1-戊基-5-(羟甲基)咪唑 | 226930-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-戊基-5-(羟甲基)咪唑
• 英文名称: 1-pentyl-5-(hydroxymethyl)imidazole
• 英文别名: 5-Hydroxymethyl-1-pentylimidazole；(3-Pentylimidazol-4-yl)methanol
• CAS: 226930-92-3
• 化学式: C₉H₁₆N₂O
• 分子量: 168.239
• InChiKey: CJXGWUPSGLRIRD-UHFFFAOYSA-N

物化性质

• 沸点：
  346.0±17.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-戊基-5-(羟甲基)咪唑 在 manganase dioxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 4-[N-(1-pentyl-1H-imidazol-5-yl)methylamino]-2-phenylbenzoylmethionine methyl ester
  参考文献：
  名称：

  Design and Synthesis of Peptidomimetic Protein Farnesyltransferase Inhibitors as Anti-Trypanosoma brucei Agents

  摘要：

  On the basis of the structure of the CVIM tetrapeptide substrate of mammalian protein farnesyltransferase, a series of imidazole-containing peptidomimetics was designed and synthesized, and their inhibition activity against Trypanosoma brucel protein farnesyltransferase (TbPFT) was evaluated. Peptidomimetics where the 5-position of the imidazole ring was linked to the hydrophobic scaffold showed over 70% inhibition activity at 50 nM in the enzyme assay, whereas the corresponding C-4 regioisomers were less potent. The ester prodrug 23 was found to be a potent inhibitor against cultured Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense cells with ED50 values of 0.025 and 0.0026 muM, respectively. Furthermore introducing a second imidazole group into 23 led to 31, which showed the highest inhibition activity against the parasite with an ED50 of 0.0015 muM. The potency of the TbPFT inhibitors and the cytotoxicity of the corresponding esters to T. brucei cells were shown to be highly correlated. These studies validate TbPFT as a target for the development of novel therapeutics against African sleeping sickness.

  DOI：

  10.1021/jm030236o
• 作为产物：
  描述：

  1-溴戊烷 、 4-羟甲基咪唑盐酸盐 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以8%的产率得到1-戊基-5-(羟甲基)咪唑
  参考文献：
  名称：

  Design and Synthesis of Peptidomimetic Protein Farnesyltransferase Inhibitors as Anti-Trypanosoma brucei Agents

  摘要：

  On the basis of the structure of the CVIM tetrapeptide substrate of mammalian protein farnesyltransferase, a series of imidazole-containing peptidomimetics was designed and synthesized, and their inhibition activity against Trypanosoma brucel protein farnesyltransferase (TbPFT) was evaluated. Peptidomimetics where the 5-position of the imidazole ring was linked to the hydrophobic scaffold showed over 70% inhibition activity at 50 nM in the enzyme assay, whereas the corresponding C-4 regioisomers were less potent. The ester prodrug 23 was found to be a potent inhibitor against cultured Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense cells with ED50 values of 0.025 and 0.0026 muM, respectively. Furthermore introducing a second imidazole group into 23 led to 31, which showed the highest inhibition activity against the parasite with an ED50 of 0.0015 muM. The potency of the TbPFT inhibitors and the cytotoxicity of the corresponding esters to T. brucei cells were shown to be highly correlated. These studies validate TbPFT as a target for the development of novel therapeutics against African sleeping sickness.

  DOI：

  10.1021/jm030236o

文献信息

• Imidazole derivatives having an inhibitory activity for farnesyl transferase and process for preparation thereof
  申请人：LG Chemical Ltd.

  公开号：US06268363B1

  公开（公告）日：2001-07-31

  The present invention relates to a novel imidazole derivative represented by formula (1) which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts or isomers thereof, in which A, n1 and Y are defined in the specification; to a process for preparation of the compound of formula (1); to intermediates which are used in the preparation of the compound of formula (1); and to a pharmaceutical composition comprising the compound of formula (1) as an active ingredient.

  本发明涉及一种新型咪唑衍生物，其化学式表示为（1），该化合物对法尼基转移酶具有抑制活性，或者其药学上可接受的盐或同分异构体，其中A、n1和Y在规范中有定义；制备化合物（1）的方法；用于制备化合物（1）的中间体；以及包含化合物（1）作为活性成分的药物组合物。
• [EN] IMIDAZOLE DERIVATIVES HAVING AN INHIBITORY ACTIVITY FOR FARNESYL TRANSFERASE AND PROCESS FOR PREPARATION THEREOF<br/>[FR] DERIVES D'IMIDAZOLE A ACTIVITE INHIBITRICE DE FARNESYLE TRANSFERASE ET LEUR PROCEDE DE PREPARATION
  申请人：LG CHEMICAL LTD.

  公开号：WO1999028315A1

  公开（公告）日：1999-06-10

  (EN) The present invention relates to a novel imidazole derivative represented by formula (1) which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts or isomers thereof, in which A, n1 and Y are defined in the specification; to a process for preparation of the compound of formula (1); to intermediates which are used in the preparation of the compound of formula (1); and to a pharmaceutical composition comprising the compound of formula (1) as an active ingredient.(FR) La présente invention concerne un nouveau dérivé d'imidazole représenté par la formule (1) présentant une activité inhibitrice contre la farnésyle transférase, ou ses sels ou isomères acceptables sur le plan pharmaceutique, formule dans laquelle A, n1 et Y sont définis dans le description de l'invention; un procédé de préparation du composé de la formule (1); des intermédiaires utilisés dans la préparation du composé de la formule (1); et une composition pharmaceutique comprenant le composé de la formule (1) en tant que principe actif.

  (中) 本发明涉及一种新的咪唑衍生物，其表示为式（1），该衍生物对法尼酰转移酶具有抑制活性，或其药学上可接受的盐或异构体，其中A、n1和Y在规范中定义；制备式（1）化合物的方法；用于制备式（1）化合物的中间体；以及包含式（1）化合物作为活性成分的药物组合物。
• IMIDAZOLE DERIVATIVES HAVING AN INHIBITORY ACTIVITY FOR FARNESYL TRANSFERASE AND PROCESS FOR PREPARATION THEREOF
  申请人：LG CHEMICAL LIMITED

  公开号：EP1045846B1

  公开（公告）日：2003-05-02
• US6268363B1
  申请人：——

  公开号：US6268363B1

  公开（公告）日：2001-07-31
• US6472526B1
  申请人：——

  公开号：US6472526B1

  公开（公告）日：2002-10-29