8-fluoroisoquinoline-5-carboxaldehyde | 679434-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 8-fluoroisoquinoline-5-carboxaldehyde
• 英文别名: 8-Fluoroisoquinoline-5-carbaldehyde
• CAS: 679434-47-0
• 化学式: C₁₀H₆FNO
• 分子量: 175.162
• InChiKey: DKUHIFJOIMCZNU-UHFFFAOYSA-N

物化性质

• 沸点：
  340.3±22.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-fluoroisoquinoline-5-carboxaldehyde 在 三乙基硅烷 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 5-[(5-bromo-1,3-benzodioxol-4-yl)methyl]-8-fluorosoquinoline
  参考文献：
  名称：

  Synthesis and SAR exploration of dinapsoline analogues

  摘要：

  Dinapsoline is a full D-1 dopamine receptor agonist that produces robust otational activity in the unilateral 6-OHDA rat model. This compound is orally active, and shows a low tendency to cause tolerance in rat models. The active enantiomer was determined to have the S-(+) configuration, and the opposite enantiomer is essentially devoid of biological activity. Taken together, dinapsoline has significant metabolic and pharmacological advantages over previous D-1 agonists. In an attempt to define the structure-activity relationships (SARs) and to map out the key elements surrounding the unique structure of dinapsoline, core analogues and substitution analogues of the parent tetracyclic condensed ring structure were prepared. Based on a recently developed synthesis of dinapsoline and its enantiomers, both core and substitution analogues on all four rings (A, B, C and D ring) of dinapsoline were synthesized. It was found that affinity for both D-1 and D-2 receptors was decreased by most substituents on the A, B', and C rings, whereas D ring substitutions preserved much of the dopamine receptor binding activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.015
• 作为产物：
  描述：

  5-溴-8-硝基异喹啉 在 tetrafluoroboric acid 、 正丁基锂 、 铁粉 、 氯化铵 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 8-fluoroisoquinoline-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis and SAR exploration of dinapsoline analogues

  摘要：

  Dinapsoline is a full D-1 dopamine receptor agonist that produces robust otational activity in the unilateral 6-OHDA rat model. This compound is orally active, and shows a low tendency to cause tolerance in rat models. The active enantiomer was determined to have the S-(+) configuration, and the opposite enantiomer is essentially devoid of biological activity. Taken together, dinapsoline has significant metabolic and pharmacological advantages over previous D-1 agonists. In an attempt to define the structure-activity relationships (SARs) and to map out the key elements surrounding the unique structure of dinapsoline, core analogues and substitution analogues of the parent tetracyclic condensed ring structure were prepared. Based on a recently developed synthesis of dinapsoline and its enantiomers, both core and substitution analogues on all four rings (A, B, C and D ring) of dinapsoline were synthesized. It was found that affinity for both D-1 and D-2 receptors was decreased by most substituents on the A, B', and C rings, whereas D ring substitutions preserved much of the dopamine receptor binding activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.015

文献信息

• Amine Compounds
  申请人：Ohmori Yutaka

  公开号：US20080200535A1

  公开（公告）日：2008-08-21

  There is provided a compound exhibiting an activity of suppressing immune response with reduced adverse drug reactions, which compound is useful in the chemotherapy for preventing or treating, for example, a wide range of various autoimmune diseases including systemic erythematodes, chronic rheumatoid arthritis, Type I diabetes, inflammatory bowel disease, biliary cirrhosis, uveitis, multiple sclerosis or other disorders, or chronic inflammatory diseases, or cancers, lymphoma or leukemia, or resistance to organ or tissue transplantation or rejection against transplantation. Novel amine compounds having an S1P1/Edg1 receptor agonist effect, possible stereoisomers or racemic bodies of the compounds, or pharmacologically acceptable salts, hydrates or solvates of the compound, the stereoisomers or the racemic bodies, or prodrugs of the compounds, the stereoisomers, the racemic bodies, the salts, the hydrates or the solvates, are provided.

  提供了一种化合物，具有抑制免疫反应并减少不良药物反应的活性，该化合物在化疗中用于预防或治疗各种自身免疫性疾病，包括系统性红斑狼疮、慢性类风湿关节炎、I型糖尿病、炎症性肠病、胆汁性肝硬化、葡萄膜炎、多发性硬化或其他疾病，慢性炎症性疾病，癌症，淋巴瘤或白血病，器官或组织移植的抗性或对移植的排斥。提供了具有S1P1/Edg1受体激动剂作用的新型胺类化合物，可能是这些化合物的立体异构体或消旋体，或这些化合物、立体异构体或消旋体的药理学上可接受的盐、水合物或溶剂合物，或这些化合物、立体异构体、消旋体、盐、水合物或溶剂的前药。
• Synthesis and SAR exploration of dinapsoline analogues
  作者：S Sit

  DOI：10.1016/j.bmc.2003.11.015

  日期：2004.2.15

  Dinapsoline is a full D-1 dopamine receptor agonist that produces robust otational activity in the unilateral 6-OHDA rat model. This compound is orally active, and shows a low tendency to cause tolerance in rat models. The active enantiomer was determined to have the S-(+) configuration, and the opposite enantiomer is essentially devoid of biological activity. Taken together, dinapsoline has significant metabolic and pharmacological advantages over previous D-1 agonists. In an attempt to define the structure-activity relationships (SARs) and to map out the key elements surrounding the unique structure of dinapsoline, core analogues and substitution analogues of the parent tetracyclic condensed ring structure were prepared. Based on a recently developed synthesis of dinapsoline and its enantiomers, both core and substitution analogues on all four rings (A, B, C and D ring) of dinapsoline were synthesized. It was found that affinity for both D-1 and D-2 receptors was decreased by most substituents on the A, B', and C rings, whereas D ring substitutions preserved much of the dopamine receptor binding activity. (C) 2003 Elsevier Ltd. All rights reserved.