78119-19-4Relevant 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 chemical transformations of 4-hexadecyloxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane
Malekin,Khromova,Kisin,Kruglyak,Kurochkin
, p. 677 - 682 (2007/10/03)
Cyclophosphorylation of 1-hexadecylglycerol with phosphorus oxychloride afforded 4-hexadecyl-oxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane (I) with high yield. By means of 1H, 13C, and 31P NMR, it was shown to be a 1 : 9 mixture of two stable epimers with equatorial and axial configuration of the chlorine atom, respectively. Phospholane (I) entered into nucleophilic reactions with KHCO3 and HN(Pri)2 to give 80-85% yields of the chlorine substitution products with the phospholane cycle remaining intact. Interaction of the phospholane (I) with water or choline tosylate also initially produced substituted phospholanes, as shown by NMR. Subsequent hydrolysis led to the cleavage of the phospholane ring and to formation of isomeric 1-hexadecylglycero-2- and 3-phosphates and 1-hexadecylglycero-2- and 3-phosphocholines, respectively. A method for the separation of isomeric phosphates was developed, which made it possible to isolate 1-hexadecylglycero-2-phosphate and 1-hexadecylglycero-3-phosphate.
Influence of α-branched fatty acid chains on the thermotropic behaviour of racemic 1-O-hexadecyl-2-acyl-glycero-3-phosphocholines
Rattay, Bernd,Brezesinski, Gerald,Dobner, Bodo,Foerster, Guenter,Nuhn, Peter
, p. 81 - 92 (2007/10/02)
Phosphatidylcholines containing an α-branched palmitic acid ester linked to position C2 of the glycerol backbone were synthesized and characterized using differential scanning calorimetry and X-ray diffraction. As the length of the sidegroup substituted on the palmitic acid chain is changed, the calorimetric parameters pass through a minimum. The polymorphic behaviour is different when the sidegroup is larger, or smaller, than propyl. The comparison of the physicochemical parameters of isomers differing in the bonding of the branched chain fatty acid to the glycerol backbone (to position C1 or C2, respectively) shows that the chains are nonequivalent. Keywords: Phosphatidylcholine; Branched chain fatty acids; Microcalorimetry; X-ray diffraction; Polymorphism
NOVEL ENANTIOSELECTIVE SYNTHESIS OF PLATELET ACTIVATING FACTOR AND ITS ENANTIOMER VIA RING OPENING OF GLYCIDYL TOSYLATE WITH 1-HEXADECANOL
Guivisdalsky, Pedro N.,Bittman, Robert
, p. 4393 - 4396 (2007/10/02)
(2R)-and(2S)-Glycidyl tosylates 3 and 3' were used to synthesize platelet activating factor 1 and its enantiomer 2 in very high optical purity via the ring-opened ether-linked glycerol tosylate 4 and 4'
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
