6-Brom-4,9-dihydropyrano<3,4-b>indol-1(3H)-on | 110977-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-Brom-4,9-dihydropyrano<3,4-b>indol-1(3H)-on
• 英文别名: 6-bromo-3,4-dihydropyrano[3,4-b]indol-1(9H)-one；6-bromo-4,9-dihydro-3H-pyrano[3,4-b]indol-1-one
• CAS: 110977-90-7
• 化学式: C₁₁H₈BrNO₂
• 分子量: 266.094
• InChiKey: CJJGAHPNAIBEDK-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(Solv: ethanol (64-17-5))
• 沸点：
  510.1±50.0 °C(Predicted)
• 密度：
  1.745±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Brom-4,9-dihydropyrano<3,4-b>indol-1(3H)-on 在 palladium on activated charcoal lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.25h， 生成 9H-吡啶[3,4-b]吲哚
  参考文献：
  名称：

  Indoles, 12. Mitt. Β-Carbolines from Lactones - 用于合成诺哈曼受体上的配体

  摘要：

  6-取代的 β-咔啉通过 5 个步骤从 α-乙二酰-δ-戊内酯 (1) 中制备，用于研究大鼠肝脏和猪脑中的诺哈曼结合位点。使用实施例 5a → 6a 优化了 Pd 催化的 N-苄基-四氢-β-咔啉与脱苄基的芳构化，然后转移到其他衍生物。在第 5 天，小时进行额外的氢解。通过溴化 1a 获得的 6d 提供了对放射性配体 3H-norharmane 的访问。

  DOI：

  10.1002/ardp.19943271107
• 作为产物：
  描述：

  3-(4-Bromphenylhydrazono)-5,6-dihydro-4H-pyran-2-on 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.08h， 以68%的产率得到6-Brom-4,9-dihydropyrano<3,4-b>indol-1(3H)-on
  参考文献：
  名称：

  Lactones, 11th edition. 4,9-dihydropyrano [3.4-b] indole-1 (3H) -ones from α-ethoxalyl-γ-lactones 的合成

  摘要：

  在 α-乙二酰基-γ-内酯 1a-d 开环和脱羧后，腙 4a-l 和 5 型吲哚内酯可以通过与苯肼反应制备。如果反应顺序转移到类似的 δ-内酯 6 和 10，吲哚合成成功，但内酯闭环不成功。

  DOI：

  10.1002/ardp.19873200105

文献信息

• Indoles, III Lactamisation of 4.9-Dihydropyrano [3.4-b]indol-1(3H)-ones. - A New Synthetic Route to the β-Carboline Ring System
  作者：Jochen Lehmann、Khadiga M. Ghoneim、Adel A. El-Gendy

  DOI：10.1002/ardp.19873200106

  日期：——

  Reaction of the pyrano[3.4‐b]indolones 1a‐d with aniline, benzylamine, phenylethylamine and propylamine at 200–210 °C yields the 2.3.4.9‐tetrahydro‐1H‐pyrido[3.4‐b]indol‐1‐ones 5a‐j, which can be converted to the 2.3.4.9‐tetrahydro‐1H‐pyrido[3.4‐b]indoles 6a‐j by reduction with LiAlH4. After treatment with methylamine and 2 only the amides 3 and 4 could be isolated. Unsubstituted tetrahydro‐β‐carboline

  吡喃并 [3.4-b] 吲哚酮 1a-d 与苯胺、苄胺、苯乙胺和丙胺在 200–210 °C 下反应生成 2.3.4.9-四氢-1H-吡啶并 [3.4-b] indole-1-ones 5a- j，可通过 LiAlH4 还原转化为 2.3.4.9-四氢-1H-吡啶并 [3.4-b] 吲哚 6a-j。用甲胺和 2 处理后，只能分离出酰胺 3 和 4。未取代的四氢 - β - 咔啉 7 可通过 6c 的区域选择性脱苄获得。
• Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
  作者：Daisuke Minehira、Daisuke Takeda、Hirokazu Urata、Atsushi Kato、Isao Adachi、Xu Wang、Yuji Matsuya、Kenji Sugimoto、Mayuko Takemura、Satoshi Endo、Toshiyuki Matsunaga、Akira Hara、Jun Koseki、Kayo Narukawa、Shuichi Hirono、Naoki Toyooka

  DOI：10.1016/j.bmc.2011.10.073

  日期：2012.1

  New substituted (1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 mu M) with clinically used epalrestat (IC50 = 0.1 mu M). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 mu M) and very high selectivity for AKR1B1 against AKR1A1 (311: 1) and AKR1B10 (253: 1) compared with epalrestat. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of New 9-glycosyl-4,9-dihydropyrano [3,4-<i>b</i>]indole-1(3<i>H</i>)-ones as Antibacterial Agents
  作者：Shaymaa E. Kassab、Gehan H. Hegazy、Nahed M. Eid、Kamelia M. Amin、Adel A. El-Gendy

  DOI：10.1080/15257770.2011.630334

  日期：2011.11

  A series of new 9-glycosyl-4,9-dihydropyrano[3,4-b]indole-1(3H)-ones 3 was synthesized in moderate to low yields. 4,9-Dihydropyrano[3,4-b]indole-1(3H)-ones (1) were coupled with different acetobromoglycopyranoses 2 in refluxing toluene in the presence of silver oxide to afford one coupling product of the respective N-glycosides. alpha-L-Arabinopyranosides 3j and 3m were the most active glycosides among the tested compounds against certain Gram positive and Gram negative bacterial strains.
• Synthesis and Evaluations of GLP-1 Secretion and Anti-Diabetic Effect in KKAy Mice of New Tricyclic Compounds
  作者：Naoki Toyooka、Isao Adachi、Daisuke Minehira、Daisuke Takeda、Shota Miyawaki、Atsushi Kato、Akira Miyazaki、Ryuta Miyatake、Masahito Umezaki、Kyoko Miura、Yoshiro Kitahara、Kenji Sugimoto、Yuji Matsuya

  DOI：10.3987/com-14-s(k)29

  日期：——

  Glucagon-like peptide-1 (GLP-1), which belongs to the family of incretins, plays important role for the regulation of plasma glucose. Accordingly, GLP-1-based therapies for type 2 diabetes have recognized as one of the most interesting target. In this study, we have found the new tricyclic compounds having strong GLP-1 secretion from human intestinal L cells, and anti-diabetic properties in spontaneously obese and diabetic KKAy mice. The most potent compound 5ka was obtained as the unexpected product, and we would like to report the details of the synthesis, structure elucidations, pharmacological activities on secretion of GLP-1, and anti-diabetic effects using diabetic KKAy mice.
• LEHMANN JOCHEN; GHONEIM KHADIGA M.; EL-GENDY ADEL A., ARCH. PHARM., 320,(1987) N 1, 30-36
  作者：LEHMANN JOCHEN、 GHONEIM KHADIGA M.、 EL-GENDY ADEL A.

  DOI：——

  日期：——