3-chloro-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one | 60811-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 3-chloro-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one
• 英文别名: 3-chloro-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one；3-chloro-6,7,8,9-tetrahydro-pyrido[2,1-b]quinazolin-11-one；11H-Pyrido[2,1-b]quinazolin-11-one, 3-chloro-6,7,8,9-tetrahydro-
• CAS: 60811-46-3
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: NEXKQCAKGSVZLK-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  402.9±47.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one 在 sodiumsulfide nonahydrate 、 sodium acetate 、 溶剂黄146 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 (E)-N-(4-((3-chloro-11-oxo-7,8,9,11-tetrahydro-6H-pyrido[2,1-b]quinazolin-6-ylidene)methyl)phenyl)-3-(diethylamino)propanamide
  参考文献：
  名称：

  设计，合成和评估Isaindigotone衍生物作为乙酰胆碱酯酶和淀粉样β聚集的双重抑制剂

  摘要：

  设计，合成和评估了一系列isaindigotone衍生物和类似物，作为胆碱酯酶（ChEs）和自诱导的β-淀粉样蛋白（Aβ）聚集的双重抑制剂。合成的化合物对胆碱酯酶的抑制作用在微摩尔或纳摩尔范围内具有IC 50值，并且某些化合物对AChE的抑制作用强，对AChE的选择性比BuChE高，这要好于我们小组先前报道的异靛酮衍生物。这些化合物中的大多数显示出比参考化合物姜黄素更高的自我诱导的Aβ聚集抑制活性。结构-活性关系研究表明，对AChE具有较高抑制活性的衍生物也显示出对AChE的选择性高于BuChE。化合物6c 使用CD，EM，分子对接和动力学进一步研究了对AChE和自诱导的Aβ聚集均表现出优异抑制作用的分子。

  DOI：

  10.1016/j.bmc.2012.02.061
• 作为产物：
  描述：

  2-羧基-5-氯苯基叠氮化物 在 三甲基氯硅烷 、 氯化亚砜 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 7.25h， 生成 3-chloro-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Pyrrolo[2,1-b]quinazolinones:  Lipase-Catalyzed Resolution of Vasicinone

  摘要：

  A facile synthesis of bronchodilatory pyrrolo [2,1-b] quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.

  DOI：

  10.1021/jo0011484

文献信息

• Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones
  作者：Ahmed Kamal、K.Venkata Ramana、Hari Babu Ankati、A.Venkata Ramana

  DOI：10.1016/s0040-4039(02)01454-5

  日期：2002.9

  FeCl3/NaI has been employed for an efficient reduction of a variety of azides. This method is selective in the presence of a nitro functionality and has been extended for the synthesis of fused [2,1-b]quinazolinone ring systems such as deoxyvasicinone.

  FeCl 3 / NaI已用于有效还原各种叠氮化物。该方法在硝基官能团存在的情况下是选择性的，并且已经扩展为合成稠合的[ 2,1- b ]喹唑啉酮环系统，例如脱氧维辛酮。
• One-Pot Synthesis of Simple Alkaloids: 2,3-Polymethylene-4(3<i>H</i>)-quinazolinones, Luotonin A, Tryptanthrin, and Rutaecarpine
  作者：Katherine Chae Jahng、Seung Ill Kim、Dong Hyeon Kim、Chang Seob Seo、Jong-Keun Son、Seung Ho Lee、Eung Seok Lee、Yurngdong Jahng

  DOI：10.1248/cpb.56.607

  日期：——

  One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl2 is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

  本文描述了从邻氨基苯甲酸、相应的内酰胺和SOCl2中一锅合成多种2,3-聚甲基-4(3H)-喹唑啉酮的方法，该方法可用于合成简单的4(3H)-喹唑啉酮衍生物生物碱，如鲁托霉素A、曲普坦和鲁托卡品。
• Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1)
  作者：Zhuo Chen、Gaoyun Hu、Dai Li、Jun Chen、Yuanjian Li、Huayong Zhou、Ye Xie

  DOI：10.1016/j.bmc.2009.02.015

  日期：2009.3

  Rutaecarpine is the major alkaloid component of Wu-Chu-Yu, a well known Chinese herbal drug. It has been reported that rutaecarpine causes the vasodilator, hypotensive effects by stimulation of CGRP synthesis and release via activation of TRPV1. In present study, 23 rutaecarpine analogues were designed and synthesized. Then, the vasodilator effects of theses compounds were screened by rat aortic ring experiment. The result showed that the 14-N atom of rutaecarpine might be the key site for the activity. The 5-carbonyl might make lower contribution to the effect. And simple substitute in indole-ring or quinazo-line-ring would not enhance the vasodilator effect unless in proper position with proper group. One of these compounds, 10-methylrutaecarpine, exhibited similar effect with rutaecarpine. Further functional experiments showed its vasodilator and hypotensive effect were related to the stimulation of CGRP release via activation of TRPV1. The vasodilator effects of these compounds were evaluated and the structure-activity relationship was elucidated for the first time. The results suggested a new direction of valuable TRPV1 agonist as anti-hypertensive drugs. (C) 2009 Elsevier Ltd. All rights reserved.