69470-84-4Relevant academic research and scientific papers
Novel Nitric Oxide Donors of Phenylsulfonylfuroxan and 3-Benzyl Coumarin Derivatives as Potent Antitumor Agents
Guo, Yalan,Wang, Yujie,Li, Haihong,Wang, Ke,Wan, Qi,Li, Jia,Zhou, Yubo,Chen, Ying
, p. 502 - 506 (2018/05/14)
In this work, five new hybrids of phenylsulfonylfuroxan merging 3-benzyl coumarin and their seco-B-ring derivatives 2-6 were designed and synthesized. Among them, compound 3 showed the most potent antiproliferation activities with IC50 values range from 0.5 to 143 nM against nine drug-sensitive and four drug-resistant cancer cell lines. Preliminary pharmacologic studies showed that these compounds displayed lower toxicities than that of lead compound 1. Compound 3 obviously induced the early apoptosis and hardly affected the cell cycle of A2780, which was significantly different from compound 1. Especially, it gave 559- and 294-fold selectivity antiproliferation activity in P-gp overexpressed drug-resistant cancer cell lines MCF-7/ADR and KB-V compared to their drug-sensitive ones MCF-7 and KB, implying that compounds 2-6 might have an extra mechanism of anti-MDR-cancer with P-gp overexpression.
Inhibitors of prostaglandin biosynthesis from Dalbergia odorifera
Goda,Kiuchi,Shibuya,Sankawa
, p. 2452 - 2457 (2007/10/02)
The root heartwood of Dalbergia odorifera T. CHEN (Leguminosae) is a Chinese medicinal drug (Japanese name koshinko) used for a stagnant blood syndrome (stagnation of disordered blood; Japanese, oketsu). In addition to 10 known compounds, five new phenolic compounds, isomucronustyrene and hydroxyobtustyrene (cinnamylphenols), (+)-isoduartin (isoflavan), odoriflavene (isoflav-3-ene) and (-)-odoricarpan (pterocarpan) were isolated and their structures were elucidated on the basis of chemical and spectroseopic methods. Of the fifteen compounds isolated, cinnamylphenols, isoflavans, isoflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.
FLAVONOID AND OTHER CONSTITUENTS OF BAUHINIA MANCA
Achenbach, Hans,Stoecker, Markus,Constenla, Manuel A.
, p. 1835 - 1842 (2007/10/02)
Phytochemical analysis of the stem of Bauhinia manca yielded 63 compounds, among them six new natural products.Major constituents were found to be 3-O-galloylepicatechin, gallic acid, cinnamic acid, β-sitosterol and its β-D-glucoside.The two new flavans possess significant antifungal activity.Key Word Index-Bauhinia manca; Leguminosae; 5,5-dimethoxylariciresinol; 4-O-methylisoliquiritigenin; 4'-O-methylliquiritigenin; 7,3'-dimethoxy-4-hydroxyflavan; 3',4'-dihydroxy-7-methoxyflavan; 2,4'-dihydroxy-4-methoxydihydrochalcone; antimicrobial activity.
Condensation of Phenols and Cinnamic Acids in Presence of Polyphosphoric Acid: A Novel Biogenetic-type Oxidative Self-cyclisation of p-Methoxycinnamic Acid to 7-Methoxycoumarin
Talapatra, Bani,Deb, Tulika,Talapatra, Sunil
, p. 1122 - 1125 (2007/10/02)
The course of PPA condensation/cyclisation of different phenols and cinnamic acids has been found to depend upon the nature of the substrate, stoichiometry, composition of PPA, and reaction condition.Condensation of phloroglucinol (50-70 deg C, 1 hr) with cinnamic acid in the presence of PPA leads to pinocembrin (I) (50percent) and 5-hydroxy-4,8-diphenyl-3,4,6,7-tetrahydro2H,6H-benzodipyran-2,6-dione (II) (14percent).This condensation reaction when carried out with resorcinol for 2 hr furnishes 7-hydroxyflavanone (III) (60percent).Condensation of resorcinol monomethyl ether affords 2'-hydroxy-4'-methoxychalcone (IV) (12percent) and 4'-hydroxy-2'-methoxychalcone (V) (40percent), but no flavanone derivative.Reaction of p-methoxycinnamic acid (in xylene), in the presence of PPA and resorcinol, however, yields 7-hydroxy-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin (VI) (56percent); with resorcinol monomethyl ether the corresponding 7-methoxy derivative (VII) (44percent) is obtained.Further, p-methoxycinnamic acid undergoes self-condensation in the presence of 0.5 mol equiv of phloroglucinol or resorcinol to give p-methoxycinnamic anhydride (VIII) (only 4percent) or bis(methoxybenzal)acetone (IX) (50percent).Interestingly, in the presence of resorcinol monomethyl ether (0.5 mol equiv, 4hr) p-methoxycinnamic acid undergoes biogenetic-type oxidative self-cyclisation to form 7-methoxycoumarin (X) (80percent).A plausible mechanism for the formation of X has been suggested.
