3-chloro-4-phenyl 4H-1,2,4-benzothiadiazine 1,1-dioxide | 107089-78-1

• 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-chloro-4-phenyl 4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 3-chloro-4-phenyl-4H-1,2,4-thiadiazine 1,1-dioxide；4H-1,2,4-Benzothiadiazine, 3-chloro-4-phenyl-, 1,1-dioxide；3-chloro-4-phenyl-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 107089-78-1
• 化学式: C₁₃H₉ClN₂O₂S
• 分子量: 292.746
• InChiKey: CBFVLMZNHRXBBF-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C(Solv: chloroform (67-66-3))
• 沸点：
  468.7±28.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-4-phenyl 4H-1,2,4-benzothiadiazine 1,1-dioxide 在 一水合肼 作用下， 以 氯仿 为溶剂， 生成 3-hydrazino-4-phenyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  某些新型10-取代的2-（4-哌啶基/苯基）-5,5-二氧杂[1,2,4]三唑[1,5-b] [1,2,4]的合成，结构分析和抗菌活性]苯并噻二嗪衍生物。

  摘要：

  新的10-取代的5,5-二氧-5,10-二氢[1,2,4]三唑[1,5-b]-[1,2,4]苯并噻二嗪芳基磺酰胺衍生物系列（10a-j和13a -f）被合成。这些化合物的结构在光谱数据，元素分析，X射线分析和量子化学计算的基础上得到确认。评价了这些化合物作为针对各种革兰氏阳性和革兰氏阴性细菌的抗菌剂的功效。在这些化合物10f和10i中，对大肠杆菌的活性最高，对大肠杆菌和枯草芽孢杆菌的活性最高的化合物13e。此外，与标准药物相比，其他化合物也显示出有效的抑制活性。

  DOI：

  10.1016/j.bmcl.2007.07.043
• 作为产物：
  描述：

  二苯胺 在 三氯化铝 、 五氯化磷 作用下， 以 硝基甲烷 为溶剂， 反应 1.5h， 生成 3-chloro-4-phenyl 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

• 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。
• A New, Facile Synthesis of 4-Alkyl- and Aryl-Substituted 3-Amino-4<i>H</i>-1,2,4-benzothiadiazine 1,1-Dioxides
  作者：A. V. Narender Reddy、Ahmed Kamal、P. B. Sattur

  DOI：10.1055/s-1986-31810

  日期：——

  A new efficient preparation of 4-alkyl- and aryl-substituted 3-amino- 4H-1,2,4-benzothiadiazine 1,1-dioxides (3) is described via the 3-chloro derivatives of 4-alkyl- and aryl substituted 3-oxo-2H-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxides, (1) on their treatment with aqueous ammonia solution.

  通过4-烷基和芳基取代的3-氧代-2H-3,4-二氢-1,2,4-苯并噻二嗪1,1-二氧化物（1）的3-氯衍生物与氨水溶液处理，描述了一种新的4-烷基和芳基取代的3-氨基-4H-1,2,4-苯并噻二嗪1,1-二氧化物（3）的高效制备方法。
• 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：——
• Anti-tubercular agents. Part 6: Synthesis and antimycobacterial activity of novel arylsulfonamido conjugated oxazolidinones
  作者：Ahmed Kamal、Rajesh V.C.R.N.C. Shetti、Shaik Azeeza、P. Swapna、M. Naseer A. Khan、Inshad Ali Khan、Sandeep Sharma、Sheikh Tasduq Abdullah

  DOI：10.1016/j.ejmech.2010.12.028

  日期：2011.3

  As a part of investigation of new anti-tubercular agents in this laboratory, herein we describe the synthesis of a new class of arylsulfonamido conjugated oxazolidinones. The in vitro activity of these conjugated (6a-f, 7a-d, 9a-c and 11a-c) molecules against Mycobacterium tuberculosis H(37)Rv by using rifampicin and linezolide as positive controls is discussed, compounds 7c and 9a-c are found to be the most active members in this series. Further, cytotoxicity of the potent conjugates of the series (7c, and 9a-c) was evaluated on human foreskin fibroblast (HFF) cells by using MTT assay. Finally, these studies suggest that compounds 7c and 9a may serve as promising lead scaffolds for further generation of new as anti-TB agents. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Anti-tubercular agents. Part 5: Synthesis and biological evaluation of benzothiadiazine 1,1-dioxide based congeners
  作者：Ahmed Kamal、Rajesh V.C.R.N.C. Shetti、Shaik Azeeza、S. Kaleem Ahmed、P. Swapna、A. Malla Reddy、Inshad Ali Khan、Sandeep Sharma、Sheikh Tasduq Abdullah

  DOI：10.1016/j.ejmech.2010.07.015

  日期：2010.10

  In an effort to discover new and effective chemotherapeutic agents from this laboratory for the treatment of tuberculosis, here in we describe the synthesis and biological evaluation of a series of novel benzo-thiadiazine 1,1-dioxide (BTD) based congeners by using rifampicin, streptomycin; ciprofloxacin and amphotericin as positive controls. Further, to understand structural requirements for exploring the structure activity relationship of BTDs, cytotoxicity and in vivo study of recently reported potent molecule 4 (MIC = 1 mu g/mL) is also discussed (C) 2010 Elsevier Masson SAS. All rights reserved.