2-(6-chloro-9-methyl-9H-carbazol-2-yl)propanoic acid | 52263-56-6

• 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-(6-chloro-9-methyl-9H-carbazol-2-yl)propanoic acid
• 英文别名: 2-(6-chloro-9-methylcarbazol-2-yl)propanoic acid
• CAS: 52263-56-6
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: UMFUSWPRRINICR-UHFFFAOYSA-N

物化性质

• 沸点：
  425.6±43.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(6-chloro-9-methyl-9H-carbazol-2-yl)propanoic acid 在 potassium tert-butylate 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 69.0h， 生成
  参考文献：
  名称：

  α-羰基磺叶立德在芳基和杂芳基上的化学特异性环化

  摘要：

  尽管亚砜叶立德具有有利的安全性，但在没有导向基团帮助的情况下使用α-羰基亚砜叶立德对芳基和杂芳基进行官能化迄今为止仍然是一个被忽视的领域。本文描述了在 HFIP 中碱存在下，α-羰基亚锍叶立德在苯、苯并呋喃和 N-对甲苯磺酰吲哚上的环化，而吡咯和N-甲基吲哚在铱催化剂存在下进行环化。值得注意的是，这两组条件对于每组底物都是化学特异性的。

  DOI：

  10.1002/anie.201910821
• 作为产物：
  描述：

  卡洛芬 在 硫酸 、 水 、 caesium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 36.0h， 生成 2-(6-chloro-9-methyl-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

• Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines
  作者：Sebastiano Ortalli、Joseph Ford、Andrés A. Trabanco、Matthew Tredwell、Véronique Gouverneur

  DOI：10.1021/jacs.4c02474

  日期：——

  TEMPO-derived alkoxyamines, a class of substrates accessible in a single step from a diversity of readily available carboxylic acids, halides, alkenes, alcohols, aldehydes, boron reagents, and C–H bonds. This mild and versatile one-electron pathway affords radiolabeled aliphatic fluorides that are typically inaccessible applying conventional nucleophilic substitution technologies due to insufficient reactivity

  在此，我们报道了使用 TEMPO 衍生的烷氧基胺进行光氧化还原亲核（放射性）氟化，这是一类底物，可通过多种容易获得的羧酸、卤化物、烯烃、醇、醛、硼试剂和 C-H 一步获得债券。这种温和且通用的单电子途径提供了放射性标记的脂肪族氟化物，由于反应性不足和竞争性消除，应用传统的亲核取代技术通常无法获得这些氟化物。该光氧化还原过程的自动化还通过用户友好且市售的光氧化还原流反应器和放射合成平台进行了演示，因此加快了获得高摩尔活性 ( A m ) 的标记脂肪族氟化物的速度，以进行临床（前）评估。
• Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
  作者：Daniel Clare、Benjamin C. Dobson、Phillip A. Inglesby、Christophe Aïssa

  DOI：10.1002/anie.201910821

  日期：2019.11.4

  The functionalization of aryl and heteroaryls using α‐carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α‐carbonyl sulfoxonium ylides onto benzenes, benzofurans and N‐p‐toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles

  尽管亚砜叶立德具有有利的安全性，但在没有导向基团帮助的情况下使用α-羰基亚砜叶立德对芳基和杂芳基进行官能化迄今为止仍然是一个被忽视的领域。本文描述了在 HFIP 中碱存在下，α-羰基亚锍叶立德在苯、苯并呋喃和 N-对甲苯磺酰吲哚上的环化，而吡咯和N-甲基吲哚在铱催化剂存在下进行环化。值得注意的是，这两组条件对于每组底物都是化学特异性的。
• Identification and Characterization of Carprofen as a Multitarget Fatty Acid Amide Hydrolase/Cyclooxygenase Inhibitor
  作者：Angelo D. Favia、Damien Habrant、Rita Scarpelli、Marco Migliore、Clara Albani、Sine Mandrup Bertozzi、Mauro Dionisi、Glauco Tarozzo、Daniele Piomelli、Andrea Cavalli、Marco De Vivo

  DOI：10.1021/jm3011146

  日期：2012.10.25

  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.