34240-68-1Relevant academic research and scientific papers
Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids
Alam, Md. Maqusood,Hassan, Ahmed H.E.,Lee, Kun Won,Cho, Min Chang,Yang, Ji Seul,Song, Jiho,Min, Kyung Hoon,Hong, Jongki,Kim, Dong-Hyun,Lee, Yong Sup
, p. 51 - 62 (2018/11/27)
Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.
Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs
Pedersen, Palle J.,Christensen, Mikkel S.,Ruysschaert, Tristan,Linderoth, Lars,Andresen, Thomas L.,Melander, Fredrik,Mouritsen, Ole G.,Madsen, Robert,Clausen, Mads H.
supporting information; experimental part, p. 3408 - 3415 (2010/03/31)
The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol he
Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue
Andresen, Thomas L.,Jensen, Simon S.,Madsen, Robert,J?rgensen, Kent
, p. 7305 - 7314 (2007/10/03)
The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinicall
Formation of a Structural Isomer of Platelet Activating Factor on the Acetylation of 1-Alkyl-sn-Glycero-3-Phosphocholines
Chupin, V. V.,Ostanenko, O. V.,Klykov, V. N.,Anikin, M. V.,Serebrennikova, G. A.
, p. 667 - 674 (2007/10/02)
The key stage in the synthesis of the platelet activating factor (PAT) - the acetylation of 1-alkyl-sn-glycero-3-phosphocholines (lyso-PAT) with acetic anhydride - has been studied.The formation of a structural isomer of PAT - 1-alkyl-3-acetyl-sn-glycero-3-phosphocholines - as a by-product when the reaction is carried out in the presence of bases (triethylamine, 4-dimethylaminopyridine) has been shown.Acetylation under the conditions of acid catalysis gave the isomerically pure PAT.The mechanism of the reaction leading to the formation of the PAT isomer is discussed.
Optically active oxiranes. Synthesis of PAF (Platelet Aggregating Factor)
Cimetiere, B,Jacob, L,Julia, M
, p. 926 - 938 (2007/10/02)
A number of epoxides bearing no function in the α-position have been converted into β-hydroxy sulfonium salts.Association with an otically active acid (dibenzoyltartaric) allowed the resolution.This method has been used to prepare the optically active glycidol octadecyl ether which was converted into (-) PAF. Key words: oxiranes / resolution / PAF synthesis
An efficient synthesis of Platelet-Activating Factor (PAF) via 1-o-alkyl-2-o-(3-isoxazolyl)-SN-glycero-3-phosphocholine, a new PAF agonist utilization of the 3-isoxazolyloxy group as a protected hydroxyl
Nakamura, Norio,Miyazaki, Hideki,Ohkawa, Nobuyuki,Oshima, Takeshi,Koike, Hiroyuki
, p. 699 - 702 (2007/10/02)
Potent PAF agonists (R)-3a,b were synthesized and converted into PAF. Key steps include Mitsunobu reaction of a chiral secondary alcohol with 3-hydroxyisoxazole as the acidic component, and hydrogenolytic ring cleavage of the resulting 3-isoxazolyloxy gro
Structure-Activity Relationship in PAF-acether. 3. Hydrophobic Contribution to Agonistic Activity
Godfroid, Jean-Jacques,Broquet, Colette,Jouquey, Simone,Lebbar, Mariya,Heymans, Francoise,et al.
, p. 792 - 797 (2007/10/02)
The synthesis of some selected PAF-acether homologues with an alkoxy-chain length from C1 to C20 in position 1 is described.All agonist activities are closely correlated among themselves and with the calculated fatty-chain hydrophobicity.After a discussio
RESOLUTION OF OXIRANES. APPLICATION TO THE SYNTHESIS OF THE PLATELET AGGREGATION FACTOR
Cimetiere, Bernard,Jacob, Laurent,Julia, Marc
, p. 6329 - 6332 (2007/10/02)
Resolution of racemic oxiranes has been achieved through their conversion into hydroxy sulfonium salts of dibenzoyltartaric acid.Thus, resolution of n-octadecyl glycidyl ether followed by reaction with phosphorylcholine and acetylation led to C18-P.A.F.
Method of use of 1-(alkyl for alkylcarbanoyl)-2-carbamoylglycerol derivatives
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, (2008/06/13)
Glycerol derivatives, inclusive of salts thereof, of the formula STR1 wherein R1 is alkyl or alkylcarbamoyl containing 10 to 30 carbon atoms, R2 and R3 are independently hydrogen, C1-6 alkyl or, taken together w
