3-(2-aminoethyl)-5-methoxy-2-methylindolyl 4-chlorophenyl ketone

• 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: 3-(2-aminoethyl)-5-methoxy-2-methylindolyl 4-chlorophenyl ketone
• 英文别名: 3-(2-Aminoethyl)-5-methoxy-2-methylindolyl 4-chlorophenyl ketone hydrochloride；[3-(2-aminoethyl)-5-methoxy-2-methylindol-1-yl]-(4-chlorophenyl)methanone
• 化学式: C₁₉H₁₉ClN₂O₂
• 分子量: 342.825
• InChiKey: AZIINBAVIXTVNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-aminoethyl)-5-methoxy-2-methylindolyl 4-chlorophenyl ketone 在 甲烷磺酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING

  摘要：

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。

  公开号：

  US20150374858A1
• 作为产物：
  描述：

  吲哚美辛酰胺 在 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-(2-aminoethyl)-5-methoxy-2-methylindolyl 4-chlorophenyl ketone
  参考文献：
  名称：

  CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING

  摘要：

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。

  公开号：

  US20150374858A1

文献信息

• Structure-Based Design, Synthesis, and Biological Evaluation of Indomethacin Derivatives as Cyclooxygenase-2 Inhibiting Nitric Oxide Donors
  作者：Shiow-Jyi Wey、Michael E. Augustyniak、Edward D. Cochran、James L. Ellis、Xinqin Fang、David S. Garvey、David R. Janero、L. Gordon Letts、Allison M. Martino、Terry L. Melim、Madhavi G. Murty、Steward K. Richardson、Joseph D. Schroeder、William M. Selig、A. Mark Trocha、Roseanne S. Wexler、Delano V. Young、Irina S. Zemtseva、Brian M. Zifcak

  DOI：10.1021/jm0611861

  日期：2007.12.13

  Indomethacin, a nonselective cyclooxygenase (COX) inhibitor, was modified in three distinct regions in an attempt both to increase cyclooxygenase-2 (COX-2) selectivity and to enhance drug safety by covalent attachment of an organic nitrate moiety as a nitric oxide donor. A human whole-blood COX assay shows the modifications on the 3-acetic acid part of the indomethacin yielding an amide-nitrate derivative 32 and a sulfonamide-nitrate derivative 61 conferred COX-2 selectivity. Along with their respective des-nitrate analogs, for example, 31 and 62, the nitrates 32 and 61 were effective antiinflammatory agents in the rat air-pouch model. After oral dosing, though, only 32 increased nitrate and nitrite levels in rat plasma, indicating that its nitrate tether served as a nitric oxide donor in vivo. In a rat gastric injury model, examples 31 and 32 both show a 98% reduction in gastric lesion score compared to that of indomethacin. In addition, the nitrated derivative 32 inducing 85% fewer gastric lesions when coadministered with aspirin as compared to the combination of aspirin and valdecoxib.
• US9850183B2
  申请人：——

  公开号：US9850183B2

  公开（公告）日：2017-12-26
• [EN] CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING<br/>[FR] CONJUGUES DERIVES DE MEDICAMENTS ANTI-INFLAMMATOIRES NON STEROIDIENS ET PROCEDES D'UTILISATION DE CEUX-CI DANS L'IMAGERIE
  申请人：REILEY PHARMACEUTICALS INC

  公开号：WO2015200187A1

  公开（公告）日：2015-12-30

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.
• CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING
  申请人：Reiley Pharmaceuticals, Inc.

  公开号：US20150374858A1

  公开（公告）日：2015-12-31

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。