1-乙酰基-2-甲基-2,3-二氢喹啉-4-酮 | 128649-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-乙酰基-2-甲基-2,3-二氢喹啉-4-酮
• 英文名称: 1-acetyl-2-methyl-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 1-acetyl-4-oxo-2-methyl-1,2,3,4-tetrahydroquinoline；1-acetyl-2-methyl-2,3-dihydroquinolin-4-one
• CAS: 128649-34-3
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: GRMBWHSWBPDLBU-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  417.1±34.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氟苯胺 、 1-乙酰基-2-甲基-2,3-二氢喹啉-4-酮 在 四氯化钛 ice 、 silica gel 、 乙醚 、 正己烷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以to obtain 1-acetyl-2-methyl-4-[(2-fluorophenyl)imino]-1,2,3,4-tetrahydroquinoline as a yellow oil (60 mg, 81%)的产率得到1-acetyl-2-methyl-4-[(2-fluorophenyl)imino]-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  1-ACYL-4-(PHENOXY, BENZYLOXY, OR PHENYLAMINO)-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES

  摘要：

  本发明涉及一种低分子量化合物，具有促进EPO产生和/或增强血红蛋白表达的活性。具体揭示了一种EPO产生促进剂和/或血红蛋白表达增强剂，包括1-酰基-4-(苯氧基、苄氧基或苯胺基)-1,2,3,4-四氢喹啉衍生物，更具体地，是由通式(1)表示的四氢喹啉化合物；[其中R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或类似物；R4、R5、R6、R7、R8、R9和R16独立地表示氢原子、卤素原子、C1-6烷基或类似物；A表示N—R11或氧原子；R11表示氢原子、C1-6烷基或类似物；n表示0或1]，四氢喹啉化合物的盐或四氢喹啉化合物或其盐的溶剂化物。

  公开号：

  US20130172345A1
• 作为产物：
  描述：

  3-(phenylamino)butanoic acid 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 1-乙酰基-2-甲基-2,3-二氢喹啉-4-酮
  参考文献：
  名称：

  The Discovery of I-BET726 (GSK1324726A), a Potent Tetrahydroquinoline ApoA1 Up-Regulator and Selective BET Bromodomain Inhibitor

  摘要：

  Through their function as epigenetic readers of the histone code, the BET family of bromodomain-containing proteins regulate expression of multiple genes of therapeutic relevance, including those involved in tumor cell growth and inflammation. BET bromodomain inhibitors have profound antiproliferative and anti-inflammatory effects which. translate into efficacy in oncology and inflammation models, and the first compounds have now progressed into clinical trials. The exciting biology of the BETs has led to great interest in the discovery of novel inhibitor classes. Here we describe the identification of a novel tetrahydroquinoline series through up-regulation of apoliproprotein A1 and the optimization into potent compounds active in murine models of septic shock and neuroblastoma. At the molecular level, these effects are produced by inhibiton of BET bromodomains X-rays crystallography reveals the interactions explaining the structure-activity relationships of binding. The resulting lead molecule, I-BET726, represents a new, potent, and selective class of tetrahydroquinoline-based BET inhibitors.

  DOI：

  10.1021/jm5010539

文献信息

• PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR ANEMIA COMPRISING TETRAHYDROQUINOLINE COMPOUND AS ACTIVE INGREDIENT
  申请人：Ashikawa Masanori

  公开号：US20120004197A1

  公开（公告）日：2012-01-05

  Disclosed is a compound which has a low molecular weight and has an activity of enhancing the production of EPO and/or an activity of enhancing the production of hemoglobin. Specifically disclosed is and EPO production enhancer and/or a hemoglobin production enhancer comprising a 1-acyl-4-(substituted oxy, substituted amino, or substituted thio)-1,2,3,4-tetrahydroquinoline derivative, more specifically a tetrahydroquinoline compound represented by general formula (1) [wherein R 1 , R 2 , R 2′ , R 3 and R 3′ independently represent a hydrogen atom, a C 1-6 alkyl group, or the like; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, or the like; A represents N—R 11 , a sulfur atom, or an oxygen atom; R 11 represents a hydrogen atom, a C 1-6 alkyl group, or the like; B represents a C 6-14 aryl group, or a 5- to 10-membered heterocyclic group; and n represents an integer of 0 or 1], a salt of the tetrahydroquinoline compound, or a solvate of the tetrahydroquinoline compound or the salt.

  揭示了一种具有低分子量的化合物，具有增强EPO产生和/或增强血红蛋白产生活性的化合物。具体揭示了一种EPO产生增强剂和/或血红蛋白产生增强剂，包括1-酰基-4-(取代氧基、取代氨基或取代硫基)-1,2,3,4-四氢喹啉衍生物，更具体地说是由通式(1)表示的四氢喹啉化合物【其中R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或类似物；R4、R5、R6、R7、R8、R9和R10独立地表示氢原子、卤素原子、C1-6烷基或类似物；A表示N—R11、硫原子或氧原子；R11表示氢原子、C1-6烷基或类似物；B表示C6-14芳基或5-至10-成员杂环基；n表示0或1的整数】，四氢喹啉化合物的盐，或四氢喹啉化合物或其盐的溶剂化合物。
• PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR ANEMIA, COMPRISING TETRAHYDROQUINOLINE COMPOUND AS ACTIVE INGREDIENT
  申请人：Kowa Company, Ltd.

