119944-30-8Relevant academic research and scientific papers
Syntheses of L‐rhamnose‐linked amino glycerolipids and their cytotoxic activities against human cancer cells
Arthur, Gilbert,Idowu, Temilolu,Nachtigal, Mark,Ogunsina, Makanjuola,Samadder, Pranati,Schweizer, Frank
, (2020/02/06)
A major impediment to successful cancer treatment is the inability of clinically available drugs to kill drug‐resistant cancer cells. We recently identified metabolically stable L‐glucosaminebased glycosylated antitumor ether lipids (GAELs) that were cytotoxic to chemotherapy‐resistant cancer cells. In the absence of commercially available L‐glucosamine, many steps were needed to synthesize the compound and the overall yield was poor. To overcome this limitation, a facile synthetic procedure using commercially available L‐sugars including L‐rhamnose and L‐glucose were developed and the L‐GAELs tested for anticancer activity. The most potent analog synthesized, 3‐amino‐1‐O‐hexadecyloxy‐2R‐(O–α‐L‐rhamnopyranosyl)‐sn‐ glycerol 3, demonstrated a potent antitumor effect against human cancer cell lines derived from breast, prostate, and pancreas. The activity observed was superior to that observed with clinical anticancer agents including cisplatin and chlorambucil. Moreover, like other GAELs, 3 induced cell death by a non‐membranolytic caspase‐independent pathway.
Isosteric phosphonate analogs of ET-16-OMe. Synthesis and biological evaluation of the enantiomers of 2'-(trimethylammonio)ethyl 4-(hexadecyloxy)- 3-methoxybutanephosphonate and 2'-(trimethylammonio)ethyl 4-(hexadecylthio)- 3-methoxybutanephosphonate
Bittman,Byun,Mercier,Salari
, p. 425 - 430 (2007/10/02)
The enantiomers of two isosteric phosphonate analogs of the ether-linked antitumor agent 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (ET-18- OMe) were synthesized and evaluated for their cytotoxicity against various mouse leukemic cell lines in v
Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids
Guivisdalsky, Pedro N.,Bittman, Robert
, p. 4637 - 4642 (2007/10/02)
A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio- and stereospecific nucleophilic opening of the p-toluenesulfonate (1a, 1b) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)- or (S)-glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst.The enantiomeric excess of the ring-opened products was >94percent, as judged by 1H NMR and chiral HPLC analysis of the Mosher ester derivatives, indicating that ring opening of 1 and 6 proceeds without significant loss of optical purity.The synthetic strategy of using optically active glycidyl derivatives as the precursor of the glycerol backbone permits the desired enantiomers of 1(3)-O-2-O-methylphosphocholines (5a, 5b) to be generated in good yield and high optical purity from the ring-opened intermediates (2, 7) in three steps without the use of protecting groups.
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'
