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【结 构 式】 
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【分子编号】21406 【品名】(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid 【CA登记号】7771-44-0 |
【 分 子 式 】C20H32O2 【 分 子 量 】304.47288 【元素组成】C 78.9% H 10.59% O 10.51% |
合成路线1
该中间体在本合成路线中的序号：(I)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：(I)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：(I)Arachidonic acid (I) was converted to the mixed anhydride (II) upon treatment with isobutyl chloroformate and triethylamine. Subsequent condensation of (II) with 2-chloroethylamine (III) provided the target amide.
| 【1】 Murphy, V.; Greenberg, M.J.; Manna, S.; Dicamelli, R.; Ross, R.A.; Campbell, W.B.; Stevenson, L.A.; Hillard, C.J.; Pertwee, R.G.; Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J Pharmacol Exp Ther 1999, 289, 3, 1427. |
合成路线4
该中间体在本合成路线中的序号：(I)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5
该中间体在本合成路线中的序号：(I)Curtius rearrangement of arachidonic acid (I) in the presence of diphenyl phosphoryl azide in hot benzene gave isocyanate (II), which was coupled with methylamine to yield the title urea.
| 【1】 Aung, M.M.; Abood, M.E.; Martin, B.R.; Razdan, R.K.; Ng, E.W.; Unique analogues of anandamide: Arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas. J Med Chem 1999, 42, 1975. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 11021 | Methanamine; Methylamine | 74-89-5 | CH5N | 详情 | 详情 | |
| (I) | 21406 | (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid | 7771-44-0 | C20H32O2 | 详情 | 详情 |
| (II) | 26237 | (4Z,7Z,10Z,13Z)-1-isocyanato-4,7,10,13-nonadecatetraene; (4Z,7Z,10Z,13Z)-4,7,10,13-nonadecatetraenyl isocyanate | C20H31NO | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(I)Curtius rearrangement of arachidonic acid (I) in the presence of diphenyl phosphoryl azide in hot benzene gave isocyanate (II), which was coupled with 2-fluoroethylamine (III) to yield the title urea.
| 【1】 Aung, M.M.; Abood, M.E.; Martin, B.R.; Razdan, R.K.; Ng, E.W.; Unique analogues of anandamide: Arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas. J Med Chem 1999, 42, 1975. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 21406 | (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid | 7771-44-0 | C20H32O2 | 详情 | 详情 |
| (II) | 26237 | (4Z,7Z,10Z,13Z)-1-isocyanato-4,7,10,13-nonadecatetraene; (4Z,7Z,10Z,13Z)-4,7,10,13-nonadecatetraenyl isocyanate | C20H31NO | 详情 | 详情 | |
| (III) | 26238 | 3-fluoro-1-propanamine; 3-fluoropropylamine | C3H8FN | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(I)Curtius rearrangement of arachidonic acid (I) in the presence of diphenyl phosphoryl azide in hot benzene gave isocyanate (II), which was coupled with ethanolamine (III) to yield the title urea.
| 【1】 Aung, M.M.; Abood, M.E.; Martin, B.R.; Razdan, R.K.; Ng, E.W.; Unique analogues of anandamide: Arachidonyl ethers and carbamates and norarachidonyl carbamates and ureas. J Med Chem 1999, 42, 1975. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 21406 | (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acid | 7771-44-0 | C20H32O2 | 详情 | 详情 |
| (II) | 26237 | (4Z,7Z,10Z,13Z)-1-isocyanato-4,7,10,13-nonadecatetraene; (4Z,7Z,10Z,13Z)-4,7,10,13-nonadecatetraenyl isocyanate | C20H31NO | 详情 | 详情 | |
| (III) | 18522 | 3-amino-1-propanol | 156-87-6 | C3H9NO | 详情 | 详情 |
合成路线8
该中间体在本合成路线中的序号：(I)Arachidonic acid (I) was converted to the mixed anhydride (II) upon treatment with isobutyl chloroformate and triethylamine. Subsequent condensation of (II) with cyclopropylamine (III) provided the target amide.
| 【1】 Murphy, V.; Greenberg, M.J.; Manna, S.; Dicamelli, R.; Ross, R.A.; Campbell, W.B.; Stevenson, L.A.; Hillard, C.J.; Pertwee, R.G.; Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J Pharmacol Exp Ther 1999, 289, 3, 1427. |
合成路线9
该中间体在本合成路线中的序号：(I)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 . |