3,4-dihydro-2H-benzo[h]isoquinolin-1-one | 73130-32-2

• 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: 3,4-dihydro-2H-benzo[h]isoquinolin-1-one
• 英文别名: 3,4-dihydrobenz[h]isoquinolin-1(2H)-one；3,4-dihydro-2H-benzo[h]isoquinolin-1-one；3,4-Dihydrobenzisochinolin-1(2H)-on
• CAS: 73130-32-2
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: ZEESLHGIDIWIEM-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  486.5±25.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2H-benzo[h]isoquinolin-1-one 在 硫酸 、 potassium nitrate 作用下， 反应 1.0h， 以12%的产率得到7-nitro-3,4-dihydrobenz[h]isoquinolin-1(2H)-one
  参考文献：
  名称：

  Exploring the active site of phenylethanolamine N-methyltransferase with 1,2,3,4-tetrahydrobenz[h]isoquinoline inhibitors☆

  摘要：

  1,2,3,4-Tetrahydrobenz[h]isoquinoline (THBQ, 11) is a potent, inhibitor of phenylethanolamine N-methyltransferase (PNMT). Docking studies indicated that the enhanced PNMT inhibitory potency of 11 (hPNMT K-i = 0.49 mu M) versus 1,2,3,4-tetrahydroisoquinoline (5, hPNMT Ki = 5.8 mu M) was likely due to hydrophobic interactions with Val53, Met258, Val272, and Val269 in the PNMT active site. These studies also suggested that the addition of substituents to the 7-position of 11 that are capable of forming hydrogen bonds to the enzyme could lead to compounds (14-18) having enhanced PNMT inhibitory potency. However, these compounds are in fact less potent at PNMT than 11. Furthermore, 7-bromo-THBQ (19, hPNMT Ki = 0.22 mM), which has a lipophilic 7-substituent that cannot hydrogen bond to the enzyme, is twice as potent at PNMT than 11. This once again illustrates the limitations of docking studies for lead optimization. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.010
• 作为产物：
  描述：

  (2-naphthalen-2-yl-ethyl)-carbamic acid ethyl ester 在 phosphorus pentoxide 、 三氯氧磷 作用下， 反应 3.0h， 以40%的产率得到3,4-dihydro-2H-benzo[h]isoquinolin-1-one
  参考文献：
  名称：

  17a-HYDROXYLASE/C17,20-LYASE INHIBITORS

  摘要：

  本发明提供了式（I）的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、A和n如本文所定义。还提供了式（I）化合物的氘代衍生物。

  公开号：

  US20140045872A1

文献信息

• [EN] 17a-HYDROXYLASE/C17,20-LYASE INHIBITORS<br/>[FR] INHIBITEURS DE LA 17?-HYDROXYLASE/C17,20-LYASE
  申请人：NOVARTIS AG

  公开号：WO2012035078A1

  公开（公告）日：2012-03-22

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

  本发明提供了式（I）的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、A和n如本文所定义。还提供了式（I）化合物的氘代衍生物。
• Imidazole derivatives
  申请人：Glaxo Group Limited

  公开号：US05116984A1

  公开（公告）日：1992-05-26

  The invention relates to imidazole derivatives of the general formula (I) ##STR1## wherein Im represents an imidazolyl group of formula: ##STR2## A represents the group CH or a nitrogen atom; R.sup.1 and R.sup.2, which may be the same or different, and may be attached to either the same or different fused rings of the naphthalene moiety, each represents a hydrogen atom, a halogen atom, or a hydroxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl or C.sub.1-4 alkylthio group, and one of R.sup.1 and R.sup.2 may also represent a group --NR.sup.3 R.sup.4 (wherein R.sup.3 and R.sup.4, which may be the same or different, each represents a hydrogen atom or a C.sub.1-4 alkyl group, or together with the nitrogen atom to which they are attached form a saturated 5 to 7 membered ring); n represents 1, 2 or 3; R.sup.5, R.sup.6, R.sup.7, are as defined in the specification; and physiologically acceptable salts and solvates thereof.

  本发明涉及一般式(I)的咪唑衍生物：##STR1## 其中Im代表式为：##STR2## 的咪唑基团；A代表CH基团或氮原子；R1和R2，可以相同也可以不同，可以连接在萘基团的同一环或不同环上，每个R1和R2代表氢原子、卤素原子、羟基、C.sub.1-4烷氧基、C.sub.1-4烷基或C.sub.1-4烷硫基团，其中R1和R2中的一个还可以代表--NR.sup.3R.sup.4基团（其中R.sup.3和R.sup.4可以相同也可以不同，每个代表氢原子或C.sub.1-4烷基，或者与它们所连接的氮原子形成饱和的5到7元环）；n代表1、2或3；R5、R6、R7如说明书中所定义；以及其生理上可接受的盐和溶剂化合物。
• 17α-hydroxylase/C17,20-lyase inhibitors
  申请人：Bock Mark Gary

  公开号：US08946260B2

  公开（公告）日：2015-02-03

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

  本发明提供了化合物(I)的衍生物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、A和n的定义如本文所述。还提供了化合物(I)的氘代衍生物。
• Facile Synthesis of 5- to 7-Membered Benzolactam Compounds via Strongly Facilitated Electrophilic Aromtic Substitution Reaction†
  作者：Tomohiko Ohwada、Hiroaki Kurouchi、Yuko Otani

  DOI：10.3987/com-15-s(t)60

  日期：——

  We employed our system to activate aromatic ring-tethered carbamate compounds with trifluoromethanesulfonic acid to obtain benzolactams with 5- to 7-membered rings, and examined the substrate scope and limitations of this activation method. In 5-membered ring formation, a halogen group on the aromatic ring did not greatly affect the reaction yield, but other electron-donating groups inhibited the cyclization reaction, and various side-reactions occurred. In 7-membered ring formation, eletron-donating groups on aromatic ring promoted the cyclization reaction, but cyclization of electron-deficient aromatic rings did not proceed well. The 6-membered ring formation reaction showed the greatest substrate generality.
• BEAUMONT D.; WAIGH R. D., J. CHEM. RES. SYNOP., 1979, NO 10, 332, (M 3864-3877)
  作者：BEAUMONT D.、 WAIGH R. D.

  DOI：——

  日期：——