4-methyl-3-phenyl-2,4-dihydrobenzo[e]pyrazolo[4,3-c][1,2]thiazine 5,5-dioxide | 1421740-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-3-phenyl-2,4-dihydrobenzo[e]pyrazolo[4,3-c][1,2]thiazine 5,5-dioxide
• 英文别名: 4-methyl-3-phenyl-2,4-dihydropyrazolo[4,3-c][1,2]benzothiazine-5,5-dioxide；4-Methyl-3-phenyl-2,4-dihydropyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide；4-methyl-3-phenyl-1H-pyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide
• CAS: 1421740-44-4；17833-87-3
• 化学式: C₁₆H₁₃N₃O₂S
• 分子量: 311.364
• InChiKey: HPFBBGGQEWQWLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-3-phenyl-2,4-dihydrobenzo[e]pyrazolo[4,3-c][1,2]thiazine 5,5-dioxide 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.04h， 生成 2-(4-methyl-5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-1(4H)-yl)-N'-(2-nitrobenzylidene)acetohydrazide
  参考文献：
  名称：

  Synthesis, molecular docking and antiviral screening of novel N′-substitutedbenzylidene-2-(4-methyl-5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-1(4H)-yl)acetohydrazides

  摘要：

  N'-Substitutedbenzylidene-2-(4-methyl-5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-1(4H)-yl)acetohydrazides (7a-u) were synthesized through a multistep reaction. The final compounds were screened for anti-HIV-1 and cytotoxic activities. Among these compounds, 7l and 7m exhibited the most significant anti-HIV-1 activity with EC50 values of 5.4 and 3.3 mu M, respectively, while 7j showed moderate anti-HIV activity with an EC50 value 17.1 mu M. Molecular docking into HIV-1 Reverse Transcriptase also showed the best fit for 7l and 7m followed by 7j. In addition, compounds 7b, 7f, 7h, 7k, 7o, and 7s exhibited no toxicity in all the three cell lines used i.e., primary human PBM, CEM, and Vero cells, while 7e, 7g, 7i, 7n, 7p, 7q, and 7t exhibited no cytotoxic activity in primary human PBM cells. Moreover, it was found through molecular docking that compounds 7l, 7m, and 7j bound efficiently in the NTP-binding pocket of HIV-1 Reverse Transcriptase. The structure-activity relationship established on these results would facilitate the further development of new HIV inhibitors based on this skeleton.

  DOI：

  10.1007/s00044-013-0879-7
• 作为产物：
  描述：

  (Z)-3-benzylidene-2,3-dihydro-2-methyl-1,2-benzothiazin-4-one 1,1-dioxide 在 sodium hydroxide 、 一水合肼 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 18.0h， 生成 4-methyl-3-phenyl-2,4-dihydrobenzo[e]pyrazolo[4,3-c][1,2]thiazine 5,5-dioxide
  参考文献：
  名称：

  Dalla Croce, Piero; Del Monaco, Demetrio; La Rosa, Concetta, Journal of the Chemical Society. Perkin transactions I, 1986, p. 299 - 302

  摘要：

  DOI：

文献信息

• Studies on Synthesis of Novel Triazole Tagged Pyrazole Fused Naphthalene 5-Thiazine-5,5-dioxide Derivatives, Their Antimicrobial, and Antioxidant Activity
  作者：G. Malla Reddy、P. Nagender、R. Naresh Kumar、J. H. Ahn、K. Pranay Kumar、A. K. R. Kanugula、K. V. S. Rama Krishna、S. Kotamraju、B. Narsaiah

  DOI：10.1002/jhet.2013

  日期：2014.8

  A series of novel triazole tagged pyrazole fused naphthalene-5-thiazine-5,5-dioxide derivatives and were synthesized starting from sodium salt of saccharin . The structure of each intermediate and products was established on the basis of spectroscopy data. All the synthesized compounds and were screened against various bacterial and fungal strains but found to show no activity up to 150-µg/mL concentration

  一系列新型的三唑标记的吡唑稠合萘-5-噻嗪-5,5-二氧化物衍生物 和 从糖精钠盐开始合成 。根据光谱数据确定每种中间体和产物的结构。所有合成的化合物 和 对各种细菌和真菌菌株进行了筛选，但发现在浓度高达150 µg / mL时无活性。进一步筛选抗氧化剂性能得到了有希望的化合物。
• Novel structural hybrids of pyrazolobenzothiazines with benzimidazoles as cholinesterase inhibitors
  作者：Sana Aslam、Sumera Zaib、Matloob Ahmad、John M. Gardiner、Aqeel Ahmad、Abdul Hameed、Norbert Furtmann、Michael Gütschow、Jürgen Bajorath、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2014.03.035

  日期：2014.5

  efficiently synthesized starting from saccharin sodium salt. Pyrazolo[4,3-c][1,2]benzothiazine scaffolds were N-arylated by using p-fluorobenzaldehyde, followed by the incorporation of a benzimidazole or similar ring systems by treatment with arylenediamines. These phenylene-connected hybrid compounds were investigated as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE)

  从糖精钠盐开始有效地合成了两个系列的新型基于吡唑并苯并噻嗪的杂化化合物。通过使用对氟苯甲醛对吡唑并[4,3- c ] [1,2]苯并噻嗪支架进行N-芳基化，然后通过亚芳基二胺处理引入苯并咪唑或类似的环系统。研究了这些与亚苯基连接的杂化化合物作为乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的潜在抑制剂。化合物12d和12k是最有效的AChE抑制剂，IC 50值分别为11和13 nM，而6j（IC 50 = 17 nM）被证明是最有效的BuChE抑制剂，对BuChE的选择性比AChE高。还对人的AChE和BuChE进行了分子对接研究，以表明可能的结合方式，其中抑制剂的延伸结构沿两种酶的活性位点排列。
• Pyrazolobenzothiazine-based carbothioamides as new structural leads for the inhibition of monoamine oxidases: design, synthesis, in vitro bioevaluation and molecular docking studies
  作者：Syed Mobasher Ali Abid、Sana Aslam、Sumera Zaib、Syeda Mahwish Bakht、Matloob Ahmad、Muhammad Makshoof Athar、John M. Gardiner、Jamshed Iqbal

  DOI：10.1039/c6md00570e

  日期：——

  their ability to inhibit monoamine oxidases (MAO). Compound 3b was found to be a very potent MAO-A inhibitor with an IC50 value of 0.003 ± 0.0007 μM, while compound 4d was the most effective inhibitor of MAO-B having an IC50 value of 0.02 ± 0.001 μM. Molecular docking studies were performed to identify the probable binding modes in the active site of the monoamine oxidase enzymes. The synthetic and

  以糖精为原料合成了两个新系列的吡唑并苯并噻嗪基硫代碳酰胺（3a-o和4a-o ）。研究了合成的衍生物抑制单胺氧化酶 (MAO) 的能力。化合物3b被发现是一种非常有效的 MAO-A 抑制剂，IC 50值为 0.003 ± 0.0007 μM，而化合物4d是最有效的 MAO-B 抑制剂，IC 50值为 0.02 ± 0.001 μM。进行分子对接研究以确定单胺氧化酶活性位点中可能的结合模式。目前工作中的合成和计算研究表明，这些新发现的抑制剂可以作为探索和优化针对帕金森病的潜在治疗药物的有力起点。
• CROCE, P. D.;MONACO, D. D.;ROSA, C. LA, J. CHEM. SOC. PERKIN TRANS., 1986, N 2, 299-302
  作者：CROCE, P. D.、MONACO, D. D.、ROSA, C. LA

  DOI：——

  日期：——