomerase I, suggesting a high degree of structural specificity associated with the interaction of these substituted benzimidazoles with the enzyme or the enzyme-DNA complex. In evaluating their cytotoxicity, these new topoisomerase I poisons also exhibited no significant cross-resistance against cell lines that express camptothecin-resistant topoisomerase I.
