2-(2-methylphenoxy)-5-nitrobenzoic acid | 291781-19-6

• 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: 2-(2-methylphenoxy)-5-nitrobenzoic acid
• 英文别名: 5-nitro-2-o-tolyloxy-benzoic acid；5-Nitro-2-o-tolyloxy-benzoesaeure；o-Tolylaether-5-nitro-salicylsaeure
• CAS: 291781-19-6
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: ARXXJUMMADZEQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-methylphenoxy)-5-nitrobenzoic acid 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 作用下， 以 四氯化碳 为溶剂， 生成 5-nitro-2-(2-bromomethylphenoxy)-benzoic acid methyl ester
  参考文献：
  名称：

  Zhuang; Choi; Hou, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S357-S359

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 、 邻甲酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到2-(2-methylphenoxy)-5-nitrobenzoic acid
  参考文献：
  名称：

  取代乙基 4-羟基-11-氧代-11 H - chromeno[2,3-g]quinoline-3-carboxylates 的合成及抗球虫活性

  摘要：

  设计合成了一系列作为抗球虫药的取代乙基4-羟基-11-氧代-11H-色诺[2,3-g]喹啉-3-羧酸酯，并通过1H NMR、MS、IR光谱和基本分析。根据抗球虫指数法评估新化合物的抗球虫活性。结果表明，这些化合物中的四种在鸡日粮中以 27 mg kg-1 的剂量显示出对艾美球虫的有效抗球虫活性。

  DOI：

  10.3184/174751911x13090888724310

文献信息

• SPECT imaging agents for serotonin transporters
  申请人：Kung Hank F.

  公开号：US06921840B1

  公开（公告）日：2005-07-26

  The present invention is directed to compounds of Formula (I) or pharmaceutically acceptable salts thereof; wherein X is hydrogen, Cl, Br, I, NO 2 , NR 3 R 4 or —L—Ch; Y is hydrogen, —CH 2 OR 5 , —CH 2 NCH 3 R 1 , NO 2 , NR 3 R 4 or —L—Ch; Y′ is hydrogen, —CH 2 OH 5 , —CH 2 NCH 3 R 1 , NO 2 , NR 3 R 4 OR —L—Ch; provided that at least one of the Y or Y′ is —CH 2 NCH 3 R 1 ; Z is S, O, NR 6 CR 7 R 8 , C(O) or —C(═CR 7 R 8 )-; A is hydrogen, Cl, I, Br or —L—Ch; R 1 is hydrogen, C 1 -C 5 alkyl, C 3 -C 8 cycloalkyl C 1-5 alkylcarbonyl, (C 3 -C 8 cycloalkyl) carbonyl, pnenyl, benzyl, naphthyl, naphthylmethyl or L—Ch; R 2 is hydrogen or methyl; and R 3 -R 8 are as defined herein. Radiolabeled compounds of the invention are useful as selective serotonin transporter (SERT) imaging agents for single photon emission tomography (SPECT). As such the compounds are useful for studying the underlying pharmacology and interaction of specific serotinin reuptake site inhibitors (SSRI), commonly used antidepressants, at the SERT sites in the human brain. Certain compounds of the invention, including IDAM (5-iodo-2[[2-2-[(dimethylamino)methyl]phenyl]thio]benzylalcohol) display affinity to SERT sites and show more high selectively for SERT over NET and DAT.

  本发明涉及化合物的公式（I）或其药用盐；其中X为氢，Cl，Br，I，NO2，NR3R4或—L—Ch；Y为氢，—CH2OR5，—CH2NCH3R1，NO2，NR3R4或—L—Ch；Y′为氢，—CH2OH5，—CH2NCH3R1，NO2，NR3R4或—L—Ch；但要求Y或Y′中至少有一个为—CH2NCH3R1；Z为S，O，NR6CR7R8，C(O)或—C(═CR7R8)-；A为氢，Cl，I，Br或—L—Ch；R1为氢，C1-C5烷基，C3-C8环烷基，C1-5烷基羰基，（C3-C8环烷基）羰基，苯基，苄基，萘基，萘甲基或L—Ch；R2为氢或甲基；R3-R8如本文所定义。本发明的放射标记化合物可用作选择性血清素转运蛋白（SERT）成像剂，用于单光子发射断层扫描（SPECT）。因此，这些化合物可用于研究在人类大脑中SERT位点处特定血清素再摄取抑制剂（SSRI）的药理学和相互作用。本发明的某些化合物，包括IDAM（5-碘-2[[2-2-[(二甲氨基)甲基]苯基]硫基]苄醇），对SERT位点显示亲和力，并且对SERT比NET和DAT具有更高的选择性。
• EP1175388A4
  申请人：——

  公开号：EP1175388A4

  公开（公告）日：2003-06-18
• SPECT IMAGING AGENTS FOR SEROTONIN TRANSPORTERS
  申请人：TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：EP1175388A1

  公开（公告）日：2002-01-30
• US6921840B1
  申请人：——

  公开号：US6921840B1

  公开（公告）日：2005-07-26
• [EN] SPECT IMAGING AGENTS FOR SEROTONIN TRANSPORTERS<br/>[FR] AGENTS D'IMAGERIE DESTINES A LA TOMOGRAPHIE MONOPHOTONIQUE D'EMISSION POUR TRANSPORTEURS DE SEROTONINE
  申请人：KUNG HANK F

  公开号：WO2000066537A1

  公开（公告）日：2000-11-09

  The present invention is directed to compounds of Formula (I) or pharmaceutically acceptable salts thereof; wherein X is hydrogen, C1, Br, I, NO2, NR3R4 or -L-Ch; Y is hydrogen, -CH¿2?OR?5, -CH¿2NCH3R1, NO2, NR3R4 or -L-Ch; Y' is hydrogen, -CH¿2?OR?5, -CH¿2NCH3R1, NO2, NR3R4 OR -L-Ch; provided that at least one of the Y or Y' is -CH¿2NCH3R?1; Z is S, O, NR?6, CR7R8¿, C(O) or -C(=CR7R8)-; A is hydrogen, C1, I, Br or -L-Ch; R1 is hydrogen, C¿1?-C5 alkyl, C3-C8 cycloalkyl C1-5 alkylcarbonyl, (C3-C8 cycloalkyl) carbonyl, pnenyl, benzyl, naphthyl, naphthlymethyl or L-Ch; R?2¿ is hydrogen or methyl; and R3-R8 are as defined herein. Radiolabeled compounds of the invention are useful as selective serotonin transporter (SERT) imaging agents for single photon emission tomography (SPECT). As such the compounds are useful for studying the underlying pharmacology and interaction of specific serotinin reuptake site inhibitors (SSRI), commonly used antidepressants, at the SERT sites in the human brain. Certain compounds of the invention, including IDAM (5-iodo-2[[2-2-[(dimethylamino)methyl]phenyl]thio]benzylalcohol) display ecxellent affinity to SERT sites and show more high selectively for SERT over NET and DAT.