2-[2-(3-bromophenyl)-2-oxoethyl]-1,2-benzothiazol-3(2H)-one 1,1-dioxide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-(3-bromophenyl)-2-oxoethyl]-1,2-benzothiazol-3(2H)-one 1,1-dioxide
• 英文别名: 2-[2-(3-bromophenyl)-2-oxoethyl]-1,1-dioxo-1,2-benzothiazol-3-one
• 化学式: C₁₅H₁₀BrNO₄S
• 分子量: 380.219
• InChiKey: YASUVFLTLOHPIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(3-bromophenyl)-2-oxoethyl]-1,2-benzothiazol-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 (3-bromo-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
• 作为产物：
  描述：

  saccharin sodium salt 、 2,3-二溴苯乙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以76%的产率得到2-[2-(3-bromophenyl)-2-oxoethyl]-1,2-benzothiazol-3(2H)-one 1,1-dioxide
  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