(3-fluoro-phenyl)-(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-2H-benzo[e][1,2]thiazin-3-yl)-methanone | 1242134-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3-fluoro-phenyl)-(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-2H-benzo[e][1,2]thiazin-3-yl)-methanone
• CAS: 1242134-18-4
• 化学式: C₁₆H₁₂FNO₄S
• 分子量: 333.34
• InChiKey: BUXTXVBDARCZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  23.0
• 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

• 作为产物：
  描述：

  3-氟溴代苯乙酮 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (3-fluoro-phenyl)-(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-2H-benzo[e][1,2]thiazin-3-yl)-methanone
  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

文献信息

• DERIVATIVES OF BENZOTHIAZINES, PREPARATION THEREOF AND APPLICATION THEREOF AS DRUGS
  申请人：Perez Michel

  公开号：US20110319326A1

  公开（公告）日：2011-12-29

  The object of the present invention is benzothiazine derivatives having the capability of inhibiting 11β-HSD1 not only at an enzymatic level but also at a cell level. The compounds of the present invention are of general formula (I). Wherein notably R 1 represents a hydrogen or OR1 represents an ester or an ether. R 2 represents a naphthyl or a 1, 2, 3, 4-tetrahydro-naphthalene or a biphenyl or phenyl pyridine or a substituted phenyl. R 3 represents a methyl or ethyl; R 4 and R′ 4 represent a hydrogen.

  本发明的目的是提供能够在酶水平和细胞水平上抑制11β-HSD1的苯并噻嗪衍生物。本发明的化合物具有一般式（I），其中特别地，R1表示氢或OR1表示酯或醚，R2表示萘基或1,2,3,4-四氢萘基或联苯基或苯基吡啶或取代苯基，R3表示甲基或乙基，R4和R′4表示氢。
• US9187438B2
  申请人：——

  公开号：US9187438B2

  公开（公告）日：2015-11-17