1-benzoyl-1,2,3,4-tetrahydrobenzo-1,5-naphthyridine | 106351-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-benzoyl-1,2,3,4-tetrahydrobenzo-1,5-naphthyridine
• 英文别名: 1-benzoyl-1,2,3,4-tetrahydrobenzo[c]-1,5-naphthyridine；3,4-dihydro-2H-benzo[h][1,5]naphthyridin-1-yl(phenyl)methanone
• CAS: 106351-32-0
• 化学式: C₁₉H₁₆N₂O
• 分子量: 288.349
• InChiKey: IJPVMQXHQCSBGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,3,4-tetrahydrobenzo-1,5-naphthyridine 生成 1-benzoyl-1,2,3,4-tetrahydrobenzo-1,5-naphthyridine
  参考文献：
  名称：

  MARTIN, LAWRENCE L.;SETESCAK, LINDA L.;SCOTT, SUSAN J.

  摘要：

  DOI：

文献信息

• Synthesis of novel 1,2,3,4-tetrahydrobenzo[<i>c</i>]-1,5-naphthyridines from pyrrolo[1,2-<i>b</i>]isoquinolines
  作者：Lawrence L. Martin、Susan J. Scott、Linda L. Setescak、Donna Van Engen

  DOI：10.1002/jhet.5570240609

  日期：1987.11

  (5a) was prepared by a novel synthetic route involving the rearrangement of (±)-(Z)-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dione oxime to afford 1,4-dihydrobenzo[c]-1,5-naphthyridin-2(3H)-one, which was reduced to 5a. The cholinomimetic activity observed with 5a prompted the synthesis and biological evaluation of additional analogues.

  1,2,3,4-四氢苯并[ c ] -1,5-萘啶（5a）是通过涉及（±）-（Z）-1,10a-二氢吡咯并[1,2- b ]异喹啉-3,10（2 H，5 H）-二酮肟制得1,4-二氢苯并[ c ] -1,5-萘啶-2（3 H）-一，还原为5a。用5a观察到的拟胆碱活性促使其他类似物的合成和生物学评估。
• Benzo(c)-1,5-naphthyridines useful for treating a patient having drug
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04652567A1

  公开（公告）日：1987-03-24

  There are disclosed novel compounds of the formula ##STR1## where X is H, halogen, loweralkyl, loweralkoxy, --CF.sub.3, or --OH; R is H, loweralkyl, arylloweralkyl, diarylloweralkyl, loweralkanoyl, arylloweralkanoyl or diarylloweralkanoyl; and R.sub.1 is H.sub.2, O or --NR.sub.2 R.sub.3, R.sub.2 and R.sub.3 being independently H or loweralkyl, or taken together with the nitrogen atom to which they are attached constitute ##STR2## R.sub.4 in turn being H, loweralkyl, hydroxyloweralkyl, aryl, arylloweralkyl or diarylloweralkyl or pharmaceutically acceptable acid addition salts thereof, which are useful for enhancing memory.

  公开了一种新型化合物，其化学式为##STR1##其中X为H、卤素、低碳基、低氧基、--CF.sub.3或--OH；R为H、低碳基、芳基低碳基、二芳基低碳基、低碳酰基、芳基低碳酰基或二芳基低碳酰基；R.sub.1为H.sub.2、O或--NR.sub.2 R.sub.3，其中R.sub.2和R.sub.3独立地为H或低碳基，或与它们连接的氮原子一起构成##STR2##R.sub.4又为H、低碳基、羟基低碳基、芳基、芳基低碳基或二芳基低碳基，或其药学上可接受的酸盐，其用于增强记忆。
• Dihydropyrrolo[1,2-b]isoquinolinedione oximes
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04670562A1

  公开（公告）日：1987-06-02

  There is disclosed novel compounds of the formula ##STR1## where X is H, halogen, loweralkyl, loweralkoxy, -CF.sub.3, or -OH; R is H, loweralkyl, arylloweralkyl, diarylloweralkyl, loweralkanoyl, arylloweralkanoyl or diarylloweralkanoyl; and R.sub.1 is H.sub.2, O or --NR.sub.2 R.sub.3, R.sub.2 and R.sub.3 being independently H or loweralkyl, or taken together with the nitrogen atom to which they are attached constitute ##STR2## R.sub.4 in turn being H, loweralkyl, hydroxyloweralkyl, aryl, arylloweralkyl or diarylloweralkyl or pharmaceutically acceptable acid addition salts thereof, which are useful for enchancing memory.

