2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-9-carbaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-9-carbaldehyde
• 英文别名: 10-oxo-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracene-8-carbaldehyde；4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraene-6-carbaldehyde
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: GGRHSDPGZVBUCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-9-carbaldehyde 在 劳森试剂 、 咪唑 、 三乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 2-(9-{1-[(tert-butyldimethylsilyl)oxy]but-3-yn-1-yl}-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11- ylidene)malononitrile
  参考文献：
  名称：

  扩展绿色香豆素 Photocages 的调色板——寡核苷酸片段化和高级 5'-Caps

  摘要：

  在本文中，对吸收绿光的 DCCM 光笼进行了修改，不仅允许寡核苷酸释放（OFF→ON），还允许寡核苷酸片段化，从而提供额外的调节途径（ON→OFF），从而在基因调控中提供更多自由。此外，通过硬化香豆素核心提高了 DCCM 的解笼效率，导致额外的 20 nm 红移。

  DOI：

  10.1002/chem.202300390
• 作为产物：
  描述：

  8-(1,2-dihydroxy-ethyl)-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以74%的产率得到2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-9-carbaldehyde
  参考文献：
  名称：

  [EN] LIGANDS FOR ALDOKETOREDUCTASES
  [FR] LIGANDS POUR ALDOCETOREDUCTASES

  摘要：

  公开号：

  WO2006023821A3

文献信息

• Ligands for Aldoketoreductases
  申请人：Yee Dominic J.

  公开号：US20100048604A1

  公开（公告）日：2010-02-25

  The present invention relates to compounds useful for detecting the activity of human aldoketoreductase 1Cs, compounds useful for competitively inhibiting human aldoketoreductase 1Cs and compounds useful for treating human aldoketoreductase 1C-related cancers, as well as pharmaceutical compositions and methods of manufacture thereof.

  本发明涉及用于检测人类醛基酮还原酶1Cs活性的化合物，用于竞争性抑制人类醛基酮还原酶1Cs的化合物以及用于治疗人类醛基酮还原酶1C相关癌症的化合物，以及其制药组合物和制造方法。
• Bidirectional Neuronal Actuation by Uncaging with Violet and Green Light
  作者：Lorenzo Sansalone、Jun Zhao、Linh T. B. Nguyen、Swati Gupta、Deanna L. Benson、Manabu Abe、Graham C. R. Ellis‐Davies

  DOI：10.1002/anie.202315726

  日期：2024.3.22

  We have developed a photochemical protecting group that enables wavelength selective uncaging using green versus violet light. Change of the exocyclic oxygen of the laser dye coumarin‐102 to sulfur, gave thio‐coumarin‐102, a new chromophore with an absorption ratio at 503/402 nm of 37. Photolysis of thio‐coumarin‐102 caged γ‐aminobutyric acid was found to be highly wavelength selective on neurons, with normalized electrical responses >100‐fold higher in the green versus violet channel. When partnered with coumarin‐102 caged glutamate, we could use whole cell violet and green irradiation to fire and block neuronal action potentials with complete orthogonality. Localized irradiation of different dendritic segments, each connected to a neuronal cell body, in concert with 3‐dimenional Ca²⁺ imaging, revealed that such inputs could function independently. Chemical signaling in living cells always involves a complex balance of multiple pathways, use of (thio)‐coumarin‐102 caged compounds will enable arbitrarily timed flashes of green and violet light to interrogate two independent pathways simultaneously.
• [EN] LIGANDS FOR ALDOKETOREDUCTASES<br/>[FR] LIGANDS POUR ALDOCETOREDUCTASES
  申请人：UNIV COLUMBIA

  公开号：WO2006023821A3

  公开（公告）日：2009-04-02
• Extending the Palette of Green Coumarin Photocages – Oligonucleotide Fragmentation and Superior 5’‐Caps
  作者：Janik Kaufmann、Jonas Wolf、Alexander Heckel

  DOI：10.1002/chem.202300390

  日期：——

  In this article, the green-light-absorbing DCCM photocage was modified to not just allow oligonucleotide release (OFF→ON) but also oligonucleotide fragmentation and thereby serve an additional regulation pathway (ON→OFF) that gives more freedom in gene regulation. Furthermore, the uncaging efficiency of DCCM by rigidification of the coumarin core was improved, resulting in an additional 20 nm red-shift

  在本文中，对吸收绿光的 DCCM 光笼进行了修改，不仅允许寡核苷酸释放（OFF→ON），还允许寡核苷酸片段化，从而提供额外的调节途径（ON→OFF），从而在基因调控中提供更多自由。此外，通过硬化香豆素核心提高了 DCCM 的解笼效率，导致额外的 20 nm 红移。