6-(hydrazinocarbonylmethyl)-6H-indolo[2,3-b]quinoxaline | 116989-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-(hydrazinocarbonylmethyl)-6H-indolo[2,3-b]quinoxaline
• 英文别名: 2-(6H-2-6H-indolo[2,3-b]quinoxalin-6-yl)acetohydrazide；2-(6H-quinoxalino[2,3-b]indol-6-yl)acetohydrazide；2-(quinoxalino[2,3-b]indol-5-yl)acetohydrazine；indophenazine-6-acetic acid hydrazide；indophenazine-6-acetic acid hydrazine；2-Indolo[3,2-b]quinoxalin-6-ylacetohydrazide
• CAS: 116989-58-3
• 化学式: C₁₆H₁₃N₅O
• mdl: MFCD01415245
• 分子量: 291.312
• InChiKey: KPAMTPSYLLWTOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(hydrazinocarbonylmethyl)-6H-indolo[2,3-b]quinoxaline 、 L-阿拉伯糖 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 0.2h， 以93%的产率得到L-arabinose (6-indolo[2,3-b]quinoxalin-6-yl)acetylhydrazone
  参考文献：
  名称：

  El Ashry, El Sayed H.; Ramadan, El Sayed; Hamid, Hamida Abdel, Journal of Chemical Research, 2005, # 4, p. 229 - 232

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-(6H-indolo[2,3-b]quinoxalin-6-yl)acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 80.0 ℃ 、41.37 kPa 条件下， 反应 0.08h， 以95%的产率得到6-(hydrazinocarbonylmethyl)-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  微波辅助合成6-{（5-芳基-1,3,4-恶二唑-2-基）甲基} -6H-吲哚[2,3-b]喹喔啉

  摘要：

  从现成的1,2，{（6 H-吲哚[2,3 - b ]喹喔啉-6-基）甲基} -5-芳基-1,3,4-恶二唑中高效合成新的系列1，公开了在微波辐射条件下的2-二氨基苯和靛红。6-{（5-芳基-1,3,4-恶二唑-2-基）甲基} -6 H-吲哚并[2,3- b ]喹喔啉也可以通过2-（-在回流的POCl 3中将6 H-吲哚并[2,3 - b ]喹喔啉-6-基）乙酰肼与羧酸一起使用。与热反应方案相比，微波辅助合成快速，可在较低的操作温度下提高产品的收率，减少废物的产生。

  DOI：

  10.1002/jhet.2272

文献信息

• Microwave assisted synthesis of new indophenazine 1,3,5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1016/j.bmcl.2009.03.161

  日期：2009.5

  2-[1-(5,8-Dihydro quinoxalino[2,3-b]indoloacetyl)-3-(1-benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl] phenyl derivatives were synthesized from 2-(5,8-dihydro quinoxalino[2,3-b]indol-5-yl) acetohydrazide and (2E)-1-(1-benzofuran-2-yl)-4-phenylbut-2-en-1-ones derivatives using microwave-assisted route. The structures of all the compounds have been established on the basis of analytical and spectral data. Among the 14 compounds IPB-1, IPB-5, IPB-10, IPB-11 and IPB-12 were found good antibacterial activity and MICs were found bellow 10 mu g/mL against Escherichia coli, Pseudomonas aeruginosa and Streptococcus aureus, which can compared with sparfloxacin and norfloxacin. (C) 2009 Elsevier Ltd. All rights reserved.
• Potent in vitro and in vivo antitubercular activity of certain newly synthesized indophenazine 1,3,5-trisubstituted pyrazoline derivatives bearing benzofuran
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1007/s00044-010-9322-5

  日期：2011.4

  Fourteen newly synthesized derivatives of indophenazine 1,3,5-trisubstituted pyrazoline bearing benzofuran were prepared from benzofuran chalcones with indophenazine hydrazide through cycloaddition reaction. All the compounds were screened for their in vitro and in vivo antitubercular activity against drug resistant and multidrug-resistant Mycobacterium tuberculosis H37RV. The MIC50 and MIC90 were estimated and compared with rifampicin and gatifloxacin standard drugs. Nitro group containing at ortho 5j, meta 5e, furan ring containing 5m and ortho 5i, para 5h chloro containing compounds were exhibited significant in vitro, in vivo antitubercular activity against standard drugs.