112638-50-3Relevant academic research and scientific papers
The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogs: An improved procedure for the synthesis of the key synthon methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate
Dasse, Olivier,Mahadevan, Anu,Han, Luning,Martin, Billy R.,Marzo, Vincenzo Di,Razdan, Raj K.
, p. 9195 - 9202 (2000)
Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to t
SYNTHESIS OF THREE NEW DEHYDROARACHIDONIC ACID DERIVATIVES AND THEIR OXIDATION BY SOYBEAN LIPOXYGENASE
Corey, E. J.,Nagata, Ryu
, p. 5391 - 5394 (1987)
The synthesis of dehydroarachidonic acid derivatives 1-3 is descriebed together with their oxidation by soybean lipoxygenase.The results of these and kinetic studies suggest the occurence of organoiron intermediates in lipoxygenation.
Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium
Nanba, Yutaro,Shinohara, Riku,Morita, Masao,Kobayashi, Yuichi
supporting information, p. 8614 - 8626 (2017/10/27)
The reaction of TMS-substituted epoxy alcohols (and derivatives) with dimsyl sodium (NaDMSO) to give 1-alkene-3,4-diols was used for the synthesis of enantiomerically enriched 17(R),18(S)-EpETE and two diastereoisomers of isoleukotoxin diol. In the synthesis of 17(R),18(S)-EpETE, the α-ethoxyethyl ether (EE) of the epoxy alcohol derived from (R)-1-TMS-1-penten-3-ol underwent reaction with NaDMSO to give the mono EE-protected 1-hexene-3,4-diol. The aldehyde obtained by hydroboration/oxidation was subjected to Wittig reaction to afford a mono EE-protected diol. The corresponding mono mesylate was prepared and subjected to epoxide ring formation to afford 17(R),18(S)-EpETE stereoselectively. Similarly, a reaction of the anti epoxy alcohol derived from (R)-1-TMS-1-octen-3-ol with NaDMSO gave the anti form of 1-nonene-3,4-diol, which was converted to 12(S),13(R)-isoleukotoxin diol through Wittig reaction. 12(R),13(R)-Isoleukotoxin diol was synthesized in a similar manner.
9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma
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Page/Page column 7-8, (2010/11/30)
9,11-Cycloendoperoxide derivatives of biologically active prostaglandin analogs, and particularly of the ocular hypotensive drugs Bimatoprost, Latanaprost, Unoprostone, Travoprost and prostaglandin H2 1-ethanolamide or of structurally closely related analogs, are pro-drugs which hydrolyze under physiological conditions to provide prostaglandin analogues that are capable of providing sustained ocular and other in vivo concentrations of the respective drugs. The compounds of the invention have the formula shown below where the variables have the meaning defined in the specification.
