[o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid | 23189-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid
• 英文别名: -essigsaeure；[o-(6-Chlor-o-toluidino)-phenyl]-essigsaeure；[o-(3-Chloro-o-toluidino)-phenyl]-acetic acid；2-[2-(2-chloro-6-methylanilino)phenyl]acetic acid
• CAS: 23189-28-8
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: PQOGEFXKUUCLAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid 、 重氮甲烷 在 乙醚 、 碳酸氢钠 、 水 、 Sodium sulfate-III 、 苯 作用下， 以 乙醚 为溶剂， 25.0~40.0 ℃ 、195.52 kPa 条件下， 反应 2.0h， 生成 [o-(6-chloro-o-toluidino)-phenyl]-acetic acid methyl ester
  参考文献：
  名称：

  Antiphlogistic phenylacetohydroxamic acid compositions

  摘要：

  公式I的苯乙酰羟肟酸，其中R.sub.1，R.sub.2，R.sub.3和R.sub.4独立地表示氢，氯，氟或溴原子或具有最多6个碳原子的烷基或烷氧基，其中R.sub.2还可以表示三氟甲基基团，前提是R.sub.1，R.sub.2和R.sub.3不能同时表示氢原子，并且它们与碱的药物可接受的盐，这些化合物抑制血小板聚集并表现出有价值的药理学特性，特别是抗炎，镇痛和退烧活性。

  公开号：

  US04092430A1
• 作为产物：
  描述：

  [o-(3-Chloro-o-toluidino)-phenyl]-glyoxylic acid 在 sodium methylate 、 一水合肼 作用下， 以 乙二醇甲醚 为溶剂， 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
• 作为试剂：
  描述：

  钠 、 [o-(3-Chloro-o-toluidino)-phenyl]-glyoxylic acid 、 一水合肼 、 sodium methylate 在 乙二醇乙醚 、 水 、 乙醚 、 乙酸乙酯 、 Sodium sulfate-III 、 [o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid 作用下， 以 乙醇 为溶剂， 30.0~150.0 ℃ 、195.52 kPa 条件下， 反应 0.08h， 生成 [o-(2-methyl-6-chloro-anilino)-phenyl]-acetic acid
  参考文献：
  名称：

  Phenylacetohydroxamic acids

  摘要：

  具有I式的苯乙酰羟胺酸，其中R1，R2，R3和R4独立地表示氢，氯，氟或溴原子或具有最多6个碳原子的烷基或烷氧基，其中R2还可以表示三氟甲基基团，但R1，R2和R3不能同时表示氢原子，以及它们与碱的药学上可接受的盐。这些化合物抑制血小板聚集并表现出有价值的药理学，特别是抗炎，镇痛和退热活性。

  公开号：

  US04173577A1

文献信息

• Analgesic and anti-inflammatory anilino-phenylacetic acid-(2,3 or 4
  申请人：Ciba-Geigy Corporation

  公开号：US03973024A1

  公开（公告）日：1976-08-03

  Basic esters and acid addition salts thereof of substituted o-anilino-phenylacetic acids with pyridinols or pyridine-alkanols have anti-inflammatory and analgesic activity; they are active ingredients of pharmaceutical compositions and can be used for the relief and removal of pain as well as for the treatment of rheumatic, arthritic and other inflammatory complaints; an illustrative example is [o-(2,6-Dichloro-anilino)-phenyl]-acetic acid (2-pyridyl)-methyl ester.

  被取代的o-苯胺基乙酸酯与吡啶醇或吡啶-烷醇的酸加成盐具有抗炎和镇痛活性；它们是药物组成的活性成分，可用于缓解和消除疼痛以及治疗风湿性、关节炎和其他炎症疾病；一个例子是[o-(2,6-二氯苯氨基)-苯基]-乙酸(2-吡啶基)-甲酯。
• 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.

  公式I的苯乙酰羟肟酸，其中R.sub.1，R.sub.2，R.sub.3和R.sub.4独立地表示氢，氯，氟或溴原子或具有最多6个碳原子的烷基或烷氧基，其中R.sub.2还可以表示三氟甲基基团，前提是R.sub.1，R.sub.2和R.sub.3不能同时表示氢原子，并且它们与碱的药物可接受的盐，这些化合物抑制血小板聚集并表现出有价值的药理学特性，特别是抗炎，镇痛和退烧活性。
• Identification of Stabilizers of Multimeric Proteins
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20150126532A1

  公开（公告）日：2015-05-07

  Disclosed herein are compounds and compositions thereof which find use in increasing stability of TTR tetramers reducing its tendency to misfold and form aggregates. Also provided herein are methods for using these compounds and compositions for increasing stability of TTR and thereby decreasing aggregate formation by TTR. Also disclosed herein are methods to screen for candidate compounds that increase stability of TTR. Also disclosed herein are heterobifunctional compounds that include a TTR binding compound connected to a targeting moiety via a linker, for use in disrupting PPIs of a target protein.

  本文公开了一些化合物及其组合物，可用于增加TTR四聚体的稳定性，减少其错折和聚集的倾向。本文还提供了使用这些化合物和组合物增加TTR稳定性、从而减少TTR聚集形成的方法。本文还公开了筛选候选化合物以增加TTR稳定性的方法。本文还公开了异双功能化合物，其中包括一个TTR结合化合物通过连接子连接到一个靶向基团上，用于破坏目标蛋白质的蛋白质相互作用。
• SYSTEMS, DEVICES, AND METHODS FOR PASSIVE TRANSDERMAL DELIVERY OF ACTIVE AGENTS TO A BIOLOGICAL INTERFACE
  申请人：Nomoto Youhei

  公开号：US20080286349A1

  公开（公告）日：2008-11-20

  Systems, devices, and methods for transdermal delivery of one or more therapeutic active agents to a biological interface. A transdermal drug delivery system is provided for passive transdermal delivery of one or more ionizable active agents to a biological interface of a subject. A transdermal drug delivery system includes a backing substrate, and an active agent layer. The active layer includes a thickening agent, a plasticizer, and a therapeutically effective amount of an ionizable active agent.
• PET MONITORING OF A-BETA-DIRECTED IMMUNOTHERAPY
  申请人：Black Ronald

  公开号：US20130084245A1

  公开（公告）日：2013-04-04

  The present invention provides methods of monitoring Aβ-directed immunotherapy. The methods involve administering a PET ligand that binds to amyloid deposits and detecting the PET ligand in the brain to provide an indication of the level and/or distribution of amyloid deposits. Surprisingly, the data in the present application show that a statistically significant reduction in amyloid deposits occurs early and consistently among patients following initiation of treatment before statistically significant effects of most if not all other markers are detectable. In consequence, the present methods allow early detection of whether a patient is responding to the Aβ-directed immunotherapy and if necessary adjustment of the immunotherapy regime.