111017-07-3Relevant academic research and scientific papers
Design, synthesis, and biological evaluation of new cinnamic derivatives as antituberculosis agents
De, Prithwiraj,Koumba Yoya, Georges,Constant, Patricia,Bedos-Belval, Florence,Duran, Hubert,Saffon, Nathalie,Daffé, Mamadou,Baltas, Michel
experimental part, p. 1449 - 1461 (2011/05/05)
Tuberculosis, HIV coinfection with TB, emergence of multidrug-resistant TB, and extensively drug-resistant TB are the major causes of death from infectious diseases worldwide. Because no new drug has been introduced in the last several decades, new classes of molecules as anti-TB drugs are urgently needed. Herein, we report the synthesis and structure-activity relationships of a series of thioester, amide, hydrazide, and triazolophthalazine derivatives of 4-alkoxy cinnamic acid. Many compounds exhibited submicromolar minimum inhibitory concentrations against Mycobacterium tuberculosis strain (H37Rv). Interestingly, compound 13e, a 4-isopentenyloxycinnamyl triazolophthalazine derivative, was found to be 100-1800 times more active than isoniazid (INH) when tested for its ability to inhibit the growth of INH-resistant M. tuberculosis strains. The results also revealed that 13e does not interfere with mycolic acid biosynthesis, thereby pointing to a different mode of action and representing an attractive lead compound for the development of new anti-TB agents.
Synthesis and anticancer activity evaluation of 2(4-alkoxyphenyl)cyclopropyl hydrazides and triazolo phthalazines
De, Prithwiraj,Baltas, Michel,Lamoral-Theys, Delphine,Bruyère, Céline,Kiss, Robert,Bedos-Belval, Florence,Saffon, Nathalie
experimental part, p. 2537 - 2548 (2010/07/04)
A series of new 2(4-alkoxyphenyl)cyclopropyl hydrazide- and triazolo-derivatives were synthesized starting from 4-hydroxycinnamic acid (1) in a clean, mild, efficient and straightforward synthetic protocol. These compounds consisting of different alkoxy substitution, phenylcyclopropyl backbone and different heterocyclic groups were evaluated for in vitro anticancer activity against 4 cell lines displaying certain levels of resistance to pro-apoptotic stimuli and 2 cell lines sensitive to pro-apoptotic compounds. Compounds 7f and 8e were most active and displaying moderate in vitro cytostatic effect through different mechanisms. Significantly, chemically modified derivatives could be obtained in order to develop novel types of compounds aiming to combat apoptosis-resistant cancers, for example, those cancers associated with dismal prognoses.
In vitro inhibitory activity of boropinic acid against Helicobacter pylori
Epifano, Francesco,Menghini, Luigi,Pagiotti, Rita,Angelini, Paola,Genovese, Salvatore,Curini, Massimo
, p. 5523 - 5525 (2007/10/03)
In this study, we assessed in vitro minimum inhibitory concentration (MIC) values of some natural geranyloxycoumarins, geranyloxy- and isopentenyloxy acids against growth of Helicobacter pylori. Boropinic acid, active principle isolated from Boronia pinnata (Fam. Rutaceae), was seen to be the most effective compound with a MIC value of 1.62 μg/mL.
Megastigmanes and Other Constituents of the Absolute of Boronia megastigma from Tasmania
Weyerstahl, Peter,Marschall, Helga,Bork, Wolf-Rainer,Rilk, Rainer
, p. 1043 - 1048 (2007/10/02)
Some low-volatile constituents of the absolute of Boronia megastigma (Rutaceae) from Tasmania were isolated and characterized.Besides β-ionone (1) and many of its derivatives, e.g. 2-7, we isolated the isomeric 3-hydroxymegastigm-7-en-9-ones 8-10 and the
ORGANIC SYNTHESIS USING HALOBORATION REACTION XVIII. A STEREOSELECTIVE SYNTHESIS OF β-MONO- AND β,β-DISUBSTITUTED α,β-UNSATURATED ESTERS
Yamashina, Naoko,Hyuga, Satoshi,Hara, Shoji,Suzuki, Akira
, p. 6555 - 6558 (2007/10/02)
β-Mono- and β,β-disubstituted α,β-unsaturated esters can be prepared in good yields stereoselectively by the stepwise alkylation and alkoxycarbonylation of 2-bromo-1-alkenylboronates.
