- Synthesis and Evaluation of Radioiodinated (E)-18-Iodo-17-octadecenoic Acid as a Model Iodoalkenyl Fatty Acid for Myocardial Imaging
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125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism.This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13).The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes .The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28percent dose/g) with 45percent washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom.Deiodination was low for the first 2 h after injection (2 h, 61percent dose/g).Excellent myocardial images were obtained in a dog with the 123I-labeled agent.
- Knapp, F. F.,Goodman, M. M.,Kabalka, G. W.,Sastry, K. A. R.
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- Ultrasound in fatty acid chemistry: facile dehydrobromination of dibromo fatty esters to acetylenic ester derivatives
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Dehydrobromination of dibromo derivatives of olefinic fatty acids was accomplished using KOH in 20percent aqueous ethanol under cocomitant ultrasonic irradiation (20 kHz) for 30 min at ambient temperature to give the corresponding acetylenic fatty acid derivatives (52-72percent yield).Ten different dibromo fatty acid substrates were used.Products include: fatty acids with a terminal or internal acetylenic bond; acetylenic fatty acids containing an additional functional group, such as hydroxy, chloro or azide group.The structures of the products were characterized by infrared and NMR spectroscopy. - Keywords: acetylenic fatty esters; dehydrobromination; dibromo fatty esters; ultrasond
- Jie, Marcel S. F. Lie Ken,Kalluri, P.
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- Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling of N-Fluorinated Sulfonimides with Simple Alkynes
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The facile synthesis of aminoallenes, accomplished by a selenium-π-acid-catalyzed cross-coupling of an N-fluorinated sulfonimide with simple, non-activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre-activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. The operating reaction conditions tolerate numerous functional groups such as esters, nitriles, (silyl)ethers, acetals, and halogen substituents, furnishing the target compounds in up to 86 % yield.
- Rode, Katharina,Ramadas Narasimhamurthy, Poorva,Rieger, Rene,Kr?tzschmar, Felix,Breder, Alexander
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supporting information
p. 1720 - 1725
(2021/03/16)
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- Efficient synthesis of unsaturated 1-monoacyl glycerols for in meso crystallization of membrane proteins
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A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization. Georg Thieme Verlag Stuttgart.
- Fu, Yu,Weng, Yue,Hong, Wen-Xu,Zhang, Qinghai
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p. 809 - 812
(2011/06/21)
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- NITROSOCHLORINATION OF ACETYLENIC FATTY ACID ESTERS
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Nitrosochlorination of methyl 9-octadecynoate (I) and methyl 9-undecynoate (II) with nitrosyl chloride gas (NOCl) furnishes eutectic mixtures of vinyl chloronitroso adducts (IV) and (V) in moderate yields while methyl 10-undecynoate (III) affords a vinyl chloronitroso adduct (VIa) and a vinyl chlorohydroxy derivative (VII), a rearranged product.
- Siddiqui, Mansoor M.,Ahmad, Fasih,Osman, Sheikh M.
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p. 1801 - 1814
(2007/10/02)
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