(E)-[2-(4-chlorophenyl)-1,2-dihydro-1-oxo-3H-pyrrolo[3,4-b]quinolin-3-ylidene]acetic acid | 180161-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (E)-[2-(4-chlorophenyl)-1,2-dihydro-1-oxo-3H-pyrrolo[3,4-b]quinolin-3-ylidene]acetic acid
• 英文别名: (2E)-2-[2-(4-chlorophenyl)-1-oxopyrrolo[3,4-b]quinolin-3-ylidene]acetic acid
• CAS: 180161-76-6
• 化学式: C₁₉H₁₁ClN₂O₃
• 分子量: 350.761
• InChiKey: FLDGACIWKAVGFE-MHWRWJLKSA-N

物化性质

• 沸点：
  607.8±55.0 °C(Predicted)
• 密度：
  1.584±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-[2-(4-chlorophenyl)-1,2-dihydro-1-oxo-3H-pyrrolo[3,4-b]quinolin-3-ylidene]acetic acid 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (E)-N-benzyl-2-(2-(4-chlorophenyl)-1-oxo-1,2-dihydropyrrolo[3,4-b]quinolin-3-ylidene)-N-methylacetamide
  参考文献：
  名称：

  Molecular Basis of Peripheral vs Central Benzodiazepine Receptor Selectivity in a New Class of Peripheral Benzodiazepine Receptor Ligands Related to Alpidem

  摘要：

  Alpidem (1), the anxiolytic imidazopyridine, has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PER). A novel class of PER ligands related to alpidem has been designed by comparing the interaction models of alpidem with PER and CBR. Several compounds in this class have shown high selectivity for PER vs CBR, and the selectivity has been discussed in terms of interaction models. The binding behavior of the three selected compounds was extensively studied by competition and saturation assays, and the results suggest that they are capable of recognizing two sites labeled by [H-3]PK11195. The molecular structure of one of the most active compounds (4e) has been determined by X-ray diffraction and compared with that of alpidem. Molecular modeling studies suggest that the bioactive conformation of 4e is Likely to be very similar to the conformation found in the crystal.

  DOI：

  10.1021/jm960325j
• 作为产物：
  描述：

  ethyl (E)-3-anilino-4-chlorobut-2-enoate 在 乙酸酐 、 三氯氧磷 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 60.25h， 生成 (E)-[2-(4-chlorophenyl)-1,2-dihydro-1-oxo-3H-pyrrolo[3,4-b]quinolin-3-ylidene]acetic acid
  参考文献：
  名称：

  Molecular Basis of Peripheral vs Central Benzodiazepine Receptor Selectivity in a New Class of Peripheral Benzodiazepine Receptor Ligands Related to Alpidem

  摘要：

  Alpidem (1), the anxiolytic imidazopyridine, has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PER). A novel class of PER ligands related to alpidem has been designed by comparing the interaction models of alpidem with PER and CBR. Several compounds in this class have shown high selectivity for PER vs CBR, and the selectivity has been discussed in terms of interaction models. The binding behavior of the three selected compounds was extensively studied by competition and saturation assays, and the results suggest that they are capable of recognizing two sites labeled by [H-3]PK11195. The molecular structure of one of the most active compounds (4e) has been determined by X-ray diffraction and compared with that of alpidem. Molecular modeling studies suggest that the bioactive conformation of 4e is Likely to be very similar to the conformation found in the crystal.

  DOI：

  10.1021/jm960325j

文献信息

• Synthesis and structure–activity relationship studies in peripheral benzodiazepine receptor ligands related to alpidem
  作者：Andrea Cappelli、Germano Giuliani、Salvatore Valenti、Maurizio Anzini、Salvatore Vomero、Gianluca Giorgi、Cristiana Sogliano、Elisabetta Maciocco、Giovanni Biggio、Alessandra Concas

  DOI：10.1016/j.bmc.2007.06.044

  日期：2008.3.15

  PBR ligands. The target amide derivatives were prepared following a previously published procedure based on the condensation of pyrrolo[3,4-b]quinoline derivatives 11a,b with glyoxylic acid mono-hydrate and the subsequent amidation of the acids obtained via mixed anhydride. On the other hand, the preparation of compound 9g lacking the pharmacophoric (delta1) carbonyl group involved: (a) the double

  为了评估不同类别（和亚类）PBR配体之间的结构亲和性关系的一致性，已进行了与一类新的与杀虫剂相关的外围苯二氮杂receptor受体（PBR）配体的结构亲和性关系的探索。按照吡咯并[3，4-b]喹啉衍生物11a，b与乙醛酸一水合物的缩合反应，随后酰胺化通过混合酸酐得到的酸，按照先前公开的方法制备目标酰胺衍生物。另一方面，缺少药效团（delta1）羰基的化合物9g的制备涉及：（a）从双（二甲基氨基）甲烷和乙酰氯获得的二甲基亚甲基铵盐对吡咯并[3,4-b]的两次连续进攻喹啉衍生物11b （b）用甲基碘将获得的烯丙胺衍生物13季铵化，以及（c）N-甲基-对茴香胺被季铵盐阳离子14钯催化的烯丙基化。在该三环亚类中观察到结构亲和性趋势利培芬相关的PBR配体在PBR配体的其他类别（或亚类）中发现相关性。该结果支持最初的药效学假说，并提出了在PBR结合位点的共同相互作用方式。
• Molecular Basis of Peripheral vs Central Benzodiazepine Receptor Selectivity in a New Class of Peripheral Benzodiazepine Receptor Ligands Related to Alpidem
  作者：Maurizio Anzini、Andrea Cappelli、Salvatore Vomero、Gianluca Giorgi、Thierry Langer、Giancarlo Bruni、Maria R. Romeo、Anthony S. Basile

  DOI：10.1021/jm960325j

  日期：1996.1.1

  Alpidem (1), the anxiolytic imidazopyridine, has nanomolar binding affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PER). A novel class of PER ligands related to alpidem has been designed by comparing the interaction models of alpidem with PER and CBR. Several compounds in this class have shown high selectivity for PER vs CBR, and the selectivity has been discussed in terms of interaction models. The binding behavior of the three selected compounds was extensively studied by competition and saturation assays, and the results suggest that they are capable of recognizing two sites labeled by [H-3]PK11195. The molecular structure of one of the most active compounds (4e) has been determined by X-ray diffraction and compared with that of alpidem. Molecular modeling studies suggest that the bioactive conformation of 4e is Likely to be very similar to the conformation found in the crystal.