178250-12-9Relevant academic research and scientific papers
Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound
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, (2019/08/30)
The invention discloses a fluorinated taxane compound, a preparation method therefor and an application of the fluorinated taxane compound. The compound has a structural general formula represented bya formula I. Proven by pharmacological experiments, compared with paclitaxel, a series of fluorinated taxane derivatives synthesized by the method have cytotoxicity superior to that of the paclitaxelto a multidrug-resistant human mammary cancer cell line MCF-7/Adr and an ovarian cancer cell line NCI/Adr and represent cytotoxicity superior to that of the paclitaxel to a colon cancer cell line HCT-116 with overexpressed neoplasm stem cells.
Design, synthesis and structure-activity relationships of novel taxane-based multidrug resistance reversal agents
Ojima, Iwao,Borella, Christopher P.,Wu, Xinyuan,Bounaud, Pierre-Yves,Oderda, Cecilia Fumero,Sturm, Matthew,Miller, Michael L.,Chakravarty, Subrata,Chen, Jin,Huang, Qing,Pera, Paula,Brooks, Tracy A.,Baer, Maria R.,Bernacki, Ralph J.
, p. 2218 - 2228 (2007/10/03)
A series of novel taxane-based multidrug resistance (MDR) reversal agents (TRAs) has been designed and synthesized. Structure - activity relationship (SAR) study clearly indicates that modification of the C-7 position with hydrophobic arenecarbonylcinnamoyl groups brings about high potency against drug efflux mediated by P-glycoprotein (P-gp). Six TRAs exhibit ability to modulate a wide range of ATP-binding cassette (ABC) transporters, such as P-gp, multidrug resistance-associated protein 1 (MRP1), and breast cancer resistance protein (BCRP), which may serve as novel broad-spectrum modulators of ABC transporters.
Structure-activity relationship study of taxoids for their ability to activate murine macrophages as well as inhibit the growth of macrophage-like cells
Ojima, Iwao,Fumero-Oderda, Cecilia L.,Kuduk, Scott D.,Ma, Zhuping,Kirikae, Fumiko,Kirikae, Teruo
, p. 2867 - 2888 (2007/10/03)
A series of new taxoids modified at the C-3′, C-3′N, C-10, C-2 and C-7 positions has been designed, synthesized and evaluated for their potency to induce NO and TNF production by peritoneal murine macrophages (Mφ) from LPS-responsive C3H/HeN and LPS-hyporesponsive C3H/HeJ strains and human blood cells, and for their ability to inhibit the growth of Mφ-like cell lines J774.1 and J7.DEF3. The SAR-study has shown that the nature of the substituents at these positions have critical effect on the induction of TNF and NO production by Mφ. Positions C-3′ and C-10 are the most flexible and an intriguing effect of the length of the substituents at the C-10 position is observed for taxoids bearing a straight chain alkanoyl moiety. An aromatic group at the C-3′N and C-2 positions is required for the activity, while only hydroxyl or acetyl substituents seem to be tolerated at the C-7 position. The natural stereochemistry in the C-13 isoserine side chain of the taxoids is an absolute requirement for macrophage activation. It has also been clearly shown that there is no correlation between the ability of the taxoids to induce TNF/NO production in C3H/HeN Mφ and the cytotoxicity against Mφ-like cells.
Synthesis and biological evaluation of C-3′NH/C-10 and C-2/C-10 modified paclitaxel analogues
Baloglu, Erkan,Hoch, Jeannine M.,Chatterjee, Sabarni K.,Ravindra, Rudravajhala,Bane, Susan,Kingston, David G. I.
, p. 1557 - 1568 (2007/10/03)
Concurrent modifications on the C-3′NH/C-10, and C-2/C-10 positions on paclitaxel were carried out as a way of investigating possible synergistic effects. The biological activities of these analogues were evaluated in both a microtubule assembly assay and
Syntheses and structure-activity relationships of the second-generation antitumor taxoids: Exceptional activity against drug-resistant cancer cells
Ojima, Iwao,Slater, John C.,Michaud, Evelyne,Kuduk, Scott D.,Bounaud, Pierre-Yves,Vrignaud, Patricia,Bissery, Marie-Christine,Veith, Jean M.,Pera, Paula,Bernacki, Ralph J.
, p. 3889 - 3896 (2007/10/03)
A series of new 3'-(2-methyl-1-propenyl) and 3'-(2-methylpropyl) taxoids with modifications at C-10 was synthesized by means of the β-lactam synthon method using 10-modified 7-(triethylsilyl)-10-deacetylbaccatin III derivatives. The new taxoids thus synth
