3-hydrazino-4-ethyl-4H-1,2,4-benzothiadiazine 1,1-dioxide | 107089-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 3-hydrazino-4-ethyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 2H-1,2,4-Benzothiadiazin-3(4H)-one, 4-ethyl-, hydrazone, 1,1-dioxide；(4-ethyl-1,1-dioxo-1λ6,2,4-benzothiadiazin-3-yl)hydrazine
• CAS: 107089-80-5
• 化学式: C₉H₁₂N₄O₂S
• 分子量: 240.286
• InChiKey: DFOFKVOURVXSFW-UHFFFAOYSA-N

物化性质

• 熔点：
  296-298 °C(Solv: ethanol (64-17-5))
• 沸点：
  437.4±28.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-硝基噻吩-2-甲醛 、 3-hydrazino-4-ethyl-4H-1,2,4-benzothiadiazine 1,1-dioxide 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-ethyl-N-[(E)-(5-nitrothiophen-2-yl)methylideneamino]-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-amine
  参考文献：
  名称：

  抗结核药。第四部分：基于硝基杂环的1,2,4-苯并噻二嗪的合成及抗分枝杆菌的评估。

  摘要：

  在继续我们对苯并噻二嗪的早期研究工作的过程中，我们制备了一系列硝基呋喃，硝基噻吩和芳基呋喃偶联的苯并噻二嗪，并对它们的抗分枝杆菌和抗菌活性进行了评估。化合物2f之一显示出良好的体外抗分枝杆菌活性。所有合成的化合物均显示出中等至良好的抗菌活性。

  DOI：

  10.1016/j.bmcl.2007.07.027
• 作为产物：
  描述：

  4-乙基-2H-1,2,4-苯并噻二嗪-3(4H)-酮-1,1-二氧化物 在 五氯化磷 、 一水合肼 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 3-hydrazino-4-ethyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Anti-tubercular agents. Part 3. Benzothiadiazine as a novel scaffold for anti-Mycobacterium activity

  摘要：

  In an effort to develop new and more effective therapies to treat tuberculosis, a series of benzothiadiazine 1,1-dioxide derivatives were synthesized and their in vitro activity against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium intracellulare was evaluated. One of the compounds, 8c, exhibited potent anti-tubercular activity, particularly for the resistant strains and thus prompted us to investigate its in vivo profile. However, the in vivo testing in a mouse model of tuberculosis infection did not show significant anti-tubercular activity, probably because of its poor bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.063

文献信息

• Reddy, A. V. N.; Kamal, Ahmed; Sattur, P. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1295 - 1297
  作者：Reddy, A. V. N.、Kamal, Ahmed、Sattur, P. B.

  DOI：——

  日期：——
• REDDY A. V. N.; KAMAL AHMED; SATTUR P. B., INDIAN J. CHEM., 24,(1985) N 12, 1295-1297
  作者：REDDY A. V. N.、 KAMAL AHMED、 SATTUR P. B.

  DOI：——

  日期：——
• Anti-tubercular agents. Part 3. Benzothiadiazine as a novel scaffold for anti-Mycobacterium activity
  作者：Ahmed Kamal、K. Srinivasa Reddy、S. Kaleem Ahmed、M. Naseer A. Khan、Rakesh K. Sinha、J.S. Yadav、Sudershan K. Arora

  DOI：10.1016/j.bmc.2005.08.063

  日期：2006.2

  In an effort to develop new and more effective therapies to treat tuberculosis, a series of benzothiadiazine 1,1-dioxide derivatives were synthesized and their in vitro activity against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium intracellulare was evaluated. One of the compounds, 8c, exhibited potent anti-tubercular activity, particularly for the resistant strains and thus prompted us to investigate its in vivo profile. However, the in vivo testing in a mouse model of tuberculosis infection did not show significant anti-tubercular activity, probably because of its poor bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.
• Anti-tubercular agents. Part IV: Synthesis and antimycobacterial evaluation of nitroheterocyclic-based 1,2,4-benzothiadiazines
  作者：Ahmed Kamal、S. Kaleem Ahmed、K. Srinivasa Reddy、M. Naseer A. Khan、Rajesh V.C.R.N.C. Shetty、B. Siddhardha、U.S.N. Murthy、Inshad Ali Khan、Manoj Kumar、Sandeep Sharma、Anshu Beulah Ram

  DOI：10.1016/j.bmcl.2007.07.027

  日期：2007.10

  In continuation of our earlier work on benzothiadiazines, we have prepared a series of nitrofuran, nitrothiophene and arylfuran coupled benzothiadiazines and evaluated them for antimycobacterial and antibacterial activities. One of the compounds 2f has shown good in vitro antimycobacterial activity. All the synthesized compounds have shown moderate to good antibacterial activity.

  在继续我们对苯并噻二嗪的早期研究工作的过程中，我们制备了一系列硝基呋喃，硝基噻吩和芳基呋喃偶联的苯并噻二嗪，并对它们的抗分枝杆菌和抗菌活性进行了评估。化合物2f之一显示出良好的体外抗分枝杆菌活性。所有合成的化合物均显示出中等至良好的抗菌活性。