2,3-二氢-2-甲基-4(1h)-喹啉酮 | 30448-37-4

• 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: 2,3-二氢-2-甲基-4(1h)-喹啉酮
• 中文别名: 2,3-二氢-2-甲基-4(1H)-喹啉酮
• 英文名称: 2-methyl-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 2-methyl-2,3-dihydro-1H-quinolin-4-one；1,2,3,4-tetrahydro-2-methyl-4-quinolinone；2-methyl-2,3-dihydro-4(1H)-quinolinone；2-methyl-2,3-dihydro-1H-quinolin-4-one
• CAS: 30448-37-4
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: KTJXYZFZRRYVJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  301.4±22.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2,3-二氢-2-甲基-4(1h)-喹啉酮 在 potassium carbonate 、 钯 、 顺丁烯二酸 作用下， 生成 4-羟基-2-甲基喹啉
  参考文献：
  名称：

  Preparation of 4-hydroxyquinoline compounds

  摘要：

  公开号：

  US02558211A1
• 作为产物：
  描述：

  苯胺 在 polyphosphoric acid 作用下， 以 甲苯 为溶剂， 反应 29.0h， 生成 2,3-二氢-2-甲基-4(1h)-喹啉酮
  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

• Steroid receptor modulator compounds and methods
  申请人：Ligand Pharmaceuticals Incorporated

  公开号：US05688808A1

  公开（公告）日：1997-11-18

  Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

  披露了对类固醇受体具有高亲和力、高选择性调节剂的非类固醇化合物。还披露了包含这些化合物的药物组合物、使用所披露的化合物和组合物治疗需要类固醇受体激动剂或拮抗剂治疗的患者的方法，以及在制备这些化合物中有用的中间体和制备类固醇受体调节剂化合物的过程。
• Tricyclic steroid receptor modulator compounds and methods
  申请人：Ligand Pharmaceuticals Incorporated

  公开号：US05696130A1

  公开（公告）日：1997-12-09

  Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.

  披露了对类固醇受体具有高亲和力、高选择性调节剂的非类固醇化合物。还披露了包含这些化合物的药物组合物、使用所披露的化合物和组合物治疗需要类固醇受体激动剂或拮抗剂治疗的患者的方法，以及在制备这些化合物中有用的中间体和制备类固醇受体调节剂化合物的过程。
• Soluble beta amyloid precursor protein secretion promoters
  申请人：——

  公开号：US20030216398A1

  公开（公告）日：2003-11-20

  According to the present invention, there are provided compounds represented by formula (I): 1 [wherein R 1 and R 2 represent hydrogen atom, a lower alkyl group, etc.; ring A is an optionally substituted benzene ring, X is oxygen atom, etc.; and Y represents CH or N] or salts thereof, or prodrugs thereof, and use thereof as well as processes of manufacturing these compounds. The compounds of the present invention and the like possess a potent soluble beta amyloid precursor protein secretion promoting activity and suppress the functional disorders or apoptosis of cells, in particular neurons, mediated by the secreted soluble beta amyloid precursor proteins having a neurotrophic factor like property.

  根据本发明提供了以下公式（I）所代表的化合物：其中R1和R2代表氢原子、较低的烷基基团等；环A是一个可选择取代的苯环，X是氧原子等；Y代表CH或N；或其盐，或其前药，以及这些化合物的制造方法。本发明的化合物及类似化合物具有强大的可溶性β淀粉样前体蛋白分泌促进活性，并抑制细胞（特别是神经元）介导的具有类似神经营养因子特性的分泌可溶性β淀粉样前体蛋白引起的功能障碍或细胞凋亡。
• 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。
• Novel heterocyclic derivatives
  申请人：——

  公开号：US20040157850A1

  公开（公告）日：2004-08-12

  The object of the present invention is to provide soluble &bgr;-amyloid precursor protein secretory stimulators, which are effective in treating neurodegenerative diseases as well as cerebrovascular disorder-induced neuronopathy. More specifically, the present invention provides a novel compound of the following Formula (I) or a salt or prodrug thereof: 1 [wherein R 1 and R 2 each represent a hydrogen atom or a lower alkyl group, etc., Ar 1 and the ring B each represent an optionally substituted aromatic group, the ring A represents an optionally substituted benzene ring, the ring C represents an optionally substituted 4- to 8-membered ring which may further be condensed with an optionally substituted ring, X represents CH or N, and Y represents CH or N].

  本发明的目的是提供可溶性β-淀粉样前体蛋白分泌刺激剂，其对治疗神经退行性疾病以及脑血管疾病引起的神经病变具有有效性。更具体地说，本发明提供了以下式（I）的新化合物或其盐或前药：1 [其中，R1和R2分别代表氢原子或较低的烷基等，Ar1和环B分别代表可选取代的芳香族基团，环A代表可选取代的苯环，环C代表可选取代的4-至8-成员环，可以进一步与可选取代的环融合，X代表CH或N，Y代表CH或N]。