3-chloro-5,7-dinitro-1(2)H-indazole | 249627-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 3-chloro-5,7-dinitro-1(2)H-indazole
• 英文别名: 3-chloro-5,7-dinitroindazole；3-chloro-5,7-dinitro-1(2)H-indazole；3-Chlor-5,7-dinitro-1(2)H-indazol；3-chloro-5,7-dinitro-2H-indazole
• CAS: 249627-77-8
• 化学式: C₇H₃ClN₄O₄
• 分子量: 242.578
• InChiKey: LHRRFOWTHGCYCB-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C
• 沸点：
  483.7±40.0 °C(Predicted)
• 密度：
  1.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chloro-5,7-dinitro-1(2)H-indazole 在 ammonium sulfide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以86%的产率得到3-氯-5-硝基-2H-吲唑-7-胺
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Antimicrobial Activity of Indazole-Derived SAH/MTA Nucleosidase Inhibitors

  摘要：

  The structure-based design, synthesis, and biological activity of a novel indazole-containing inhibitor series for S-adenosyl homocysteine/methylthioadenosine (SAH/MTA) nucleosidase are described. Use of 5-aminoindazole as the core scaffold provided a structure-guided series of low nanomolar inhibitors with broad-spectrum antimicrobial activity. The implementation of structure-based methodologies provided a 6000-fold increase in potency over a short timeline (several months) and an economy of synthesized compounds.

  DOI：

  10.1021/jm0302039
• 作为产物：
  描述：

  3-氯-5-硝基-1H-吲唑 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以94%的产率得到3-chloro-5,7-dinitro-1(2)H-indazole
  参考文献：
  名称：

  宝石-二硝基杂环化合物的合成，开环反应以及向吲哚，吲唑和苯并恶嗪酮的转化

  摘要：

  报道了一些新颖的3,3,5,7-四硝基氧吲哚和4,4-二硝基吡唑-5-酮的合成及其对各种亲核试剂和亲电试剂的行为。与氢氧离子或仲胺的反应产生例如2-氨基-3，5-二硝基苯基二硝基甲烷的盐，其随后可以根据所使用的底物和条件进一步转化为吲唑，吲哚或苯并恶嗪酮。讨论了机制。

  DOI：

  10.1016/s0040-4020(99)00570-0

文献信息

• Syntheses of gem-dinitro heterocyclic compounds, their ring-opening reactions and transformations into indoles, indazoles and benzoxazinones
  作者：Jan Bergman、Solveig Bergman、Thomas Brimert

  DOI：10.1016/s0040-4020(99)00570-0

  日期：1999.8

  The synthesis of some novel 3,3,5,7-tetranitrooxindoles and 4,4-dinitropyrazol-5-ones and their behaviour towards various nucleophiles and electrophiles are reported. Reactions with hydroxide ions or secondary amines produced salts of e.g. 2-amino-3,5-dinitrophenyldinitromethane, which subsequently could be further transformed into indazoles, indoles or benzoxazinones depending upon substrate and conditions

  报道了一些新颖的3,3,5,7-四硝基氧吲哚和4,4-二硝基吡唑-5-酮的合成及其对各种亲核试剂和亲电试剂的行为。与氢氧离子或仲胺的反应产生例如2-氨基-3，5-二硝基苯基二硝基甲烷的盐，其随后可以根据所使用的底物和条件进一步转化为吲唑，吲哚或苯并恶嗪酮。讨论了机制。
• Kenner, Journal of the Chemical Society, 1914, vol. 105, p. 2736
  作者：Kenner

  DOI：——

  日期：——
• Structure-Based Design, Synthesis, and Antimicrobial Activity of Indazole-Derived SAH/MTA Nucleosidase Inhibitors
  作者：Xiaoming Li、Sam Chu、Victoria A. Feher、Mitra Khalili、Zhe Nie、Stephen Margosiak、Victor Nikulin、James Levin、Kelly G. Sprankle、Martina E. Tedder、Robert Almassy、Krzysztof Appelt、Kraig M. Yager

  DOI：10.1021/jm0302039

  日期：2003.12.1

  The structure-based design, synthesis, and biological activity of a novel indazole-containing inhibitor series for S-adenosyl homocysteine/methylthioadenosine (SAH/MTA) nucleosidase are described. Use of 5-aminoindazole as the core scaffold provided a structure-guided series of low nanomolar inhibitors with broad-spectrum antimicrobial activity. The implementation of structure-based methodologies provided a 6000-fold increase in potency over a short timeline (several months) and an economy of synthesized compounds.