2-(9H-carbazol-2-yl)propanoic acid | 52263-68-0

• 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: 2-(9H-carbazol-2-yl)propanoic acid
• 英文别名: 2-carbazol-2-yl-propionic acid
• CAS: 52263-68-0
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: HSJIVJPREZQHFK-UHFFFAOYSA-N

物化性质

• 沸点：
  481.7±20.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  卡洛芬 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以40%的产率得到2-(9H-carbazol-2-yl)propanoic acid
  参考文献：
  名称：

  Identification and Characterization of Carprofen as a Multitarget Fatty Acid Amide Hydrolase/Cyclooxygenase Inhibitor

  摘要：

  Pain and inflammation are major therapeutic areas for drug discovery. Current drugs for these pathologies have limited efficacy, however, and often cause a number of unwanted side effects. In the present study, we identify the nonsteroidal anti-inflammatory drug carprofen as a multitarget-directed ligand that simultaneously inhibits cyclooxygenase-1 (COX-1), COX-2, and fatty acid amide hydrolase (FAAH). Additionally, we synthesized and tested several derivatives of carprofen, sharing this multitarget activity. This may result in improved analgesic efficacy and reduced side effects (Naidu et al. J. Pharmacol. Exp. Ther. 2009, 329, 48-56; Fowler, C. J.; et al. J. Enzyme Inhib. Med. Chem. 2012, in press; Sasso et al. Pharmacol. Res. 2012, 65, 553). The new compounds are among the most potent multitarget FAAH/COX inhibitors reported so far in the literature and thus may represent promising starting points for the discovery of new analgesic and anti-inflammatory drugs.

  DOI：

  10.1021/jm3011146

文献信息

• Total synthesis of carbazole alkaloids
  作者：Bharath kumar goud Bhatthula、Janardhan reddy Kanchani、Veera reddy Arava、M.C.S. Subha

  DOI：10.1016/j.tet.2019.01.003

  日期：2019.2

  Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-

  Suzuki-Miyaura交叉偶联，然后是三苯基膦介导的Cadogan还原环化序列，提供了对一系列咔唑生物碱的有效利用。 在目前的工作中，该方法已应用于总的合成，其中包括穆科宁，clauszoline K，koenoline，murrayanine，murrayafoline A，mukoeic acid，glycorborine，glycolzolicine，mukolidine，mukoline，glycozoline，3-甲氧基-9 H-咔唑-1-羧酸甲酯，（3-甲氧基-9 H-咔唑-1-基）-甲醇，3-甲氧基-9 H-咔唑-1-甲醛，3-甲氧基-9 H-咔唑-1-羧酸，2 -甲基-9 H-咔唑和非甾体抗炎药（NSAID）卡洛芬及其衍生物。
• CONTROL RELEASE OF BIOLOGICALLY ACTIVE COMPOUNDS FROM MULTI-ARMED OLIGOMERS
  申请人：Bezwada Rao S.

  公开号：US20090076174A1

  公开（公告）日：2009-03-19

  The present invention relates to the discovery of biodegradable multi-armed oligomers wherein the end groups of these oligomers have been functionalized with biologically active molecules. The resultant multi-armed oligomers end-functionalized with biologically active molecules have a controllable degradation profile. The hydrolytic degradation of oligomers of the present invention releases the biologically active compound as such with no change in native chemical structure.

  本发明涉及可生物降解的多臂寡聚体的发现，其中这些寡聚体的末端基团已经被生物活性分子功能化。末端功能化生物活性分子的多臂寡聚体具有可控的降解特性。本发明的寡聚体的水解降解会释放出生物活性化合物，其原有的化学结构不会发生改变。
• Verfahren zur Herstellung eines Carbazolderivates
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0151423A2

  公开（公告）日：1985-08-14

  Neue Verbindungen der Formel worin R Wasserstoff, Acetyl oder Propionyl und Q Acetyl ist oder R Wasserstoff und 0 C(H,CH3)OC(O)R2 oder C(CN,CH3)OSi(R3,R4,R5) ist, worin R2 Wasserstoff, C1-10-Alkyl, C2-10-Alkenyl, C4-7-Cycloalkyl, Aryl oder eine 5- oder 6- gliedrige heterocyclische Gruppe ist, und R3, R4 und R5 geradkettige C1-4-Alkylgruppen sind, ihre Herstellung aus 2-Acetyl-carbazolen und ihre Verwendung zur Herstellung der 6-Chlor-a-methylcarbazol-2-essigsäure.

  式中 R 为氢、乙酰基或丙酰基且 Q 为乙酰基，或 R 为氢且 0 为 C(H,CH3)OC(O)R2，或 C(CN,CH3)OSi(R3,R4,R5)的新化合物，其中 R2 为氢、C1-10 烷基、C2-10 烯基、C4-7 环烷基、芳基或 5 或 6 元杂环基团，R3、R4 和 R5 为直链 C1-4 烷基，它们由 2-乙酰基咔唑制备，并用于制备 6-氯-a-甲基咔唑-2-乙酸。
• Drug delivery system for hydrophobic drugs
  申请人：QLT, Inc.

  公开号：EP1900357A2

  公开（公告）日：2008-03-19

  Compositions comprising microaggregates containing hydrophobic drugs, as well as methods for their production, are described. Such microaggregates may include micelle structures or combinations thereof with liposomes, and constitute an effective delivery vehicle for a hydrophobic agent. Methods for microaggregate production include the use of preferred lipid compounds and processing conditions favoring the production of small aggregates for improved filter sterilization.

  本文介绍了由含有疏水性药物的微团聚体组成的组合物及其生产方法。这种微团聚体可包括胶束结构或其与脂质体的组合，并构成疏水性药物的有效递送载体。微团聚体的生产方法包括使用优选的脂质化合物和有利于生产小团聚体的加工条件，以提高过滤灭菌效果。
• Immuno-adjuvant PDT treatment of metastatic tumors
  申请人：——

  公开号：US20020022032A1

  公开（公告）日：2002-02-21

  Immuno-adjuvant photodynamic therapy to treat and prevent metastatic cancer is effected using photosensitizers in combination with immuno-adjuvants to destroy metastatic tumor cells.

  治疗和预防转移性癌症的免疫辅助光动力疗法是利用光敏剂与免疫辅助剂相结合来破坏转移性肿瘤细胞。