87654-45-3Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling of aryl chlorides with O, N-chelate stabilized diarylborinates
Zhang, Nan,Wang, Chen,Zou, Gang,Tang, Jie
, p. 54 - 58 (2017)
A series of O, N-chelated diarylborinates have been prepared and tested as arylboron counterpart alternative to oxygen-labile diarylborinic acids in palladium catalyzed Suzuki coupling of aryl chlorides. 3-Dimethylaminopropyl diarylborinates (B-5a), featuring a six-membered O, N-chelated boron ring that was confirmed by single crystal X-ray diffraction, displayed a delicately balanced stability and reactivity. Their cross-coupling with structurally various aryl chlorides could be effected as efficiently as that of the parent diarylborinic acids by using 0.1～1mol% Pd(OAc)2/IPr/P(OPh)3 as catalyst system, to provide the corresponding biaryls in good to excellent yields.
Design, synthesis and pharmacological characterization of analogs of 2-aminoethyl diphenylborinate (2-APB), a known store-operated calcium channel blocker, for inhibition of TRPV6-mediated calcium transport
Hofer, Alexandre,Kovacs, Gergely,Zappatini, Anna,Leuenberger, Michele,Hediger, Matthias A.,Lochner, Martin
, p. 3202 - 3213 (2013/07/11)
2-Aminoethyl diphenylborinate (2-APB) is a known modulator of the IP 3 receptor, the calcium ATPase SERCA, the calcium release-activated calcium channel Orai and TRP channels. More recently, it was shown that 2-APB is an efficient inhibitor of the epithelial calcium channel TRPV6 which is overexpressed in prostate cancer. We have conducted a structure-activity relationship study of 2-APB congeners to understand their inhibitory mode of action on TRPV6. Whereas modifying the aminoethyl moiety did not significantly change TRPV6 inhibition, substitution of the phenyl rings of 2-APB did. Our data show that the diaryl borinate moiety is required for biological activity and that the substitution pattern of the aryl rings can influence TRPV6 versus SOCE inhibition. We have also discovered that 2-APB is hydrolyzed and transesterified within minutes in solution.
