2-(3-phenyl-2-piperidin-1-yl-4H-quinazolin-4-yl)acetic acid | 200571-81-9

• 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: 2-(3-phenyl-2-piperidin-1-yl-4H-quinazolin-4-yl)acetic acid
• CAS: 200571-81-9
• 化学式: C₂₁H₂₃N₃O₂
• 分子量: 349.433
• InChiKey: BFQWMOFSXCHUDB-UHFFFAOYSA-N

物化性质

• 沸点：
  540.3±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-phenyl-2-piperidin-1-yl-4H-quinazolin-4-yl)acetic acid 在 palladium on activated charcoal 吡啶 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 KYS05042
  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
• 作为产物：
  描述：

  2-nitrocinnamic acid 在 lithium hydroxide 、 硫酸 、 三乙胺 、 tin(ll) chloride 、 二溴三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 20.0h， 生成 2-(3-phenyl-2-piperidin-1-yl-4H-quinazolin-4-yl)acetic acid
  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

文献信息

• Solid-phase synthesis of 3,4-dihydroquinazoline
  作者：Fengjiang Wang、James R. Hauske

  DOI：10.1016/s0040-4039(97)10377-x

  日期：1997.12

  A novel, facile and efficient method for the synthesis of aryl iminophosphorane has been developed by treating a series of Ar-NH2 (1) attached to a solid support with Ph3P and diethyl azodicarboxylate at room temperature. The resulting solid-supported cinnamyl iminophosphorane (4) was treated with an aryl isocyanate to generate the corresponding solid-supported carbodiimide (5), which upon exposure to a secondary amine underwent 1,2-addition followed by an intramolecular Michael addition to afford the desired 3,4-dihydroquinazoline (7). (C) 1997 Elsevier Science Ltd.
• 3,4-Dihydroquinazoline derivatives as T-type calcium channel blockers and method of preparing the same
  申请人：Korea Institute of Science and Technology

  公开号：EP1568695B1

  公开（公告）日：2016-03-09
• 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