4-methoxycarbonylmethyl-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline | 174534-47-5

• 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: 4-methoxycarbonylmethyl-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline
• 英文别名: methyl 2-(3-phenyl-2-piperidin-1-yl-4H-quinazolin-4-yl)acetate
• CAS: 174534-47-5
• 化学式: C₂₂H₂₅N₃O₂
• 分子量: 363.459
• InChiKey: KJQOEXRCADXDKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxycarbonylmethyl-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-carboxy-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline
  参考文献：
  名称：

  3,4-Dihydroquinazoline derivatives as T-type calcium channel blockers and method of preparing the same

  摘要：

  本发明涉及3,4-二氢喹唑啉衍生物作为T型钙通道阻滞剂以及其制备方法。本发明还涉及包含该衍生物的组合物。本发明的3,4-二氢喹唑啉衍生物组合物可有效用于通过阻塞T型钙通道预防和治疗心绞痛、高血压、心肌病、疼痛和癫痫。

  公开号：

  US20050197351A1
• 作为产物：
  描述：

  2-nitrocinnamic acid 在 硫酸 、 三乙胺 、 tin(ll) chloride 、 二溴三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 18.0h， 生成 4-methoxycarbonylmethyl-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline
  参考文献：
  名称：

  Synthesis and SAR studies of a novel series of T-type calcium channel blockers

  摘要：

  For the novel, potent, and selective T-type Ca2+ channel blockers, a series of sulfonamido-containing 3,4-dihydroquinazoline derivatives were prepared and evaluated for their blocking actions on T- and N-type Ca2+ channels. Among them, 9c (KYS05064, IC50 = 0.96 +/- 0.22 mu M) was found to be as potent as Mibefradil and also showed the highest selectivity for T-type Ca2+ channel with no effect on N-type Ca2+ channel. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.01.005
• 作为试剂：
  描述：

  哌啶 、 (E)-3-(2-Phenyliminomethyleneamino-phenyl)-acrylic acid methyl ester 在 水 、 Brine 、 magnesium sulfate 、 4-methoxycarbonylmethyl-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline 、 crystal 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 4-methoxycarbonylmethyl-2-(1-piperidinyl)-3-phenyl-3,4-dihydroquinazoline
  参考文献：
  名称：

  3,4-dihydroquinazoline derivatives as T-type calcium channel blockers and method of preparing the same

  摘要：

  本发明涉及作为T型钙通道阻滞剂的3,4-二氢喹唑啉衍生物及其制备方法。本发明还涉及包含该衍生物的组合物。本发明中包含3,4-二氢喹唑啉衍生物的组合物可以通过阻塞T型钙通道有效地用于预防和治疗心绞痛、高血压、心肌病、疼痛和癫痫。

  公开号：

  US07271260B2

文献信息

• A facile and efficient carbodiimide-mediated synthesis of dihydroquinazolines via a tandem nucleophilic addition-intramolecular hetero conjugate addition annulation strategy
  作者：Takao Saito、Kensaku Tsuda、Yoji Saito

  DOI：10.1016/0040-4039(95)02130-2

  日期：1996.1

  A novel and efficient method is described for the synthesis of dihydroquinazoline derivatives which involves initial addition of a nucleophile (alcohol, amine and thiol) to the carbodiimide cumulenic system followed by intramolecular hetero conjugate addition annulation.

  描述了用于合成二氢喹唑啉衍生物的新颖且有效的方法，该方法包括将亲核试剂（醇，胺和硫醇）初始添加至碳二亚胺累积体系中，然后进行分子内杂共轭物加成环合。
• 3,4-Dihydroquinazoline derivatives as novel selective T-type Ca2+ channel blockers
  作者：Yong Sup Lee、Bum Hoon Lee、Seong Jun Park、Soon Bang Kang、Hyewhon Rhim、Jin-Yong Park、Jung-Ha Lee、Seong-Woo Jeong、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2004.04.090

  日期：2004.7

  For LVA T-type Ca2+ channel blockers, 3,4-dihydroquinazoline derivatives as new scaffolds were prepared and evaluated for the inhibitory activity against two members of the recombinant T-type Ca2+ channel family. Among them, 8a (KYS05001, IC50 = 0-9 muM) was nearly equipotent with mibefradil (IC50 = 0.84 muM) and inhibited LVA T-type Ca2+ channel with greater efficacy than HVA Ca2+ channel. (C) 2004 Elsevier Ltd. All rights reserved.
• T-type Ca2+ channel blockers suppress the growth of human cancer cells
  作者：Jae Ho Heo、Han Na Seo、Yun Jeong Choe、Sujin Kim、Chun Rim Oh、Young Deuk Kim、Hyewhon Rhim、Dong Joon Choo、Jungahn Kim、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2008.06.034

  日期：2008.7

  In order to further clarify the role of T-type Ca2+ channels in cell proliferation, we have measured the growth inhibition of human cancer cells by using our potent T-type Ca2+ channel blockers. As a result, KYS05090, a most potent T-type Ca2+ channel blocker, was found to be as potent as doxorubicin against some human cancer cells without acute toxicity. Therefore, this letter provides the biological results that T-type calcium channel is important in regulating the important cellular phenotype transition leading to cell proliferation, and thus novel T-type Ca2+ channel blocker presents new prospects for cancer treatment. (C) 2008 Elsevier Ltd. All rights reserved.
• US7271260B2
  申请人：——

  公开号：US7271260B2

  公开（公告）日：2007-09-18
• Synthesis and SAR studies of a novel series of T-type calcium channel blockers
  作者：Seong Jun Park、Sung Jun Park、Min Joo Lee、Hyewhon Rhim、Yoonjee Kim、Jung-Ha Lee、Bong Young Chung、Jae Yeol Lee

  DOI：10.1016/j.bmc.2006.01.005

  日期：2006.5

  For the novel, potent, and selective T-type Ca2+ channel blockers, a series of sulfonamido-containing 3,4-dihydroquinazoline derivatives were prepared and evaluated for their blocking actions on T- and N-type Ca2+ channels. Among them, 9c (KYS05064, IC50 = 0.96 +/- 0.22 mu M) was found to be as potent as Mibefradil and also showed the highest selectivity for T-type Ca2+ channel with no effect on N-type Ca2+ channel. (c) 2006 Published by Elsevier Ltd.