  公开了新型化合物的公式 ##STR1## 其中X为H、卤素、低烷基、低烷氧基、-CF.sub.3或-OH; R为H、低烷基、芳基低烷基、二芳基低烷基、低烷酰基、芳基低烷酰基或二芳基低烷酰基; R.sub.1为H.sub.2、O或--NR.sub.2 R.sub.3，其中R.sub.2和R.sub.3独立地为H或低烷基，或与它们连接的氮原子一起构成 ##STR2## R.sub.4则为H、低烷基、羟基低烷基、芳基、芳基低烷基或二芳基低烷基或其药学上可接受的酸盐，用于增强记忆。
• Method of synthesizing 1,4-dihydro-benzo[c]-1,5-naphthyridin-2(3H)-ones
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04742171A1

  公开（公告）日：1988-05-03

  There is described a method of synthesizing 1,4-dihydro-benzo[c]-1,5-naphthyridin-2(3H)-ones having the formula ##STR1## where X is hydrogen, halogen, loweralkyl, loweralkoxy, trifluoromethyl or hydroxy, which method consists essentially of the aromatization and rearrangement of 1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dione oximes of the formula below: ##STR2##

  描述了一种合成具有以下公式的1,4-二氢苯并[c]-1,5-萘啉-2(3H)-酮的方法：##STR1## 其中X是氢，卤素，较低烷基，较低烷氧基，三氟甲基或羟基，该方法基本上包括以下化合物的芳香化和重排：1,10a-二氢吡咯并[1,2-b]异喹啉-3,10(2H,5H)-二酮肟的公式如下：##STR2##
• Benzoc[c]-1,5-naphthyridines and related compounds as memory enhancing
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04742061A1

  公开（公告）日：1988-05-03

  There are disclosed novel compounds of the formula ##STR1## where m is 1 or 2; each X is independently H, halogen, loweralkyl, loweralkoxy, --CF.sub.3, or --OH; R is H, loweralkyl, chloroloweralkyl, bromoloweralkyl, iodoloweralkyl, aminoloweralkyl, loweralkylaminoloweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, thienylloweralkyl, furylloweralkyl, loweralkanoyl, chloroloweralkanoyl, bromoloweralkanoyl, iodoloweralkanoyl, aminoloweralkanoyl, loweralkylaminoloweralkanoyl, diloweralkylaminoloweralkanoyl, aroyl, arylloweralkanoyl or diarylloweralkanoyl, thienylloweralkanoyl, furylloweralkanoyl; and R.sub.1 is .dbd.O, ##STR2## or --NR.sub.2 R.sub.3, R.sub.2 and R.sub.3 being independently H or loweralkyl, or taken together with the nitrogen atom to which they are attached constituting ##STR3## R.sub.4 in turn being H, loweralkyl, hydroxyloweralkyl, aryl, arylloweralkyl or diarylloweralkyl, with the proviso that when R.sub.1 is --NR.sub.2 R.sub.3, R is nonexistent, that when R.sub.1 is .dbd.O, R is not an acyl group and that when R.sub.1 is ##STR4## R is not chloroloweralkyl, bromoloweralkyl or iodoloweralkyl; or pharmaceutically acceptable acid addition salts thereof, which are useful for enhancing memory.

  公开了新的化合物，其化学式为## STR1 ##，其中m为1或2;每个X独立地为H，卤素，较低的烷基，较低的烷氧基，-CF.sub.3或-OH;R为H，较低的烷基，氯代较低的烷基，溴代较低的烷基，碘代较低的烷基，氨基较低的烷基，较低的烷基氨基较低的烷基，双较低的烷基氨基较低的烷基，芳基较低的烷基，二芳基较低的烷基，噻吩基较低的烷基，呋喃基较低的烷基，较低的烷酰基，氯代较低的烷酰基，溴代较低的烷酰基，碘代较低的烷酰基，氨基较低的烷酰基，较低的烷基氨基较低的烷酰基，二较低的烷基氨基较低的烷酰基，芳基，芳基较低的烷酰基或二芳基较低的烷酰基，噻吩基较低的烷酰基，呋喃基较低的烷酰基;R.sub.1为.dbd.O，## STR2 ##或-NR.sub.2R.sub.3，其中R.sub.2和R.sub.3独立地为H或较低的烷基，或与它们连接的氮原子一起构成## STR3 ##，R.sub.4反过来为H，较低的烷基，羟基较低的烷基，芳基，芳基较低的烷基或二芳基较低的烷基，但有一个前提，即当R.sub.1为-NR.sub.2R.sub.3时，R不存在，当R.sub.1为.dbd.O时，R不是酰基，当R.sub.1为## STR4 ##时，R不是氯代较低的烷基，溴代较低的烷基或碘代较低的烷基;或其药学上可接受的酸盐，可用于增强记忆。