142004-00-0Relevant academic research and scientific papers
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.
Synthesis of the acridone alkaloids glyfoline and congeners. Structure- activity relationship studies of cytotoxic acridones
Su,Kohler,Chou,Moon Woo Chun,Watanabe
, p. 2703 - 2710 (2007/10/02)
Glyfoline (4, 1,6-dihydroxy-10-methyl-2,3,4,5-tetramethoxyacridin-9-one) and its congeners were synthesized for evaluation of their cytotoxicity. A detailed structure-activity relationships (SAR) of these acridone derivatives were also studied. To study t
