[1,3]dioxolo[4,5-i]phenanthridine | 209672-82-2

• 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
• 英文名称: [1,3]dioxolo[4,5-i]phenanthridine
• 英文别名: 12,14-Dioxa-8-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),3,5,8,11(15),16-heptaene
• CAS: 209672-82-2
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: BDHOVBWCQYUPEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1,3]dioxolo[4,5-i]phenanthridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 [1,3]dioxolo[4,5-i]phenanthridine-5-oxide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

  摘要：

  Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-X-L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X-L. and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC50 values.

  DOI：

  10.1021/jm8005433
• 作为产物：
  描述：

  5-chloro-1,3-benzodioxole-4-carboxaldehyde 、 2-氨基苯硼酸频哪醇酯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以86%的产率得到[1,3]dioxolo[4,5-i]phenanthridine
  参考文献：
  名称：

  级联 CC 和 CN 键的形成：菲啶和稠合喹啉的直接合成

  摘要：

  已经开发了一种 Pd 催化的级联工艺，用于分别从各种 β-氯 α,β-不饱和醛和 2-氯芳基醛合成喹啉和菲啶衍生物，收率良好。该反应通过 Pd 催化的级联碳 - 碳和碳 - 氮键在单个反应容器中形成。必需的β-氯α,β-不饱和醛是由相应的羰基化合物有效合成的。配体 Sphos 与 Pd(OAc)2 的使用对于本级联工艺的成功实施至关重要。该合成方案也适用于三球定生物碱的克级合成。

  DOI：

  10.1002/ejoc.201600220

文献信息

• METHODS OF SCREENING USING AMPHIBIANS
  申请人：Brändli André W.

  公开号：US20120010103A1

  公开（公告）日：2012-01-12

  High-throughput methods of screening agents for activities affecting renal, cardiac, blood or lymphatic vascular development and functions in amphibians in multiwell plates are provided. Also provided are novel compounds that modulate blood and lymphatic vascular development.
• Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinol­ines
  作者：Ashwini Borah、Pranjal Gogoi

  DOI：10.1002/ejoc.201600220

  日期：2016.4

  Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro α,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon–carbon and carbon–nitrogen bond formation in a single reaction vessel. The requisite β-chloro α,β-unsaturated aldehydes were efficiently

  已经开发了一种 Pd 催化的级联工艺，用于分别从各种 β-氯 α,β-不饱和醛和 2-氯芳基醛合成喹啉和菲啶衍生物，收率良好。该反应通过 Pd 催化的级联碳 - 碳和碳 - 氮键在单个反应容器中形成。必需的β-氯α,β-不饱和醛是由相应的羰基化合物有效合成的。配体 Sphos 与 Pd(OAc)2 的使用对于本级联工艺的成功实施至关重要。该合成方案也适用于三球定生物碱的克级合成。
• Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors
  作者：Paul H. Bernardo、Kah-Fei Wan、Thirunavukkarasu Sivaraman、Jin Xu、Felicity K. Moore、Alvin W. Hung、Henry Y. K. Mok、Victor C. Yu、Christina L. L. Chai

  DOI：10.1021/jm8005433

  日期：2008.11.13

  Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-X-L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X-L. and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC50 values.