1-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-4-(3-furan-3-yl-acryloyl)-piperazine | 70842-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-4-(3-furan-3-yl-acryloyl)-piperazine
• 英文别名: 2-{4-[3-(Furan-3-yl)-acryloyl]-piperazin-1-yl}-4-amino-6,7-dimethoxyquinazoline；1-[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-3-(furan-3-yl)prop-2-en-1-one
• CAS: 70842-93-2
• 化学式: C₂₁H₂₃N₅O₄
• 分子量: 409.445
• InChiKey: NNMCIWBYFKCLHG-UHFFFAOYSA-N

物化性质

• 熔点：
  252-253 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  696.8±65.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  特拉唑嗪杂质D 在 盐酸 、 三乙胺 作用下， 反应 1.5h， 生成 1-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-4-(3-furan-3-yl-acryloyl)-piperazine
  参考文献：
  名称：

  Pyrimidine derivatives. 4. Synthesis and antihypertensive activity of 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline derivatives

  摘要：

  A series of 30 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline derivatives was prepared and tested for their ability to reduce blood pressure in conscious, spontaneously hypertensive rates (SHR). A number of these compounds, notably 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazolines 3a (R1 = H; R2 = Ph), 3j (R1 = H; R2 = 4-EtOPh), and 5a (R1 = H; R2 = 2-furyl), showed activity at oral doses of 0.3-10 mg/kg. The effects of the 4-substituents of the piperazino group on activity are discussed. Compounds 3a, 3j, and 5a were effective in renal hypertensive rats at oral doses of 3 and 10 mg/kg and showed alpha-adrenoceptor blocking effects in isolated aortas of rats. A 5-day consecutive oral administration of 3a and 3j in SHR did not lead to development of tolerance.

  DOI：

  10.1021/jm00357a016

文献信息

• Antihypertensive quinazoline derivatives
  申请人：Mitsubishi Yuka Pharmaceutical Co., Ltd.

  公开号：US04189484A1

  公开（公告）日：1980-02-19

  Novel quinazoline compounds and antihypertensive compositions containing said compounds are disclosed; said compounds having the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group having 1-5 carbon atoms; R.sup.2 is a group of the formula ##STR2## in which Y is a hydrogen atom, an alkyl group of 1-5 carbon atoms, an alkoxy group of 1-5 carbon atoms, an alkenyloxy group, a methylenedioxy group, a nitro group, a halogen atom, a trifluoromethyl group, an acyloxy group, a hydroxy group, an unsubstituted or substituted amino group or a condensed benzene nucleus and m is an integer of 1-3 inclusive, or a group of the formula ##STR3## in which X is an oxygen atom, a sulfur atom or a carbon-nitrogen double bond and Z is a hydrogen atom, an alkyl group of 1-5 carbon atoms, an alkoxy group of 1-5 carbon atoms, a nitro group or a halogen atom; and n is an integer of 2-3 inclusive; provided that, when R.sup.2 is the said group ##STR4## n is 2 and R.sup.1 is a hydrogen atom or, when R.sup.2 is the said group ##STR5## n is 2 or 3 and R.sup.1 is a hydrogen atom or the said alkyl group and a pharmaceutically acceptable acid addition salt thereof.

  本发明揭示了新型喹唑啉化合物和含有该化合物的降压组合物；该化合物的化学式为：##STR1## 其中R.sup.1是氢原子或具有1-5个碳原子的烷基基团；R.sup.2是式##STR2## 的基团，其中Y是氢原子、1-5个碳原子的烷基基团、1-5个碳原子的烷氧基团、烯丙氧基团、亚甲基二氧基基团、硝基基团、卤素原子、三氟甲基基团、酰氧基团、羟基、未取代或取代的氨基基团或缩合苯环，m是1-3的整数，或者是式##STR3## 的基团，其中X是氧原子、硫原子或碳氮双键，Z是氢原子、1-5个碳原子的烷基基团、1-5个碳原子的烷氧基团、硝基或卤素原子；n是2-3的整数；但是，当R.sup.2是所述的基团##STR4## 时，n为2且R.sup.1是氢原子，或者当R.sup.2是所述的基团##STR5## 时，n为2或3且R.sup.1是氢原子或所述的烷基基团，以及其药学上可接受的酸盐。
• Pyrimidine derivatives. 4. Synthesis and antihypertensive activity of 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline derivatives
  作者：Tetsuo Sekiya、Hidetoshi Hiranuma、Shunsuke Hata、Susumu Mizogami、Mitsuo Hanazuka、Shunichi Yamada

  DOI：10.1021/jm00357a016

  日期：1983.3

  A series of 30 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline derivatives was prepared and tested for their ability to reduce blood pressure in conscious, spontaneously hypertensive rates (SHR). A number of these compounds, notably 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazolines 3a (R1 = H; R2 = Ph), 3j (R1 = H; R2 = 4-EtOPh), and 5a (R1 = H; R2 = 2-furyl), showed activity at oral doses of 0.3-10 mg/kg. The effects of the 4-substituents of the piperazino group on activity are discussed. Compounds 3a, 3j, and 5a were effective in renal hypertensive rats at oral doses of 3 and 10 mg/kg and showed alpha-adrenoceptor blocking effects in isolated aortas of rats. A 5-day consecutive oral administration of 3a and 3j in SHR did not lead to development of tolerance.