ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-β-D-glycero-pentofuranosyl)imidazole-1-carboxylate | 252054-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-β-D-glycero-pentofuranosyl)imidazole-1-carboxylate
• 英文别名: ethyl 4-[(2R,5S)-5-phthaloylaminotetrahydrofuran-2-yl]imidazole-1-carboxylate；ethyl 4-[(2R,5S)-5-[(1,3-dioxoisoindol-2-yl)methyl]oxolan-2-yl]imidazole-1-carboxylate
• CAS: 252054-28-7
• 化学式: C₁₉H₁₉N₃O₅
• 分子量: 369.377
• InChiKey: PMBKSOSAQCQVBX-BLLLJJGKSA-N

物化性质

• 沸点：
  556.5±60.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  90.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-β-D-glycero-pentofuranosyl)imidazole-1-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以85%的产率得到(+)-4(5)-[(2R,5S)-(5-aminomethyl)tetrahydrofuran-2-yl]imidazole
  参考文献：
  名称：

  Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl- or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficient Use of a PhSe Group:  Application to Novel Histamine H₃-Ligands¹

  摘要：

  将以下文本翻译成中文： (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose. --- (+)-4(5)-[(2R,5S)-(5-氨基甲基)四氢糠基-2-基]咪唑 1 与其 C2' 异构体 (-)-2，作为新型咪唑 C-核苷的 5'-氨基衍生物，通过 beta- 和 alpha-2'-苯基硒基核苷 15 和 16 合成。15 和 16 这种异构体通过一种新型 C-核苷合成方法制得，从 L-谷氨酸出发，通过二醇中间体 12 和 14 消除 PhSeCl 并进行硒环化反应。其 ent-1 和 ent-2（咪吗啡啉），其中后者被确认为一种新型组胺 H-3 �受体激动剂，通过体内脑微透析方法验证，也由此从 D-谷氨酸制得。此外，通过关键中间体（15、16、ent-15 和 ent-16）中 PhSe 基团的氧化消除，合成了 4(5)-[(5-氨基甲基)-2,5-二氢糠基-2-基]咪唑的四种异构体（3、4、ent-3 和 ent-4）。与本研究相关，4(5)-(5-氨基甲基糠基-2-基)-1H-咪唑 (5) 也从 D-核糖开始制得。

  DOI：

  10.1021/jo9910637
• 作为产物：
  描述：

  ethyl 4-(5-O-benzyl-2,3-dideoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl)imidazole-1-carboxylate 在 palladium dihydroxide 三乙基硼 、 偶氮二甲酸二异丙酯 、 三正丁基氢锡 、 环己烯 、 4-(二甲氨基)三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 20.5h， 生成 ethyl 4-(5-phthaloylamino-2,3,5-trideoxy-β-D-glycero-pentofuranosyl)imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl- or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficient Use of a PhSe Group:  Application to Novel Histamine H₃-Ligands¹

  摘要：

  将以下文本翻译成中文： (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose. --- (+)-4(5)-[(2R,5S)-(5-氨基甲基)四氢糠基-2-基]咪唑 1 与其 C2' 异构体 (-)-2，作为新型咪唑 C-核苷的 5'-氨基衍生物，通过 beta- 和 alpha-2'-苯基硒基核苷 15 和 16 合成。15 和 16 这种异构体通过一种新型 C-核苷合成方法制得，从 L-谷氨酸出发，通过二醇中间体 12 和 14 消除 PhSeCl 并进行硒环化反应。其 ent-1 和 ent-2（咪吗啡啉），其中后者被确认为一种新型组胺 H-3 �受体激动剂，通过体内脑微透析方法验证，也由此从 D-谷氨酸制得。此外，通过关键中间体（15、16、ent-15 和 ent-16）中 PhSe 基团的氧化消除，合成了 4(5)-[(5-氨基甲基)-2,5-二氢糠基-2-基]咪唑的四种异构体（3、4、ent-3 和 ent-4）。与本研究相关，4(5)-(5-氨基甲基糠基-2-基)-1H-咪唑 (5) 也从 D-核糖开始制得。

  DOI：

  10.1021/jo9910637

文献信息

• Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl- or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficient Use of a PhSe Group:  Application to Novel Histamine H₃-Ligands¹
  作者：Shinya Harusawa、Tomonari Imazu、Seiichiroh Takashima、Lisa Araki、Hirofumi Ohishi、Takushi Kurihara、Yasuhiko Sakamoto、Yumiko Yamamoto、Atsushi Yamatodani

  DOI：10.1021/jo9910637

  日期：1999.11.1

  (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of-the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose.

