1-Chloro-3-(2-pyridyl)isoquinoline | 58839-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-Chloro-3-(2-pyridyl)isoquinoline
• 英文别名: 1-chloro-3-pyridin-2-yl-isoquinoline；1-chloro-3-pyridin-2-ylisoquinoline
• CAS: 58839-98-8
• 化学式: C₁₄H₉ClN₂
• 分子量: 240.692
• InChiKey: GHWUQXJMRBYBND-UHFFFAOYSA-N

物化性质

• 沸点：
  405.5±35.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Chloro-3-(2-pyridyl)isoquinoline 在 potassium permanganate 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 1-Methanesulfonyl-3-pyridin-2-yl-isoquinoline
  参考文献：
  名称：

  A Novel Class of Adenosine A₃ Receptor Ligands. 1. 3-(2-Pyridinyl)isoquinoline Derivatives

  摘要：

  A series of 3-(2-pyridinyl)isoquinoline derivatives was synthesized as potential antagonists for the human adenosine A(3) receptor by substitution of the 1-position. The compounds were obtained by various synthetic routes from 1-amino-3-(2-pyridinyl)isoquinoline. The affinity was determined in radioligand binding assays for rat brain A(1) and A(2A) receptors and for the cloned human A(3) receptor. A structure-activity relationship analysis indicated that a phenyl group when coupled by a spacer allowing conjugation on position 1 of the isoquinoline ring increased the adenosine A(3) receptor affinity. In contrast, such a phenyl group directly bound to position 1 of the isoquinoline ring decreased affinity. Since the combination of a phenyl group together with a spacer raised adenosine A(3) receptor affinity, various spacers were investigated. VUF8501 (N-[3-(2-pyridinyl)isoquinolin-1-yl]benzamidine (15) showed an affinity at the human adenosine A(3) receptor of 740 nM. Substituent effects on the phenyl group were investigated by in vitro evaluation of a series of substituted benzamidines. Electron-donating groups at the para position of the benzamidine ring increased adenosine A(3) receptor affinity. These investigations led to VUF8505 (4-methoxy-N-[3-(2-pyridinyl)isoquinolin-1-yl]benzamidine (22)), which is a moderately potent and selective ligand for the human adenosine A(3) receptor with an affinity of 310 nM in our test system having negligible affinity for rat A(1) and A(2A) receptors.

  DOI：

  10.1021/jm980036q
• 作为产物：
  描述：

  3-(pyridin-2-yl)isoquinolin-1(2H)-one 在 三氯氧磷 作用下， 反应 3.0h， 生成 1-Chloro-3-(2-pyridyl)isoquinoline
  参考文献：
  名称：

  Fused pyridine derivatives

  摘要：

  目前提供了一种由以下公式表示的缩合吡啶化合物（I）： （其中，R2代表环A代表苯环、吡啶环、噻吩环或呋喃环；B代表其药学上可接受的盐或其水合物，是一种具有血清素拮抗作用的临床上有用的药物，特别用于治疗、改善或预防痉挛性麻痹或改善肌张力过高的中枢肌肉松弛剂。

  公开号：

  US06340759B1

文献信息

• Stability of disubstituted copper complexes in the gas phase analyzed by electrospray ionization mass spectrometry
  作者：Ines Starke、Stefan Kammer、Hans-Jürgen Holdt、Erich Kleinpeter

  DOI：10.1002/rcm.4519

  日期：2010.5.15

  A series of nitrogen ligand (L)/copper complexes of the type [Cu(I)L](+), [Cu(II)L(X)](+) and [Cu(I)L(2)](+) (X = Cl(-), BF(4) (-), acac(-), CH(3)COO(-) and SO(3)CF(3) (-)) was studied in the gas phase by electrospray ionization mass spectrometry. The following ligands (L) were employed: 1,12-diazaperylene (dap), 1,1'-bisisoquinoline (bis), 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen), 2,11-disubstituted

  [Cu（I）L]（+），[Cu（II）L（X）]（+）和[Cu（I）L（2）]（）的一系列氮配体（L）/铜配合物+）（X = Cl（-），BF（4）（-），acac（-），CH（3）COO（-）和SO（3）CF（3）（-））已在气相中进行了研究通过电喷雾电离质谱。使用以下配体（L）：1,12-二氮杂萘（dap），1,1'-双异喹啉（bis），2,2'-联吡啶（bpy），1,10-菲咯啉（phen），2,11 -二取代的1,12-二氮杂戊环（dap），3,3'-二取代的1,1'-双异喹啉（双），5,8-二甲氧基取代的二氮杂戊环（meodap），6,6'-二甲氧基取代的二异喹啉（meobis ）和2,9-二甲基-1,10-菲咯啉（dmphen）。碰撞诱导的分解测量用于评估不同铜络合物的相对稳定性。配体空间排列的影响，考察了络合所用的铜盐的取代基类型和抗衡离子的分子量。发现在溶液中[ML（2）]
• Enantioselective Catalyses; 126: Axially Chiral N,N-Ligands with Binaphthyl/Bipyridyl Structure
  作者：H. Brunner、G. Olschewski、B. Nuber

