1-(2,6-二氯苯基)吲哚-2,3-二酮 | 24542-74-3

• 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
• 中文名称: 1-(2,6-二氯苯基)吲哚-2,3-二酮
• 英文名称: 1-(2,6-dichlorophenyl)isatin
• 英文别名: 1-(2,6-Dichlorophenyl)indole-2,3-dione
• CAS: 24542-74-3
• 化学式: C₁₄H₇Cl₂NO₂
• 分子量: 292.121
• InChiKey: MGEGDVKBXGZTRM-UHFFFAOYSA-N

物化性质

• 沸点：
  438.3±55.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

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：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

制备方法与用途

化学性质：结晶，熔点为185-187℃。

用途：作为灭酸类消炎解热镇痛药中的二氯芬酸中间体。

生产方法：通过靛红与2,6-二氯碘苯在二甲苯中反应制得。

反应信息

• 作为反应物：
  描述：

  1-(2,6-二氯苯基)吲哚-2,3-二酮 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 diclofenac sodium
  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：

  2,6-二氯-N-苯基苯胺 在 三氯化铝 作用下， 以 苯 为溶剂， 反应 22.0h， 生成 1-(2,6-二氯苯基)吲哚-2,3-二酮
  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

• Substituted phenylglycolic acid and its pharmaceutically acceptable
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04166128A1

  公开（公告）日：1979-08-28

  Novel substituted phenylglycolic acid represented by the formula ##STR1## AND ITS PHARMACEUTICALLY ACCEPTABLE NON-TOXIC ESTERS AND SALTS HAVE POTENT ANALGESIC, ANTI-INFLAMMATORY AND ANTIPYRETIC ACTIVITIES, A LOW TOXICITY AND A SATISFACTORY THERAPEUTIC INDEX, AND CAN BE FAVORABLY EMPLOYED AS A MEDICINE FOR TREATMENT OF VARIOUS INFLAMMATORY DISEASES SUCH AS ARTHRITIS, COMMON COLD, RHEUMATISM AND LIKE INFLAMMATIONS AND ALSO FOR ANALGESIC AND ANTIPYRETIC PURPOSES. The substituted phenylglycolic acid is prepared by reacting a lower alkyl ester of 2-(2,6-dichloroanilino)phenylglycolic acid with a basic substance, which lower alkyl ester is also a novel compound and can be obtained starting from 1-(2,6-dichlorophenyl)indole-2,3-dione through 2-(2,6-dichloroanilino)phenylglyoxylic acid and, in turn, a lower alkyl ester of 2-(2,6-dichloroanilino)-phenylglyoxylic acid.

  新型的取代苯基乙醇酸，化学式为##STR1##及其药用可接受的无毒酯和盐具有强效的镇痛、抗炎和退热活性，毒性低，治疗指数满意，可作为治疗各种炎症性疾病如关节炎、感冒、风湿病及类似炎症以及镇痛和退热用途的药物。取代苯基乙醇酸是通过将2-(2,6-二氯苯胺基)苯基乙醇酸的较低烷基酯与碱性物质反应制备的，这种较低烷基酯也是一种新型化合物，可以从1-(2,6-二氯苯基)吲哚-2,3-二酮出发，经过2-(2,6-二氯苯胺基)苯甘酸和依次是2-(2,6-二氯苯胺基)苯甘酸较低烷基酯获得。
• Stability of Diclofenac Sodium in the Inclusion Complex with β-Cyclodextrin in the Solid State
  作者：Barbara Cwiertnia、Teresa Hladon、Maciej Stobiecki

  DOI：10.1211/0022357991776930

  日期：2010.2.18

  The aim of this study was to characterize the thermal stability of diclofenac sodium both alone and in the inclusion complex with β-cyclodextrin in the solid state, by determination of the number of the products of its decomposition, which were identified by GC-MS.

  The molar ratio of diclofenac sodium in the inclusion complex with β-cyclodextrin was 1:1. The decomposition of diclofenac sodium both alone and in inclusion complex with β-cyclodextrin occurred according to the first-order reaction. The HPLC of the samples thermostated at 80°C gave five products of decomposition, which were identified by GC-MS.

  Diclofenac sodium in the inclusion complex with β-cyclodextrin was more thermally stable. Thermal decomposition of diclofenac sodium leads to formation of five products, of which 4-chloro-10H-9-acridinone had not been reported previously in the literature.

  本研究旨在通过GC-MS测定分解产物的数量，表征固态下双氯芬酸钠及其与β-环糊精包合物的热稳定性。

  β-环糊精包合物中双氯芬酸钠的摩尔比为1:1。双氯芬酸钠及其与β-环糊精包合物的分解均遵循一级反应。在80°C保温的样品中，HPLC检测到五种分解产物，经GC-MS鉴定。

  双氯芬酸钠与β-环糊精包合物具有更高的热稳定性。双氯芬酸钠的热分解会生成五种产物，其中4-氯-10H-9-吖啶酮在文献中尚未报道。

• Hladon, Teresa; Cwiertnia, Pharmazie, 1999, vol. 54, # 12, p. 943 - 944
  作者：Hladon, Teresa、Cwiertnia

  DOI：——

  日期：——
• JUNEK, HANS;DWORCZAK, RENATE;STERK, HEINZ;FABIAN, WALTER, LIEBIGS ANN. CHEM.,(1989) N1, C. 1065-1069
  作者：JUNEK, HANS、DWORCZAK, RENATE、STERK, HEINZ、FABIAN, WALTER

  DOI：——

  日期：——
• Junek, Hans; Dworczak, Renate; Sterk, Heinz, Liebigs Annalen der Chemie, 1989, p. 1065 - 1069
  作者：Junek, Hans、Dworczak, Renate、Sterk, Heinz、Fabian, Walter

  DOI：——

  日期：——