2,2,6-trimethylbenzo[1,3]dioxin-4-one | 300576-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2,2,6-trimethylbenzo[1,3]dioxin-4-one
• 英文别名: 2,2,6-trimethyl-4H-benzo[d][1,3]dioxin-4-one；2,2,6-trimethyl-1,3-benzodioxin-4-one
• CAS: 300576-29-8
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: GFKJJASMZFMMCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,6-trimethylbenzo[1,3]dioxin-4-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以78%的产率得到6-(dibromomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one
  参考文献：
  名称：

  A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

  摘要：

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.030
• 作为产物：
  描述：

  5-甲基水杨酸 在 氯化亚砜 作用下， 生成 2,2,6-trimethylbenzo[1,3]dioxin-4-one
  参考文献：
  名称：

  An approach to the identification of potent inhibitors of influenza virus fusion using parallel synthesis methodology

  摘要：

  Structure-activity studies associated with the salicylic acid-derived inhibitor of influenza fusion, BMY-27709, were examined using a parallel synthesis approach. This SAR survey led to the discovery of potent influenza inhibitory activity in a series of aromatic amides and thioamides derived from 1,3,3-trimethyl-5-hydroxycyclohexylmethylamine. Select compounds were characterized as inhibitors of the HI subtype of influenza A viruses that act by preventing the pl-l-induced fusion process, thereby blocking viral entry into host cells. In a plaque-reduction assay, the most potent inhibitors displayed EC50 values of 0.02-0.14 mug/mL. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00459-0

文献信息

• Compounds and their Salts Specific to the PPAR Receptors and the EGF Receptors and their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20120316230A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds of formula (I), where R 1 and R 2 , which may be identical or different, are selected from the group comprising H, C n H 2n-1 , a linear or branched alkyl group having 1 to 6 carbons, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R 3 is —CO—CH 3 , —NHOH, —OH, or —OR 6 where R 6 is a linear or branched alkyl group having 1 to 6 carbon atoms; R4 is H, linear or branched alkyl group having from 1 to 6 atoms, phenyl, benzyl, —CF 3 or CF 2 CF 3 , vinyl or allyl; R 5 , R 7 , R 8 are hydrogen atoms; or R 3 and R 4 , R 4 and R 5 , or R 7 and R 8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  本发明涉及式（I）的化合物，其中R1和R2，可以相同也可以不同，选择自H，CnH2n-1，具有1至6个碳的线性或支链烷基团，或者共同形成一个具有5或6个原子的芳香或脂肪环；R3为—CO—CH3，—NHOH，—OH或—OR6，其中R6为具有1至6个碳的线性或支链烷基团；R4为H，具有1至6个原子的线性或支链烷基团，苯基，苄基，—CF3或CF2CF3，乙烯基或丙烯基；R5，R7，R8为氢原子；或者R3和R4，R4和R5，或R7和R8共同形成一个环，与苯环，芳香或脂肪环共同构成一个具有1至2个杂原子的环，独立选择自N，O的群组；以及在医药领域中的应用。
• Development of hetero-triaryls as a new chemotype for subtype-selective and potent Sirt5 inhibition
  作者：Carina Glas、Eli Naydenova、Severin Lechner、Nathalie Wössner、Liu Yang、Johannes C.B. Dietschreit、Hongyan Sun、Manfred Jung、Bernhard Kuster、Christian Ochsenfeld、Franz Bracher

  DOI：10.1016/j.ejmech.2022.114594

  日期：2022.10

  In contrast to other sirtuins (NAD+-dependent class III lysine deacylases), inhibition of Sirt5 is poorly investigated, yet. Our present work is based on the recently identified Sirt5 inhibitor balsalazide, an approved drug with negligible bioavailability after oral administration. After gaining first insights into its structure-activity relationship in previous work, we were able to now develop heteroaryl-triaryls

  与其他去乙酰化酶（NAD +依赖性 III 类赖氨酸脱酰基酶）相比，Sirt5 的抑制作用尚未得到很好的研究。我们目前的工作基于最近发现的 Sirt5 抑制剂巴柳氮，这是一种经批准的药物，口服后生物利用度可忽略不计。在之前的工作中首次了解其构效关系后，我们现在能够开发出杂芳基-三芳基化合物作为一种新型化学类型的药物样、强效和亚型选择性 Sirt5 抑制剂。铅结构的不利偶氮基团以系统和全面的方式进行了修饰，使我们得到了一些开链，最重要的是，五元杂环取代物（异恶唑CG_209、三唑CG_220、吡唑CG_232) 具有非常令人鼓舞的体外活性（Sirt5 上的 IC 50在低微摩尔范围内，<10 μM）。这些先进的抑制剂没有细胞毒性，并显示出良好的药代动力学特性，这通过活细胞成像实验对线粒体的渗透性得到了证实。此外，与作为参考化合物的巴柳氮相比，计算类似物的相对游离结合亲和力的结果与体外获得的抑
• Salicylamide inhibitors of influenza virus fusion
  作者：Keith D. Combrink、H.Belgin Gulgeze、Kuo-Long Yu、Bradley C. Pearce、Ashok K. Trehan、Jianmei Wei、Milind Deshpande、Mark Krystal、Albert Torri、Guangxiang Luo、Christopher Cianci、Stephanie Danetz、Laurence Tiley、Nicholas A. Meanwell

  DOI：10.1016/s0960-894x(00)00335-8

  日期：2000.8

  Structural variation of the quinolizidine heterocycle of the influenza fusion inhibitor BMY-27709 was examined by several topological dissections in order to illuminate the critical features of the ring system. This exercise resulted in the identification of a series of synthetically more accessible decahydroquinolines that retained the structural elements of BMY-27709 important for antiviral activity. The 2-methyl-cis-decahydroquinoline 6f was the most potent influenza inhibitor identified that demonstrated an EC50 of 90 ng/mL in a plaque reduction assay. (C) 2000 Elsevier Science Ltd. All rights reserved.
• COMPOUND FOR THE TREATMENT OF PSORIASIS
  申请人：Nogra Pharma Limited

  公开号：EP2355810B1

  公开（公告）日：2017-07-12
• US8138357B2
  申请人：——

  公开号：US8138357B2

  公开（公告）日：2012-03-20