2-chloro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one | 60811-47-4

• 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: 2-chloro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one
• 英文别名: 2-chloro-6,7,8,9-tetrahydro-pyrido[2,1-b]quinazolin-11-one；2-chloro-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one
• CAS: 60811-47-4
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: MYRYPTDWOINKAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °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：

  2-chloro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one 在 乙酸酐 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 2-chloro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazoline-6,11-dione
  参考文献：
  名称：

  新型拓扑异构酶抑制剂：芸香碱衍生物的合成及其对拓扑异构酶的抑制活性

  摘要：

  采用先前报道的方法制备了一系列芸香碱衍生物，并评估了它们对拓扑异构酶 I 和 II 的抑制活性。其中，强细胞毒性的 10-bromorutaecarpine 和 3-chlororutaecarpine 对拓扑 I 和 II 显示出强烈的抑制活性。

  DOI：

  10.1007/s12272-012-0504-1
• 作为产物：
  描述：

  2-Azido-5-chlorobenzoyl chloride 在 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-chloro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one
  参考文献：
  名称：

  One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

  摘要：

  Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.09.046

文献信息

• A Polymer-Assisted Solution-Phase Strategy for the Synthesis of Fused [2,1-<i>b</i>]Quinazolinones and the Preparation of Optically Active Vasicinone
  作者：Ahmed Kamal、V. Devaiah、N. Shankaraiah、K. Reddy

  DOI：10.1055/s-2006-951482

  日期：2006.9

  An efficient preparation of fused [2,1-b]quinazolinones has been developed utilizing polymer-supported reagents. (±)-Vasicinone was converted into its dione by oxidation with poly (4-vinylpyridiniumdichromate). An efficient method has been developed for the synthesis of (d)- and (l)-vasicinone via asymmetric reduction of pyrrolo[2,l-b]quinazoline-3,9-dione by employing NaBH 4 /Me 3 SiCl as the reducing

  利用聚合物支持的试剂开发了一种有效制备稠合 [2,1-b] 喹唑啉酮的方法。(±)-Vasicinone 通过用聚（4-乙烯基吡啶重铬酸盐）氧化转化为二酮。已经开发了一种通过使用 NaBH 4 /Me 3 SiCl 作为还原剂和 pyrrolo[2,lb]quinazoline-3,9-dione 的不对称还原来合成 (d)- 和 (l)-vasicinone 的有效方法。聚合物负载的手性磺酰胺作为催化剂。
• Novel One-Pot Total Syntheses of Deoxyvasicinone, Mackinazolinone, Isaindigotone, and Their Derivatives Promoted by Microwave Irradiation
  作者：Ji-Feng Liu、Ping Ye、Kevin Sprague、Katie Sargent、Daniel Yohannes、Carmen M. Baldino、Christopher J. Wilson、Shi-Chung Ng

  DOI：10.1021/ol0513084

  日期：2005.7.1

  [reaction: see text]. Total syntheses of deoxyvasicinone (1), mackinazolinone (2), and 8-hydroxydeoxyvasicinone (3) via novel microwave-assisted domino reactions, as well as a novel three-component one-pot total synthesis of isaindigotone (5) promoted by microwave irradiation, are reported. The efficient reaction process enabled us to rapidly access related natural product derivatives and to identify

  [反应：请参见文字]。通过新型的微波辅助多米诺反应合成脱氧维西酮（1），麦金唑啉酮（2）和8-羟基脱氧维西酮（3）以及通过微波辐射促进的新的三组分一锅异靛酮的全合成（5） ，均已报告。高效的反应过程使我们能够快速获取相关的天然产物衍生物，并鉴定出一类新的细胞毒剂。
• One-Pot Synthesis of Simple Alkaloids: 2,3-Polymethylene-4(3&lt;i&gt;H&lt;/i&gt;)-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.
• Koekoesi, Jozsef; Hermecz, Istvan; Podanyi, Benjamin, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1301 - 1306
  作者：Koekoesi, Jozsef、Hermecz, Istvan、Podanyi, Benjamin、Szasz, Gyoergy、Meszaros, Zoltan

  DOI：——

  日期：——