1-(1H-咪唑-5-基)-2-甲基丙烷-1-酮 | 247174-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(1H-咪唑-5-基)-2-甲基丙烷-1-酮
• 英文名称: 5-imidazolyl isopropyl ketone
• 英文别名: 1-[1H-imidazol-4(5)-yl]-2-methylpropan-1-one；1-(1H-imidazol-4-yl)-2-methylpropan-1-one；1-(1H-imidazol-4-yl)-2-methyl-1-propanone；1-(1H-imidazol-5-yl)-2-methylpropan-1-one
• CAS: 247174-71-6
• 化学式: C₇H₁₀N₂O
• mdl: MFCD21333142
• 分子量: 138.169
• InChiKey: XFSKTPIUQZQHBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1H-咪唑-5-基)-2-甲基丙烷-1-酮 在 碘 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1-(6-methoxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propan-1-ol
  参考文献：
  名称：

  A Concise Synthesis of Racemic 1-(6,7-Dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol for a Potent C₁₇,₂₀-Lyase Inhibitor

  摘要：

  The development of a practical and scaleable synthesis of 1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol (2) is described. Racemate 2 was synthesized from commercially available 4(5)-imidazolecarboxyaldehyde (7) in three steps excluding chromatography. 4(5)-Cyanoimidazole (10) was prepared from 7 in good yield in a one-pot reaction. A Grignard reaction of cyanoimidazole 10 with isopropylmagnesium bromide followed by the addition of aqueous sulfuric acid formed acylimidazole 9. The final racemate 2 was obtained by the direct Grignard reaction of acylimidazole 9 without N-protection. This process was accomplished efficiently to produce 2 in 70% overall yield from 7 in a large-scale synthesis.

  DOI：

  10.1021/op060171+
• 作为产物：
  描述：

  异丙基溴化镁 、 1H-咪唑-4-甲腈 在 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以82%的产率得到1-(1H-咪唑-5-基)-2-甲基丙烷-1-酮
  参考文献：
  名称：

  A Concise Synthesis of Racemic 1-(6,7-Dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol for a Potent C₁₇,₂₀-Lyase Inhibitor

  摘要：

  The development of a practical and scaleable synthesis of 1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol (2) is described. Racemate 2 was synthesized from commercially available 4(5)-imidazolecarboxyaldehyde (7) in three steps excluding chromatography. 4(5)-Cyanoimidazole (10) was prepared from 7 in good yield in a one-pot reaction. A Grignard reaction of cyanoimidazole 10 with isopropylmagnesium bromide followed by the addition of aqueous sulfuric acid formed acylimidazole 9. The final racemate 2 was obtained by the direct Grignard reaction of acylimidazole 9 without N-protection. This process was accomplished efficiently to produce 2 in 70% overall yield from 7 in a large-scale synthesis.

  DOI：

  10.1021/op060171+

文献信息

• [EN] RAS PROTEIN DEGRADERS, PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC APPLICATIONS<br/>[FR] AGENTS DE DÉGRADATION DE LA PROTÉINE RAS, COMPOSITIONS PHARMACEUTIQUES DE CEUX-CI ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：BIOTHERYX INC

  公开号：WO2021051034A1

  公开（公告）日：2021-03-18

  Provided herein are RAS protein degraders, e.g., a compound of Formula (I), and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventing, or ameliorating one or more symptoms of a RAS-mediated disorder, disease, or condition.

  本文提供了RAS蛋白降解剂，例如化合物式（I）的化合物，以及其药物组合物。本文还提供了它们用于治疗、预防或改善RAS介导的疾病、疾病或症状的方法。
• HEPATITIS C VIRUS INHIBITORS
  申请人：Qiu Yao-Ling

  公开号：US20110064695A1

  公开（公告）日：2011-03-17

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The present invention relates to novel antiviral compounds represented herein above, pharmaceutical compositions comprising such compounds, and methods for the treatment or prophylaxis of viral (particularly HCV) infection in a subject in need of such therapy with said compounds.

  本发明公开了化合物的结构式（I），或其药学上可接受的盐、酯或前药： 这些化合物抑制RNA含病毒，特别是丙型肝炎病毒（HCV）。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并且也可用作抗病毒剂。本发明还涉及包含上述化合物的药物组合物，用于治疗患有HCV感染的受试者。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的HCV感染的方法。本发明涉及上述新型抗病毒化合物，包括含有这些化合物的药物组合物，以及用于治疗或预防受试者需要此类治疗的病毒（特别是HCV）感染的方法。
• Naphthalene derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06573289B1

  公开（公告）日：2003-06-03

  A composition containing a compound of the formula: wherein A is a nitrogen-containing heterocyclic group which may be substituted, R1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R2 is a hydrogen atom or a lower alkyl group which may be substituted, R3, R4, R5, R6, R7, R8 and R9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  包含以下公式化合物的组合物： 其中A是可被取代的含氮杂环基团，R1是氢原子、可被取代的烃基团或可被取代的单环芳族杂环基团，R2是氢原子或可被取代的低级烷基团，R3、R4、R5、R6、R7、R8和R9独立地是氢原子、可被取代的烃基团、可被取代的羟基、可被取代的硫醇基、可被取代的氨基、酰基或卤素原子，其盐或前药对类固醇C17,20-裂解酶具有抑制作用，并且对于例如预防治疗原发恶性肿瘤、其转移和复发等是有用的。
• PROCESS FOR THE PREPARATION OF IMIDAZOLE DERIVATIVES
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1193258A1

  公开（公告）日：2002-04-03

  The present invention provides an industrially advantageous production method of compound (V) having a steroid C17,20 lyase inhibitory action, which affords this compound in a high yield with a less number of steps without using a heavy metal compound: wherein ring A is an optionally substituted imidazole ring, R is an optionally substituted hydrocarbon group or a heterocyclic group, and R1, R2, R3, R4, R5, R6 and R7 are each a hydrogen atom, an optionally substituted hydrocarbon group, OH, SH or NH2, an acyl group or a halogen and the like.

  本发明提供了一种在不使用重金属化合物的情况下，以较少的步骤高产率地制备具有类固醇C17,20裂解酶抑制作用的化合物（V）的工业上有利的生产方法：其中环A是一个可选择取代的咪唑环，R是一个可选择取代的碳氢化合物基团或杂环基团，R1、R2、R3、R4、R5、R6和R7分别是氢原子、可选择取代的碳氢化合物基团、羟基、硫氢基或氨基、酰基或卤素等。
• A Convenient Synthesis of 4(5)-Alkylacyl-1<i>H</i>-imidazoles from 4(5)-Imidazolecarboxaldehyde
  作者：Jun-ichi Kawakami、Kazuhiro Kimura、Masayoshi Yamaoka

  DOI：10.1055/s-2003-38067

  日期：——

  A convenient synthesis of 4(5)-acyl-1H-imidazoles from 4(5)-imidazolecarboxaldehyde without N-protecting group is described. 4(5)-Cyanoimidazole could be synthesized from commercially available 4(5)-imidazolecarboxaldehyde in one-pot. Treatment of 4(5)-cyanoimidazole with various alkylmagnesium bromides followed by addition of aqueous sulfuric acid afforded 4(5)-acyl-1H-imidazoles in good yield.

  描述了一种方便的合成 4(5)-acyl-1H-imidazoles 从 4(5)-imidazolecarboxaldehyde 没有 N-保护基团。4(5)-氰基咪唑可以从市售的4(5)-咪唑甲醛一锅法合成。用各种烷基溴化镁处理 4(5)-氰基咪唑，然后加入硫酸水溶液，以良好的收率得到 4(5)-酰基-1H-咪唑。