1-chloro-5-hydrazino-9,10-anthracenedione | 261962-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-chloro-5-hydrazino-9,10-anthracenedione
• 英文别名: 5-chloro-1-anthraquinonylhydrazine；1-chloro-5-hydrazino-anthraquinone；5-Chlor-anthrachinonyl-(1)-hydrazin；1-Chlor-5-hydrazino-anthrachinon；1-chloro-5-hydrazinylanthracene-9,10-dione
• CAS: 261962-07-6
• 化学式: C₁₄H₉ClN₂O₂
• 分子量: 272.691
• InChiKey: FQDOIAUIGLIYTG-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C
• 沸点：
  528.7±50.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.19
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-chloro-5-hydrazino-9,10-anthracenedione 在 吡啶 、 一水合肼 作用下， 生成 1,5-dihydrazino-anthraquinone
  参考文献：
  名称：

  Moehlau, Chemische Berichte, 1912, vol. 45, p. 2247

  摘要：

  DOI：
• 作为产物：
  描述：

  1,5-二氯蒽醌 在 一水合肼 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以69%的产率得到1-chloro-5-hydrazino-9,10-anthracenedione
  参考文献：
  名称：

  EDC-mediated condensations of 1-chloro-5-hydrazino-9,10-anthracenedione, 1-hydrazino-9,10-anthracenedione, and the corresponding anthrapyrazoles

  摘要：

  The EDC-mediated condensation of 1-chloro-5-hydrazino-9,10-anthracenedione afforded an N-1 acyl anthrapyrazole instead of the expected hydrazide. The regiochemistry of the N-acyl substituent was assigned on the basis of an extensive set of NMR experiments, and identification of this isomer Suggests a reaction sequence based on initial acylation and Subsequent cyclization. In contrast, the parallel reaction of 1-hydrazino-9,10-anthracenedione proceeded to afford the expected hydrazide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.041

文献信息

• Compounds and methods for detecting tripeptidyl protease I
  申请人：——

  公开号：US20040185520A1

  公开（公告）日：2004-09-23

  The present invention provides compounds useful for the detection of the enzyme tripeptidyl protease I (TPP-1). The invention also provides methods of making such compounds, methods of using such compounds, and kits and compositions containing such compounds. In one embodiment, Gly-L-Pro-L-Ser-1-anthraquinonylhydrazide, in combination with p-anisaldehyde, is used to detect TPP-1.

  本发明提供了用于检测三肽蛋白酶I（TPP-1）的化合物。该发明还提供了制备这种化合物的方法，使用这种化合物的方法，以及包含这种化合物的试剂盒和组合物。在一个实施例中，Gly-L-Pro-L-Ser-1-anthraquinonylhydrazide与对甲氧基苯甲醛结合使用以检测TPP-1。
• Tripeptide Probes for Tripeptidyl Protease I Production via Gene Transfer
  作者：MeeKyoung Kim、Qinwen Mao、Beverly L. Davidson、David F. Wiemer

  DOI：10.1021/jm020525x

  日期：2003.4.1

  Tripeptides derived from 5-chloroanthraquinone hydrazide and anthraquinone hydrazide have been prepared as potential reagents to probe cellular expression of tripeptidyl protease I (TPP-I). Attempted chemical synthesis of Gly-L-Pro-L-Ala-chloroanthraquinone hydrazide, a compound that had been reported to serve as a substrate for this enzyme, was complicated by formation of a pyrazoloquinone. In contrast, formation of pyrazoloquinones was not observed during coupling reactions with anthraquinone hydrazide, and several tripeptide derivatives of this compound were prepared. The most attractive probe for TPP-I activity in tests with mouse kidney tissue sections proved to be Gly-L-Pro-L-Ser anthraquinone hydrazide.
• US6824998B2
  申请人：——

  公开号：US6824998B2

  公开（公告）日：2004-11-30
• Moehlau, Chemische Berichte, 1912, vol. 45, p. 2247
  作者：Moehlau

  DOI：——

  日期：——
• EDC-mediated condensations of 1-chloro-5-hydrazino-9,10-anthracenedione, 1-hydrazino-9,10-anthracenedione, and the corresponding anthrapyrazoles
  作者：MeeKyoung Kim、David F Wiemer

  DOI：10.1016/j.tetlet.2004.04.041

  日期：2004.6

  The EDC-mediated condensation of 1-chloro-5-hydrazino-9,10-anthracenedione afforded an N-1 acyl anthrapyrazole instead of the expected hydrazide. The regiochemistry of the N-acyl substituent was assigned on the basis of an extensive set of NMR experiments, and identification of this isomer Suggests a reaction sequence based on initial acylation and Subsequent cyclization. In contrast, the parallel reaction of 1-hydrazino-9,10-anthracenedione proceeded to afford the expected hydrazide. (C) 2004 Elsevier Ltd. All rights reserved.