2-(2-(3-methoxyphenyl)-2-oxoethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide | 184773-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-(3-methoxyphenyl)-2-oxoethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide
• 英文别名: 2-[2-(3-methoxyphenyl)-2-oxoethyl]-1,2-benzothiazol-3(2H)-one 1,1-dioxide；2-(2-hydroxy-2-(3-methoxyphenyl)ethyl)benzo[d]isothiazol-3(2H)-one；2-[2-(3-Methoxyphenyl)-2-oxoethyl]-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione；2-[2-(3-methoxyphenyl)-2-oxoethyl]-1,1-dioxo-1,2-benzothiazol-3-one
• CAS: 184773-44-2
• 化学式: C₁₆H₁₃NO₅S
• 分子量: 331.349
• InChiKey: MOSTYHKYQCUWGB-UHFFFAOYSA-N

物化性质

• 沸点：
  548.4±56.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-(3-methoxyphenyl)-2-oxoethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.11.032
• 作为产物：
  描述：

  糖精 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-(3-methoxyphenyl)-2-oxoethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide
  参考文献：
  名称：

  开放的基于糖精的仲磺酰胺可作为与癌症相关的碳酸酐酶IX和XII亚型的有效和选择性抑制剂。

  摘要：

  合成了大量基于开放糖精支架的新型仲磺酰胺，并将其评估为人类碳酸酐酶的四种不同同工型的选择性抑制剂（hCA I，II，IX和XII，EC 4.2.1.1）。它们是通过新合成的N-烷基化糖精衍生物的还原性开环获得的，并且显示出对两种胞质脱靶hCA I和II（Kis> 10 µM）无活性。有趣的是，这些化合物在低纳摩尔范围内抑制hCA IX，Kis在20至298 nM之间，并且是hCA XII同工酶的极强抑制剂（Kis在4.3至432 nM之间）。由于hCA IX和XII是最近被证实可作为药物靶标的与癌症相关的亚型，因此这些结果代表了开发新的抗癌候选药物的重要目标。最后，

  DOI：

  10.1080/14756366.2016.1235040

文献信息

• nBu4NI-Catalyzed oxidative imidation of ketones with imides: synthesis of α-amino ketones
  作者：Yunhe Lv、Yan Li、Tao Xiong、Yu Lu、Qun Liu、Qian Zhang

  DOI：10.1039/c3cc48887j

  日期：——

  nBu4NI-Catalyzed oxidative imidation of ketones and imides for the synthesis of alpha-amino ketones were realized for the first time. The methodology is characterized by its wide substrate scope even for acetone with readily available phthalimide, saccharin and succinimide, which opens a new pathway for direct imidation of ketones.

  首次实现了nBu4NI-催化的酮类和酰亚胺的氧化酰亚胺化和酰亚胺化。该方法的特点是，即使对于丙酮和易得的邻苯二甲酰亚胺，糖精和琥珀酰亚胺，其底物范围也很广，这为直接酰亚胺化酮打开了一条新途径。
• A novel library of saccharin and acesulfame derivatives as potent and selective inhibitors of carbonic anhydrase IX and XII isoforms
  作者：Simone Carradori、Daniela Secci、Celeste De Monte、Adriano Mollica、Mariangela Ceruso、Atilla Akdemir、Anatoly P. Sobolev、Rossella Codispoti、Federica De Cosmi、Paolo Guglielmi、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2016.01.038

  日期：2016.3

  Small libraries of N-substituted saccharin and N-/O-substituted acesulfame derivatives were synthesized and tested as atypical and selective inhibitors of four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). Most of them inhibited hCA XII in the low nanomolar range, hCA IX with KIs ranging between 19 and 2482 nM, whereas they were poorly active against hCA II (KIs

