16994-31-3Relevant academic research and scientific papers
Solvent-free friedel-crafts cyclization with trichloroacetic anhydride
Andrews, Ben,Bullock, Kae,Condon, Shannon,Corona, John,Davis, Roman,Grimes, John,Hazelwood, Andrew,Tabet, Elie
, p. 2664 - 2673 (2009)
Friedel-Crafts cyclization products were obtained using 1.1 equivalents of environmentally benign trichloroacetic anhydride as sole reagent and solvent. The resulting ketones included benzothiepins, benzothiopyrans, benzoxepins, dibenzothiepins, dibenzoxepins, and tetralones.
Discovery of Novel 4-Arylisochromenes as Anticancer Agents Inhibiting Tubulin Polymerization
Li, Wenlong,Shuai, Wen,Xu, Feijie,Sun, Honghao,Xu, Shengtao,Yao, Hong,Liu, Jie,Yao, Hequan,Zhu, Zheying,Xu, Jinyi
, p. 974 - 979 (2018/10/15)
XJP-L (8), a derivative of the natural product (±)-7,8-dihydroxy-3-methylisochroman-4-one isolated from the peel of Musa sapien tum L., was found to exhibit weak inhibitory activity of tubulin polymerization (IC50 = 10.6 μM) in our previous studies. Thus, a series of 4-arylisochromene derivatives were prepared by incorporating the trimethoxyphenyl moiety into 8, among which compound (±)-19b was identified as the most potent compound with IC50 values ranging from 10 to 25 nM against a panel of cancer cell lines. Further mechanism studies demonstrated that (±)-19b disrupted the intracellular microtubule network, caused G2/M phase arrest, induced cell apoptosis, and depolarized mitochondria of K562 cells. Moreover, (±)-19b exhibited potent in vitro antivascular and in vivo antitumor activities. Notably, the R-configured enantiomer of (±)-19b, which was prepared by chiral separation, was slightly more potent than (±)-19b and was much more potent than the S-configured enantiomer in both antiproliferative and antitubulin assays. Our findings suggest that (±)-19b deserves further research as a potential antitubulin agent for the treatment of cancers.
Benzopyranopyrazolyl derivatives for the treatment of inflammation
-
, (2008/06/13)
A class of benzopyranopyrazolyl derivatives is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I STR1 wherein A is --(CH2)m --X--(CH2)n --; wherein X is S(O)p or O; wherein m is 0 or 1; wherein n is 0 or 1; wherein p is 0 or 1; wherein B is selected from phenyl and five and six membered heteroaryl; wherein R1 is selected from lower haloalkyl, cyano, formyl, lower alkoxycarbonyl, lower alkoxy, lower N-alkylaminocarbonyl, N-phenylaminocarbonyl, lower N,N-dialkylaminocarbonyl and lower N-alkyl-N-phenylaminocarbonyl; wherein R2 is phenyl substituted at a substitutable position with a radical selected from lower alkylsulfonyl and sulfamyl; and wherein R4 is one or more radicals selected from hydrido, halo, lower alkylthio, lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, aminocarbonyl, lower haloalkyl, hydroxyl, lower alkoxy, amino, lower N-alkylamino, lower N,N-dialkylamino, lower hydroxyalkyl and lower haloalkoxy; or a pharmaceutically-acceptable salt thereof.
Conformationally restricted 1,5-diarylpyrazoles are selective COX-2 inhibitors
Bertenshaw, Stephen R.,Talley, John J.,Rogier,Graneto, Matthew J.,Koboldt, Carol M.,Zhang, Yan
, p. 2827 - 2830 (2007/10/03)
Benzothiopyranopyrazoles and benzopyranopyrazoles containing either a sulfone or sulfonamide moiety were synthesized and tested for COX-1 and COX-2 inhibition. This new class of COX-2 selective inhibitors possess antiinflammatory activity in vivo.
A Study of Electronic Effects Involving Electron Deficient Nitrogen : Part IV - Schmidt & Beckmann Rearrangements of Isoquinolinones & Isothiachromanone
Venugopal, V. K.,Rao, Nagabhushan,Rahman, M. F.,Bhalerao, U. T.
, p. 156 - 157 (2007/10/02)
Schmidt and Beckmann rearrangements of isoquinolinones (1,2) and isothiachromanone (3) afford exclusively seven-membered lactams (4,5,6) resulting from aryl bond migration.No alkyl bond migration is observed as in chromanones.