  DOI：10.1055/s-1999-3424

  日期：1999.3

  N,N-Ligands with combined binaphthyl/bipyridyl structure were synthesized by palladium-catalyzed coupling of 1-naphthylboronic acids with 1-halogenoisoquinoline derivates and with 4-bromo-2-(2-pyridyl)naphtho[2,3-d]-1,3-oxazole. Racemic 1-(2-methoxy-1-naphthyl)-3-(2-pyridyl)isoquinoline was resolved via diastereomeric salt formation with (-)-3-bromocamphor-8-sulfonic acid and the absolute configuration was determined by X-ray analysis.

  通过钯催化 1-萘基硼酸与 1-卤代异喹啉衍生物以及 4-溴-2-(2-吡啶基)萘并[2,3-d]-1,3-恶唑的偶联，合成了具有联萘/联吡啶组合结构的 N,N-配体。外消旋 1-(2-甲氧基-1-萘基)-3-(2-吡啶基)异喹啉通过与(-)-3-溴樟脑-8-磺酸形成非对映异构盐而得到解析，并通过 X 射线分析确定了绝对构型。
• Certain 1,3-disubstituted isoquinoline derivatives
  申请人：Eisai Co., Ltd.

  公开号：US20040204421A1

  公开（公告）日：2004-10-14

  Condensed pyridine compounds represented by formula (I): 1 wherein: R 1 and R 3 are, independently, hydrogen, halogen, lower alkyl, or lower alkoxy; R 2 represents an amino substituent; ring A is a benzene ring, pyridine ring, thiophene ring, or furan ring; and B represents a substituent containing a ring structure. Also, pharmaceutically acceptable salt and hydrates thereof. These compounds are clinically useful medicaments having serotonin antagonism, and in particular, for treating, ameliorating, or preventing spastic paralysis. They are also useful as central muscle relaxants for ameliorating myotonia.

  公式（I）表示的浓缩吡啶化合物：1其中：R1和R3独立地表示氢、卤素、较低的烷基或较低的烷氧基；R2表示氨基取代基；环A是苯环、吡啶环、噻吩环或呋喃环；B表示含有环结构的取代基。此外，还包括其药学上可接受的盐和水合物。这些化合物是具有血清素拮抗作用的临床有用药物，特别是用于治疗、改善或预防痉挛性瘫痪。它们还可用作中枢肌肉松弛剂，以改善肌强直。
• Condensed pyridine compound
  申请人：Eisai Co., Ltd

  公开号：US20020013460A1

  公开（公告）日：2002-01-31

  The present provides a condensed pyridine compound (I) represented by the following formula: 1 ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents 2 its pharmaceutically acceptable salt or hydrates thereof, which isa clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.

  目前提供了一种由以下公式表示的缩合吡啶化合物（I）： 1环A代表苯环、吡啶环、噻吩环或呋喃环；和 B代表其药学上可接受的盐或其水合物，是一种临床上有用的药物，具有5-羟色胺拮抗作用，特别是用于治疗、改善或预防痉挛性瘫痪或中枢肌肉松弛剂，以改善肌强直症。
• FUSED PYRIDINE DERIVATIVES
  申请人：Eisai Co., Ltd.

  公开号：EP1020445A1

  公开（公告）日：2000-07-19

  Clinically highly useful drugs having an antagonism to serotonin, in particular, central muscle relaxing drugs for treating, ameliorating or preventing spastic paralysis or ameliorating myotonia and comprising fused pyridine derivatives represented by general formula (I), pharmacologically acceptable salts thereof or hydrates of either (I) or (1), wherein the ring A represents a benzene, pyridine, thiophene or furan ring; and B represents (2).

  具有血清素拮抗作用的临床高效药物，特别是用于治疗、改善或预防痉挛性瘫痪或改善肌张力障碍的中枢性肌肉松弛药物，包括通式（I）代表的融合吡啶衍生物、其药理学上可接受的盐或(I)或(1)的水合物，其中环A代表苯环、吡啶环、噻吩环或呋喃环；B代表(2)。