1-(3-chloro-o-tolyl)-indole-2,3-dione | 24542-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-chloro-o-tolyl)-indole-2,3-dione
• 英文别名: 1-(2-Chloro-6-methylphenyl)indole-2,3-dione
• CAS: 24542-73-2
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: RXIDIZBGWVLYIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-chloro-o-tolyl)-indole-2,3-dione 在 sodium hydroxide 、 sodium methylate 、 一水合肼 作用下， 以 乙醇 、 乙二醇甲醚 、 水 为溶剂， 反应 1.17h， 生成 [o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.

  DOI：

  10.1021/jm00171a008
• 作为产物：
  描述：

  (2-chloro-6-methyl)diphenylamine 在 三氯化铝 作用下， 以 苯 为溶剂， 反应 22.0h， 生成 1-(3-chloro-o-tolyl)-indole-2,3-dione
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of diclofenac analogs

  摘要：

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.

  DOI：

  10.1021/jm00171a008

文献信息

• Antiphlogistic phenylacetohydroxamic acid compositions
  申请人：Ciba-Geigy Corporation

  公开号：US04092430A1

  公开（公告）日：1978-05-30

  Phenylacetohydroxamic acids having the formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of each other, represent hydrogen, chlorine, fluorine or bromine atoms or an alkyl or alkoxy group having at most 6 carbon atoms, and wherein R.sub.2 may additionally represent a trifluoromethyl group with the proviso that R.sub.1, R.sub.2 and R.sub.3 may not simultaneously represent hydrogen atoms and their pharmaceutically acceptable salts with bases, which compounds inhibit plateletaggregation and exhibit valuable pharmacological, in particular, antiphlogistic, analgesic and antipyretic activity.

  具有以下结构式的苯乙酰羟肟酸I，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4分别独立地表示氢、氯、氟或溴原子或最多具有6个碳原子的烷基或烷氧基，并且其中R.sub.2还可以表示三氟甲基，但要求R.sub.1、R.sub.2和R.sub.3不能同时表示氢原子，以及它们与碱形成的药用可接受盐，这些化合物抑制血小板聚集并表现出有价值的药理活性，特别是抗炎、镇痛和退热活性。
• US4092430A
  申请人：——

  公开号：US4092430A

  公开（公告）日：1978-05-30
• US4173577A
  申请人：——

  公开号：US4173577A

  公开（公告）日：1979-11-06
• Synthesis and quantitative structure-activity relationships of diclofenac analogs
  作者：Peter Moser、Alfred Sallmann、Irmgard Wiesenberg

  DOI：10.1021/jm00171a008

  日期：1990.9

  The synthesis of a series of 2-anilinophenylacetic acids, close analogues of diclofenac, is described. These compounds were tested in two models used for evaluating the activity of nonsteroidal antiinflammatory drugs (NSAID's), inhibition of cyclooxygenase enzyme activity in vitro, and adjuvant-induced arthritis (AdA) in rats. Statistically significant correlations were found between the inhibitory activities of the compounds in these two models, indicating that cyclooxygenase inhibition seems to be the underlying mechanism for the antiinflammatory activity of these compounds. Quantitative structure-activity relationship (QSAR) analysis revealed that the crucial parameters for activity in both models were the lipophilicity and the angle of twist between the two phenyl rings. Optimal activities were associated with halogen or alkyl substituents in both ortho positions of the anilino ring. Compounds with OH groups in addition to two ortho substituents or compounds with only one or no ortho substituents were less active.