  合成了小的N-取代的糖精和N- / O-取代的乙酰磺胺衍生物文库，并作为人类碳酸酐酶的四种不同同工型（hCA I，II，IX和XII，EC 4.2.1.1）的非典型和选择性抑制剂进行了测试。他们中的大多数在低纳摩尔范围内抑制hCA XII，hCA IX的K I在19和2482 nM之间，而对hCA II（K I s> 10μM）和hCA I（K I范围介于318 nM和50μM之间。由于hCA I和II是普遍存在的脱靶同工型，而癌症相关的同工型hCA IX和XII最近已被验证为药物靶标，因此这些结果在开发新的抗癌候选药物中取得了令人鼓舞的成就。此外，这些抑制剂的结构中缺乏经典的锌结合基团为不同的抑制机制开启了创新的，尚未探索的场景，这可能解释了高抑制选择性。已经进行了一种计算方法以进一步合理化生物学数据并表征这些抑制剂中某些抑制剂的结合模式。
• Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling
  作者：Furqan Ahmad Saddique、Matloob Ahmad、Usman Ali Ashfaq、Muhammad Muddassar、Sadia Sultan、Magdi E. A. Zaki

  DOI：10.3390/ph15010106

  日期：——

  inhibitory potential against α-glucosidase and α-amylase enzymes. The compounds with chloro, bromo and methyl substituents demonstrated good inhibition of α-glucosidase enzymes having IC50 values in the range of 25.88–46.25 μM, which are less than the standard drug, acarbose (IC50 = 58.8 μM). Similarly, some derivatives having chloro, bromo and nitro substituents were observed potent inhibitors of α-amylase

  糖尿病（DM）是一种复杂的代谢性疾病，是由于胰岛素功能不敏感或胰岛素分泌减少而导致餐后高血糖。 α-葡萄糖苷酶抑制剂（AGI）和α-淀粉酶抑制剂（AAI）阻断消化酶的功能，从而延迟碳水化合物的水解过程，最终有助于控制餐后高血糖。合成了多样化的2-(3-(3-甲氧基苯甲酰基)-4-羟基-1,1-二氧化-2H-苯并[e][1,2]噻嗪-2-基)-N-芳基乙酰胺并评价了其性能对 α-葡萄糖苷酶和 α-淀粉酶的体外抑制潜力。具有氯、溴和甲基取代基的化合物对α-葡萄糖苷酶具有良好的抑制作用，IC50值在25.88-46.25 μM范围内，低于标准药物阿卡波糖（IC50 = 58.8 μM）。类似地，一些具有氯、溴和硝基取代基的衍生物被观察到是α-淀粉酶的有效抑制剂，其IC50值为7.52至15.06 μM，低于阿卡波糖（IC50 = 17.0 μM）。此外，最有效的化合物，N-(4-溴苯基)-2-(
• 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.
• Open saccharin-based secondary sulfonamides as potent and selective inhibitors of cancer-related carbonic anhydrase IX and XII isoforms
  作者：Melissa D’Ascenzio、Paolo Guglielmi、Simone Carradori、Daniela Secci、Rosalba Florio、Adriano Mollica、Mariangela Ceruso、Atilla Akdemir、Anatoly P. Sobolev、Claudiu T. Supuran

  DOI：10.1080/14756366.2016.1235040

  日期：2017.1.1

  A large number of novel secondary sulfonamides based on the open saccharin scaffold were synthesized and evaluated as selective inhibitors of four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). They were obtained by reductive ring opening of the newly synthesized N-alkylated saccharin derivatives and were shown to be inactive against the two cytosolic off-target

  合成了大量基于开放糖精支架的新型仲磺酰胺，并将其评估为人类碳酸酐酶的四种不同同工型的选择性抑制剂（hCA I，II，IX和XII，EC 4.2.1.1）。它们是通过新合成的N-烷基化糖精衍生物的还原性开环获得的，并且显示出对两种胞质脱靶hCA I和II（Kis> 10 µM）无活性。有趣的是，这些化合物在低纳摩尔范围内抑制hCA IX，Kis在20至298 nM之间，并且是hCA XII同工酶的极强抑制剂（Kis在4.3至432 nM之间）。由于hCA IX和XII是最近被证实可作为药物靶标的与癌症相关的亚型，因此这些结果代表了开发新的抗癌候选药物的重要目标。最后，