2-(4-(naphthalen-1-ylamido)phenyl)acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-(naphthalen-1-ylamido)phenyl)acetic acid
• 英文别名: [4-(1-Naphthoylamino)phenyl]acetic acid；2-[4-(naphthalene-1-carbonylamino)phenyl]acetic acid
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: RUFBMSTUAPVRGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氧化碳-13C 、 2-(4-(naphthalen-1-ylamido)phenyl)acetic acid 在 potassium phosphate 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以72%的产率得到
  参考文献：
  名称：

  CO 2与碳同位素交换的光化学策略

  摘要：

  报道了用于碳同位素交换的光催化方法。利用[ 13 C] CO 2和[ 14 C] CO 2作为主要的C1来源，该方案可将所需的碳同位素插入苯基乙酸中，而无需在单个步骤中进行结构修饰或预功能化。这种无痕转化所需要的异常温和的条件与先前要求使用苛刻的热条件的方法形成了鲜明的对比。

  DOI：

  10.1021/acscatal.0c05344
• 作为产物：
  描述：

  对氨基苯乙酸 、 1-萘甲酰氯 在 吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以55%的产率得到2-(4-(naphthalen-1-ylamido)phenyl)acetic acid
  参考文献：
  名称：

  Structural optimization and in vitro profiling of N-phenylbenzamide-based farnesoid X receptor antagonists

  摘要：

  Activation of the nuclear farnesoid X receptor (FXR) which acts as cellular bile acid sensor has been validated as therapeutic strategy to counter liver disorders such as non-alcoholic steatohepatitis by the clinical efficacy of obeticholic acid. FXR antagonism, in contrast, is less well studied and potent small molecule FXR antagonists are rare. Here we report the systematic optimization of a novel class of FXR antagonists towards low nanomolar potency. The most optimized compound antagonizes baseline and agonist induced FXR activity in a full length FXR reporter gene assay and represses intrinsic expression of FXR regulated genes in hepatoma cells. With this activity and a favorable toxicity-, stability- and selectivity-profile it appears suitable to further study FXR antagonism in vitro and in vivo.

  DOI：

  10.1016/j.bmc.2018.07.017

文献信息

• [EN] MODIFIED PENTAPEPTIDE ANTAGONISTS OF THE ATRIAL NATRIURETIC PEPTIDE CLEARANCE RECEPTOR<br/>[FR] ANTAGONISTES DE PENTAPEPTIDES MODIFIES DU RECEPTEUR DE LA CLAIRANCE DES PEPTIDES NATRIURETIQUES AURICULAIRES
  申请人：ASTRAZENECA AB

  公开号：WO2000061631A1

  公开（公告）日：2000-10-19

  A compound having general formula (A) and methods of using such compounds for the treatment of diseases and pharmaceutical composition comprising such compounds.
• Structural optimization and in vitro profiling of N-phenylbenzamide-based farnesoid X receptor antagonists
  作者：Jurema Schmidt、Simone Schierle、Leonie Gellrich、Astrid Kaiser、Daniel Merk

  DOI：10.1016/j.bmc.2018.07.017

  日期：2018.8

  Activation of the nuclear farnesoid X receptor (FXR) which acts as cellular bile acid sensor has been validated as therapeutic strategy to counter liver disorders such as non-alcoholic steatohepatitis by the clinical efficacy of obeticholic acid. FXR antagonism, in contrast, is less well studied and potent small molecule FXR antagonists are rare. Here we report the systematic optimization of a novel class of FXR antagonists towards low nanomolar potency. The most optimized compound antagonizes baseline and agonist induced FXR activity in a full length FXR reporter gene assay and represses intrinsic expression of FXR regulated genes in hepatoma cells. With this activity and a favorable toxicity-, stability- and selectivity-profile it appears suitable to further study FXR antagonism in vitro and in vivo.
• Photochemical Strategy for Carbon Isotope Exchange with CO₂
  作者：Victor Babin、Alex Talbot、Alexandre Labiche、Gianluca Destro、Antonio Del Vecchio、Charles S. Elmore、Frédéric Taran、Antoine Sallustrau、Davide Audisio

  DOI：10.1021/acscatal.0c05344

  日期：2021.3.5

  A photocatalytic approach for carbon isotope exchange is reported. Utilizing [13C]CO2 and [14C]CO2 as primary C1 sources, this protocol allows the insertion of the desired carbon isotope into phenyl acetic acids without the need for structural modifications or prefunctionalization in one single step. The exceptionally mild conditions required for this traceless transformation are in stark contrast

  报道了用于碳同位素交换的光催化方法。利用[ 13 C] CO 2和[ 14 C] CO 2作为主要的C1来源，该方案可将所需的碳同位素插入苯基乙酸中，而无需在单个步骤中进行结构修饰或预功能化。这种无痕转化所需要的异常温和的条件与先前要求使用苛刻的热条件的方法形成了鲜明的对比。