  将以下文本翻译成中文： (+)-4(5)-[(2R,5S)-(5-Aminomethyl)tetrahydrofuran-2-yl]imidazole 1 and its C2' epimer (-)-2, which are the 5'-amino derivatives of a novel imidazole C-nucleoside, were synthesized via beta- and alpha-2'-phenylselenenyl nucleosides 15 and 16. The anomers 15 and 16 were provided by a new synthetic method for C-nucleosides via the elimination of PhSeCl and selenocyclization from diol intermediates 12 and 14, starting from L-glutamic acid. Their ent-1 and ent-2 (imifuramine), the latter of which was indicated as a novel type of histamine H-3-agonist confirmed by an in vivo brain microdialysis method, were synthesized by the same methodology from D-glutamic acid. The four isomers (3, 4, ent-3, and ent-4) of a 4(5)-[(5-aminomethyl)-2,5-dihydrofuran-2-yl]imidazole were also synthesized via the oxidative elimination of the PhSe group of the key intermediates (15, 16, ent-15, and ent-16). In connection with this study, 4(5)-(5-aminomethylfuran-2-yl)-1H-imidazole (5) was also synthesized starting from D-ribose. --- (+)-4(5)-[(2R,5S)-(5-氨基甲基)四氢糠基-2-基]咪唑 1 与其 C2' 异构体 (-)-2，作为新型咪唑 C-核苷的 5'-氨基衍生物，通过 beta- 和 alpha-2'-苯基硒基核苷 15 和 16 合成。15 和 16 这种异构体通过一种新型 C-核苷合成方法制得，从 L-谷氨酸出发，通过二醇中间体 12 和 14 消除 PhSeCl 并进行硒环化反应。其 ent-1 和 ent-2（咪吗啡啉），其中后者被确认为一种新型组胺 H-3 �受体激动剂，通过体内脑微透析方法验证，也由此从 D-谷氨酸制得。此外，通过关键中间体（15、16、ent-15 和 ent-16）中 PhSe 基团的氧化消除，合成了 4(5)-[(5-氨基甲基)-2,5-二氢糠基-2-基]咪唑的四种异构体（3、4、ent-3 和 ent-4）。与本研究相关，4(5)-(5-氨基甲基糠基-2-基)-1H-咪唑 (5) 也从 D-核糖开始制得。
• Efficient Synthesis of trans- or cis-4(5)-(5-Aminomethyltetrahydrofuran-2-yl)imidazoles via Diazafulvene Intermediates: Synthetic Approach toward Human Histamine H4-Ligands
  作者：Shinya Harusawa、Lisa Araki、Hirotaka Terashima、Makoto Kawamura、Seiichiro Takashima、Yasuhiko Sakamoto、Takeshi Hashimoto、Yumiko Yamamoto、Atsushi Yamatodani、Takushi Kurihara

  DOI：10.1248/cpb.51.832

  日期：——

  unsubstituted imidazole moiety in good yields. This methodology also afforded an alternative synthetic route to trans- and cis-ethyl 4(5)-(5-hydroxymethyltetrahydrofuran-2-yl)imidazole carboxylates (5 and 6), reported previously. Also, 4(5)-[(2R,5S)-5-aminomethyltetrahydrofuran-2-yl]imidazole (+)-2 was synthesized from ethyl 4(5)-(2-deoxy-beta-D-ribofuranosyl)imidazole-1-carboxylate (35) via the four steps involving

  预期（+）-4（5）-[（2R，5R）-5-氨基甲基四氢呋喃-2-基]咪唑[（+）-1，imifuramine]及其2R，5S-立体异构体（+）-2为碱化合物以开发选择性的人类组胺H4受体配体。（+）-1的改进合成是通过将Bu3P / N，N，N'，N'-四甲基偶氮二甲酰胺（TMAD）处理带有未取代咪唑部分的二醇17ab生成的二氮烯富烯中间体进行环化来完成的。这种方法还提供了另一种合成途径，可以合成先前报道的4（5）-（5-羟甲基四氢呋喃-2-基）咪唑羧酸酯的反式和顺式（5和6）。另外，由乙基4（5）-（2-脱氧-β-D-核呋喃呋喃糖基）咪唑-乙基合成了4（5）-[（（2R，5S）-5-氨基甲基四氢呋喃-2-基]咪唑（+）-2。通过涉及脱氧的四个步骤使1-羧酸盐（35）。