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【结 构 式】 
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【分子编号】21407 【品名】(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoyl chloride 【CA登记号】 |
【 分 子 式 】C20H31ClO 【 分 子 量 】322.91824 【元素组成】C 74.39% H 9.68% Cl 10.98% O 4.95% |
合成路线1
该中间体在本合成路线中的序号：(II)Title compound was prepared by formation of the arachidonic acid chloride (II) upon treatment of the corresponding acid (I) with oxalyl chloride in CH2Cl2 containing DMF at 0 C, followed by condensation with propargylamine (III).
| 【1】 Lin, S.; Khanolkar, A.D.; Fan, P.; Goutopoulos, A.; Qin, C.; Papahadjis, D.; Makriyannis, A.; Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J Med Chem 1998, 41, 27, 5353. |
合成路线2
该中间体在本合成路线中的序号：(II)Title compound was prepared by formation of the arachidonic acid chloride (II) upon treatment of the corresponding acid (I) with oxalyl chloride in CH2Cl2 containing DMF at 0 C, followed by condensation with 2-chloroethylamine - HCl (III) in the presence of pyridine.
| 【1】 Lin, S.; Khanolkar, A.D.; Fan, P.; Goutopoulos, A.; Qin, C.; Papahadjis, D.; Makriyannis, A.; Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. J Med Chem 1998, 41, 27, 5353. |
合成路线3
该中间体在本合成路线中的序号：(II)Treatment of arachidonic acid (I) with oxalyl chloride in benzene containing DMF afforded acid chloride (II), which was then coupled to (R)-2-amino-1-propanol (III) in THF to yield the corresponding arachidonic acid amide.
| 【1】 Abadji, V.; et al.; (R)-Methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability. J Med Chem 1994, 37, 12, 1889. |
合成路线4
该中间体在本合成路线中的序号：(II)Arachidonic acid (I) is converted to the corresponding acid chloride (II) by treatment with oxalyl chloride and DMF. Subsequent condensation of acid chloride (II) with 3-furylmethylamine (III) leads to the desired arachidonic acid amide.
| 【1】 Fernández-Ruiz, J.; Viso, A.; Ortega-Gutiérrez, S.; Ramos, J.A.; González, S.; López-Rodríguez, M.L.; Lastres-Becker, I.; Design, synthesis and biological evaluation of novel arachidonic acis derivatives as highly potent and selective endocannabinoid transporter inhibitors. J Med Chem 2001, 44, 26, 4505. |
| 【2】 Lopez Rodriguez, M.L.; Viso Beronda, A.; Ortega Gutierrez, S.; Latres Becker, I.; Gonzalez Rodriguez de Castro, S.; Fernandez Ruiz, J.J.; Ramos Atance, J.A. (Universidad Complutense de Madrid); Novel araquidonic acid derivs. with affinity toward the anandamide transporter. WO 0212167 . |