  公开号：EP2199283A1

  公开（公告）日：2010-06-23

  Disclosed is a low-molecular-weight compound having an EPO production-promoting activity and/or a hemoglobin expression-enhancing activity. Specifically disclosed is an EPO production promoter and/or a hemoglobin expression enhancer comprising a 1-acyl-4-(phenoxy, benzyloxy or phenylamino)-1,2,3,4-tetrahydroquinoline derivative, more specifically a tetrahydroquinoline compound represented by the general formula (1); [wherein R1, R2, R2', R3 and R3' independently represent a hydrogen atom, a C1-6 alkyl group, or the like; R4, R5, R6, R7, R8, R9 and R10 independently represent a hydrogen atom, a halogen atom, a C1-6 alkyl group, or the like; A represents N-R11 or an oxygen atom; R11 represents a hydrogen atom, a C1-6 alkyl group, or the like; and n represents an integer of 0 or 1], a salt of the tetrahydroquinoline compound, or a solvate of the tetrahydroquinoline compound or the salt.

  本文披露了一种具有促进EPO产生活性和/或增强血红蛋白表达活性的低分子化合物。具体披露了一种EPO产生促进剂和/或血红蛋白表达增强剂，包括1-酰基-4-(苯氧基、苄氧基或苯基氨基)-1,2,3,4-四氢喹啉衍生物，更具体地说是由通式（1）表示的四氢喹啉化合物；[其中R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或类似物；R4、R5、R6、R7、R8、R9和R10独立地表示氢原子、卤素原子、C1-6烷基或类似物；A表示N-R11或氧原子；R11表示氢原子、C1-6烷基或类似物；n表示0或1的整数]，四氢喹啉化合物的盐，或四氢喹啉化合物或其盐的溶剂结晶体。
• Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylation
  作者：Bai-Lin Lei、Chang-Hua Ding、Xiao-Fei Yang、Xiao-Long Wan、Xue-Long Hou

  DOI：10.1021/ja9082717

  日期：2009.12.30

  The kinetic resolution of a carbon nucleophile is realized for the first time via Pd-catalyzed asymmetric allylic alkylation with "unstabilized" ketone enolates as the nucleophile, providing both allylated 2,3-disubstituted 2,3-dihydro-4-quinolones and recovered substrates in high yields and high ee (S-factor is 40-145). The application of the methodology in organic synthesis is demonstrated by the

  碳亲核试剂的动力学拆分首次通过 Pd 催化的不对称烯丙基烷基化实现，“不稳定的”酮烯醇化物作为亲核试剂，提供烯丙基化的 2,3-二取代 2,3-二氢-4-喹诺酮和回收的底物高产量和高 ee（S 因子为 40-145）。该方法在有机合成中的应用通过烯丙基化加合物向吡咯并 [3,2-c] 喹啉的快速转化来证明，吡咯并 [3,2-c] 喹啉具有生物活性 Martinella 生物碱的核心结构。
• 1-ACYL-4-(PHENOXY, BENZYLOXY, OR PHENYLAMINO)-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES
  申请人：KOWA COMPANY, LTD.

  公开号：US20130172345A1

  公开（公告）日：2013-07-04

  Disclosed is a low-molecular-weight compound having an EPO production-promoting activity and/or a hemoglobin expression-enhancing activity. Specifically disclosed is an EPO production promoter and/or a hemoglobin expression enhancer comprising a 1-acyl-4-(phenoxy, benzyloxy or phenylamino)-1,2,3,4-tetrahydroquinoline derivative, more specifically a tetrahydroquinoline compound represented by the general formula (1); [wherein R 1 , R 2 , R 2 ′, R 3 and R 3 ′ independently represent a hydrogen atom, a C 1-6 alkyl group, or the like; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 16 independently represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, or the like; A represents N—R 11 or an oxygen atom; R 11 represents a hydrogen atom, a C 1-6 alkyl group, or the like; and n represents an integer of 0 or 1], a salt of the tetrahydroquinoline compound, or a solvate of the tetrahydroquinoline compound or the salt.

  本发明涉及一种低分子量化合物，具有促进EPO产生和/或增强血红蛋白表达的活性。具体揭示了一种EPO产生促进剂和/或血红蛋白表达增强剂，包括1-酰基-4-(苯氧基、苄氧基或苯胺基)-1,2,3,4-四氢喹啉衍生物，更具体地，是由通式(1)表示的四氢喹啉化合物；[其中R1、R2、R2'、R3和R3'独立地表示氢原子、C1-6烷基或类似物；R4、R5、R6、R7、R8、R9和R16独立地表示氢原子、卤素原子、C1-6烷基或类似物；A表示N—R11或氧原子；R11表示氢原子、C1-6烷基或类似物；n表示0或1]，四氢喹啉化合物的盐或四氢喹啉化合物或其盐的溶剂化物。
• US8791090B2
  申请人：——

  公开号：US8791090B2

  公开（公告）日：2014-07-29