2-(4-(tert-butyl)phenyl)benzo[d]isothiazol-3(2H)-one | 1186645-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(4-(tert-butyl)phenyl)benzo[d]isothiazol-3(2H)-one
• 英文别名: 2-(4-tert-butylphenyl)-2-hydrobenzo[d]isothiazol-3-one；2-(4-Tert-butylphenyl)-1,2-benzothiazol-3-one
• CAS: 1186645-37-3
• 化学式: C₁₇H₁₇NOS
• 分子量: 283.394
• InChiKey: LSWCOOVGYNLMFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-tert-butylphenyl)-2-iodobenzamide 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 4-二甲氨基吡啶 、 nickel(II) ferrite 作用下， 以 二甲基亚砜 为溶剂， 以85 %的产率得到2-(4-(tert-butyl)phenyl)benzo[d]isothiazol-3(2H)-one
  参考文献：
  名称：

  通过 NiFe2O4 催化 2-卤代苯甲酰苯胺与硫属元素的伴随环化及其后期转化，无配体获得苯并异噻唑酮和苯并异硒唑酮

  摘要：

  本工作展示了一种有效的无配体合成多种苯并异噻唑酮和苯并异硒唑酮的方法，该方法利用 X-N（X = S，Se）交叉偶联中的磁性可回收纳米镍铁氧体催化剂与 2-碘苯苯胺和元素硫或硒的同时环化. 该协议的特点是使用可回收的纳米镍铁氧体催化剂、底物多样性、廉价的硫和硒粉作为硫属化物试剂、较低的反应温度和合成分子的有用应用。NiFe 2 O 4的罕见化学X-N 交叉偶联反应很好地补充了合成 S-N 或 Se-N 杂环的常规方法。采用简单的水热法制备了镍铁氧体纳米粒子，并通过XRD、SEM、TEM、HRTEM、SAED、能量色散X射线光谱、XPS、ICP-AES和FT-IR分析对其进行了表征。催化剂易于回收和产品转化率高，使该协议具有实际经济性。使用 TBN 和氧气作为正确的氧化剂组合，苯并异噻唑酮中易氧化的硫转化为各种糖精基序。此外，含 S-N 和 Se-N 的杂环都被放大并进一步转化为新的 C-H

  DOI：

  10.1039/d2nj04326b

文献信息

• Potent, Selective, and Orally Available Benzoisothiazolone Phosphomannose Isomerase Inhibitors as Probes for Congenital Disorder of Glycosylation Ia
  作者：Russell Dahl、Yalda Bravo、Vandana Sharma、Mie Ichikawa、Raveendra-Panickar Dhanya、Michael Hedrick、Brock Brown、Justin Rascon、Michael Vicchiarelli、Arianna Mangravita-Novo、Li Yang、Derek Stonich、Ying Su、Layton H. Smith、Eduard Sergienko、Hudson H. Freeze、Nicholas D. P. Cosford

  DOI：10.1021/jm101401a

  日期：2011.5.26

  We report the discovery and validation of a series of benzoisothiazolones as potent inhibitors of phosphomannose isomerase (PM), an enzyme that converts mannose-6-phosphate (Man-6-P) into fructose-6-phosphate (Fru-6-P) and, more importantly, competes with phosphomannomutase 2 (PMM2) for Man-6-P, diverting this substrate from critical protein glycosylation events. In congenital disorder of glycosylation type Ia, PMM2 activity is compromised.; thus, PMI inhibition is a potential strategy for the development of therapeutics. High-throughput screening (HTS) and subsequent chemical optimization led to the identification of a novel class of benzoisothiazolones as potent PMI inhibitors having little or no PMM2 inhibition. Two complementary synthetic routes were developed, enabling the critical structural requirements for activity to be determined, and the compounds were subsequently profiled in biochemical and cellular assays to assess efficacy. The most promising compounds were also profiled for bioavailability parameters, including metabolic stability, plasma stability, and permeability. The pharmacokinetic profile of a representative of this series (compound 19; ML089) was also assessed, demonstrating the potential of this series for in vivo efficacy when dosed orally in disease models.
• BENZOISOTHIAZOLONES AS INHIBITORS OF PHOSPHOMANNOSE ISOMERASE
  申请人：Cosford Nicholas D. P.

