1-(4-hydroxy-2-methyl-1,1-dioxido-2H-1,2-benzothiazin-3-yl) phenyl methanone | 106345-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1-(4-hydroxy-2-methyl-1,1-dioxido-2H-1,2-benzothiazin-3-yl) phenyl methanone
• 英文别名: (4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazin-3-yl)-phenyl-methanone；3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide；3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide
• CAS: 106345-99-7
• 化学式: C₁₆H₁₃NO₄S
• 分子量: 315.35
• InChiKey: XAUOVEXCNXTYPT-UHFFFAOYSA-N

物化性质

• 沸点：
  493.4±55.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.68
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-2-methyl-1,1-dioxido-2H-1,2-benzothiazin-3-yl) phenyl methanone 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.36h， 生成 N'-(2,6-dichlorobenzylidene)-2-(4-methyl-5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-1(4H)-yl)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：

  saccharin sodium salt 在 sodium ethanolate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.58h， 生成 1-(4-hydroxy-2-methyl-1,1-dioxido-2H-1,2-benzothiazin-3-yl) phenyl methanone
  参考文献：
  名称：

  新型三唑标记吡唑融合萘5-噻嗪-5,5-二氧化物衍生物的合成，抑菌和抗氧化活性的研究

  摘要：

  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。

  DOI：

  10.1002/jhet.2013

文献信息

• 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。
• Discovery of cyclicsulfonamide derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitors
  作者：Se Hoan Kim、Ravirala Ramu、Sung Wook Kwon、Su-Hee Lee、Chi Hyun Kim、Seung Kyu Kang、Sang Dal Rhee、Myung Ae Bae、Sung Hoon Ahn、Duck Chan Ha、Hyae Gyeong Cheon、Ki Young Kim、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2009.12.035

  日期：2010.2

  A new series of cyclic sulfonamide derivatives was synthesized and evaluated for their ability to inhibit 11β-HSD1. Cyclic sulfonamides with phenylacetyl substituents at the 2-position showed nanomolar inhibitory activities. Among them, compound 4e exhibited a good in vitro inhibitory activity and selectivity toward human 11β-HSD2.

  合成了一系列新的环状磺酰胺衍生物，并评估了它们抑制11β-HSD1的能力。在2-位具有苯基乙酰基取代基的环状磺酰胺显示出纳摩尔抑制活性。其中，化合物4e对人11β-HSD2显示出良好的体外抑制活性和选择性。
• Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds
  作者：Kang Lei、Xue-Wen Hua、Yuan-Yuan Tao、Yang Liu、Na Liu、Yi Ma、Yong-Hong Li、Xiao-Hua Xu、Chui-Hua Kong

  DOI：10.1016/j.bmc.2015.11.032

  日期：2016.1

  A series of (2-benzoylethen-1-ol)-containing benzothiazine derivatives was synthesized, and their herbicidal activities were first evaluated. The bioassay results indicated that some of 3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide derivatives displayed good herbicidal activity in greenhouse testing, especially, compound 4w had good pre-emergent herbicidal activities against Brassica campestris, Amaranthus retroflexus and Echinochloa crusgalli even at a dosage of 187.5 g ha (1). More importantly, compound 4w displayed significant inhibitory activity against Arabidopsis thaliana HPPD and was identified as the most potent candidate with IC50 value of 0.48 mu M, which is better than the commercial herbicide sulctrione (IC50 = 0.53 mu M) and comparable with the commercial herbicide mesotrione (IC50 = 0.25 mu M). The structure-activity relationships was studied and provided some useful information for improving herbicidal activity. The present work indicated that (2-benzoylethen-1-ol)-containing 1,2-benzothiazine motif could be a potential lead structure for further development of novel HPPD inhibiting-based herbicides. (C) 2015 Elsevier Ltd. All rights reserved.
• ——
  作者：O. Yu. Korshunov

  DOI：10.1023/a:1026691311763

  日期：——
• 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：——