189700-10-5Relevant academic research and scientific papers
Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin
Almabruk, Khaled H.,Chang, Jeff H.,Mahmud, Taifo
, p. 2391 - 2396 (2016)
On the basis of its reported chemical structure, perbergin, a Rhodococcus fascians virulence quencher from the bark of Dalbergia pervillei, and its isomer were synthesized in nine steps with a 13.5% yield. However, the NMR spectra of the synthetic product
Correlation of hydrogen-bonding propensity and anticancer profile of tetrazole-tethered combretastatin analogues
Jedhe, Ganesh S.,Paul, Debasish,Gonnade, Rajesh G.,Santra, Manas K.,Hamel, Ernest,Nguyen, Tam Luong,Sanjayan, Gangadhar J.
, p. 4680 - 4684 (2013/08/15)
A series of 1,5-disubstituted tetrazole-tethered combretastatin analogues with extended hydrogen-bond donors at the ortho-positions of the aryl A and B rings were developed and evaluated for their antitubulin and antiproliferative activity. We wanted to test whether intramolecular hydrogen-bonding used as a conformational locking element in these analogues would improve their activity. The correlation of crystal structures with the antitubulin and antiproliferative profiles of the modified analogues suggested that hydrogen-bond-mediated conformational control of the A ring is deleterious to the bioactivity. In contrast, although there was no clear evidence that intramolecular hydrogen bonding to the B ring enhanced activity, we found that increased substitution on the B ring had a positive effect on antitubulin and antiproliferative activity. Among the various analogues synthesized, compounds 5d and 5e, having hydrogen-bonding donor groups at the ortho and meta-positions on the 4-methoxy phenyl B ring, are strong inhibitors of tubulin polymerization and antiproliferative agents having IC50 value in micromolar concentrations.
Design, synthesis and biological evaluation of dihydronaphthalene and benzosuberene analogs of the combretastatins as inhibitors of tubulin polymerization in cancer chemotherapy
Sriram, Madhavi,Hall, John J.,Grohmann, Nathan C.,Strecker, Tracy E.,Wootton, Taylor,Franken, Andreas,Trawick, Mary Lynn,Pinney, Kevin G.
, p. 8161 - 8171 (2008/12/23)
A novel series of dihydronaphthalene and benzosuberene analogs bearing structural similarity to the combretastatins in terms of 1,2-diarylethene, trimethoxyphenyl, and biaryl functionality has been synthesized. The compounds have been evaluated in regard
A biomimetic synthesis of stizolobinic acid
Baldwin, Jack E.,Spyvee, Mark R.,Whitehead, Roger C.
, p. 2771 - 2774 (2007/10/03)
Stizolobinic acid (1) was synthesized in a biomimetic fashion from an analogue of L-DOPA via an oxidative cleavage reaction.