  公开号：US20110257233A1

  公开（公告）日：2011-10-20

  The disclosure provides new compounds and compositions thereof, and methods for treating or ameliorating a disorder relating to CDG-Ia. In particular, the disclosure provides benzoisothiazolone inhibitors of PMI, which have been synthesized and their ability to drive glycosylation has been demonstrated. The disclosure provides two synthetic routes for these compounds, including a new copper-catalyzed N-arylation reaction amenable to parallel derivitization. The disclosed compounds represent potent inhibitors of PMI, and their dose-dependent efficacy in cell-based models of glycosylation have been demonstrated. In addition, the disclosed compounds are selective over PMM and therefore, are useful in treating or ameliorating a disorder relating to CDG-Ia.
• [EN] BENZOISOTHIAZOLONES AS INHIBITORS OF PHOSPHOMANNOSE ISOMERASE<br/>[FR] BENZOISOTHIAZOLONES EN TANT QU'INHIBITEURS DE PHOSPHOMANNOSE ISOMÉRASE (PMI)
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2011116355A2

  公开（公告）日：2011-09-22

  The disclosure provides new compounds and compositions thereof, and methods for treating or ameliorating a disorder relating to CDG-Ia. In particular, the disclosure provides benzoisothiazolone inhibitors of PMI, which have been synthesized and their ability to drive glycosylation has been demonstrated. The disclosure provides two synthetic routes for these compounds, including a new copper-catalyzed N-arylation reaction amenable to parallel derivitization. The disclosed compounds represent potent inhibitors of PMI, and their dose- dependent efficacy in cell-based models of glycosylation have been demonstrated. In addition, the disclosed compounds are selective over PMM and therefore, are useful in treating or ameliorating a disorder relating to CDG-Ia.
• Ligand-free access to benzisothiazolones and benzisoselenazolones through NiFe₂O₄ catalyzed concomitant annulation of 2-halobenzanilides with chalcogens and their late-stage transformations
  作者：Samiran Dhara、Moumita Saha、Asish R. Das

  DOI：10.1039/d2nj04326b

  日期：——

  temperature and useful application of synthesized molecules. The rarely explored chemistry of NiFe2O4 towards the X–N cross-coupling reaction well complements conventional methods for the synthesis of S–N or Se–N heterocycles. Nickel ferrite nanoparticles were prepared by a simple hydrothermal method and characterized by using XRD, SEM, TEM, HRTEM, SAED, energy dispersive X-ray spectroscopy, XPS, ICP-AES and

  本工作展示了一种有效的无配体合成多种苯并异噻唑酮和苯并异硒唑酮的方法，该方法利用 X-N（X = S，Se）交叉偶联中的磁性可回收纳米镍铁氧体催化剂与 2-碘苯苯胺和元素硫或硒的同时环化. 该协议的特点是使用可回收的纳米镍铁氧体催化剂、底物多样性、廉价的硫和硒粉作为硫属化物试剂、较低的反应温度和合成分子的有用应用。NiFe 2 O 4的罕见化学X-N 交叉偶联反应很好地补充了合成 S-N 或 Se-N 杂环的常规方法。采用简单的水热法制备了镍铁氧体纳米粒子，并通过XRD、SEM、TEM、HRTEM、SAED、能量色散X射线光谱、XPS、ICP-AES和FT-IR分析对其进行了表征。催化剂易于回收和产品转化率高，使该协议具有实际经济性。使用 TBN 和氧气作为正确的氧化剂组合，苯并异噻唑酮中易氧化的硫转化为各种糖精基序。此外，含 S-N 和 Se-N 的杂环都被放大并进一步转化为新的 C-H