7-amino-3-(2-chloroethyl)-2,4(1H,3H)-quinazolinedione | 101389-50-8

• 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: 7-amino-3-(2-chloroethyl)-2,4(1H,3H)-quinazolinedione
• 英文别名: 7-amino-3-(2-chloroethyl)-1,2,3,4-tetrahydroquinazoline-2,4-dione；7-amino-3-(2-chloroethyl)-1H-quinazoline-2,4-dione
• CAS: 101389-50-8
• 化学式: C₁₀H₁₀ClN₃O₂
• 分子量: 239.661
• InChiKey: LFQKLXCSYVAFSN-UHFFFAOYSA-N

物化性质

• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-amino-3-(2-chloroethyl)-2,4(1H,3H)-quinazolinedione 在 palladium on activated charcoal 、 calcium oxide 噻吩 、 超重氢 、 sodium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 7-氨基-3-[2-[4-(4-氟-2-氚苯甲酰基)哌啶-1-基]乙基]-1H-喹唑啉-2,4-二酮
  参考文献：
  名称：

  In vitro labeling of serotonin-S2 receptors. Synthesis and binding characteristics of [3H]-7-aminoketanserin

  摘要：

  [3H]-7-Aminoketanserin (7-amino-3-[2-[4-(2-tritio-4-fluorobenzoyl)-1- piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione), an amino derivative of the selective serotonin-S2 antagonist ketanserin, was synthesized and tested for in vitro labeling of serotonin-S2 receptors. The compound showed a very high affinity for both membrane-bound and detergent-solubilized serotonin-S2 receptors with KD values of 0.35 and 2.03 nM, respectively. At nanomolar concentrations, binding to serotonin-S1 sites was totally absent. Serotonin-S2 receptor binding was characterized by a slow dissociation and a very low nonspecific binding. In rat frontal cortex preparations, binding could be displaced by nanomolar concentrations of different serotonin antagonists and micromolar concentrations of serotonin agonists. Compounds with other pharmacological profiles were poorly or not active. Introduction of an amino function in this new radioligand led to a decreased lipophilicity. Therefore, besides being a valuable radioligand for routine binding studies, [3H]-7-aminoketanserin will probably be a good ligand for labeling serotonin-S2 receptors on intact cells.

  DOI：

  10.1021/jm00159a017

文献信息

• Phenylpiperazine derivatives and their acid addition salts
  申请人：Mitsubishi Chemical Industries Limited

  公开号：US04716161A1

  公开（公告）日：1987-12-29

  A phenylpiperazine derivative according to the present invention has the following general formula [I]: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or alkoxy group having 1 to 3 carbon atoms, or R.sup.1 and R.sup.2 or R.sup.2 and R.sup.3 together with carbon atoms to which they are attached form --O(CH.sub.2).sub.m O-- wherein m is an integer of 1 to 3, or either R.sup.1 or R.sup.2 is amine residue selected from the group consisting of --NH.sub.2 , --NHSO.sub.2 CH.sub.3, --NHCOCH.sub.3 and --NHCONH.sub.2 and the other is hydrogen or alkoxy group of 1 to 3 carbon atoms and R.sup.3 is hydrogen; R.sup.4 and R.sup.5 are independently hydrogen or alkyl group of 1 to 3 carbon atoms; Y is --CO-- or --SO.sub.2 -- provided that at least one of R.sup.1 and R.sup.2 is not hydrogen when Y is --CO--; and n is an integer of 2 to 4. An acid addition salt of the phenylpiperazine derivative having the general formula [I] is included in the present invention. The phenylpiperazine derivative as well as its acid addition salt according to the present invention have the ability to reduce the blood pressure.

  根据本发明，苯基哌嗪衍生物具有以下通用式[I]：##STR1## 其中R.sup.1、R.sup.2和R.sup.3独立地表示氢或具有1至3个碳原子的烷氧基，或者R.sup.1和R.sup.2或R.sup.2和R.sup.3与它们所附着的碳原子一起形成--O(CH.sub.2).sub.m O--，其中m为1至3的整数，或者R.sup.1或R.sup.2中的一个是选自--NH.sub.2、--NHSO.sub.2 CH.sub.3、--NHCOCH.sub.3和--NHCONH.sub.2的氨基残基，另一个是具有1至3个碳原子的氢或烷氧基，而R.sup.3为氢；R.sup.4和R.sup.5独立地表示氢或具有1至3个碳原子的烷基；Y为--CO--或--SO.sub.2 --，但当Y为--CO--时，至少R.sup.1和R.sup.2中的一个不是氢；n为2至4的整数。本发明还包括具有通用式[I]的苯基哌嗪衍生物的酸加成盐。根据本发明，苯基哌嗪衍生物及其酸加成盐具有降低血压的能力。
• US4716161A
  申请人：——

  公开号：US4716161A

  公开（公告）日：1987-12-29
• In vitro labeling of serotonin-S2 receptors. Synthesis and binding characteristics of [3H]-7-aminoketanserin
  作者：Walter Wouters、Cornelus G. M. Janssen、Jacky Van Dun、Jos B. A. Thijssen、Pierre M. Laduron

  DOI：10.1021/jm00159a017

  日期：1986.9

  [3H]-7-Aminoketanserin (7-amino-3-[2-[4-(2-tritio-4-fluorobenzoyl)-1- piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione), an amino derivative of the selective serotonin-S2 antagonist ketanserin, was synthesized and tested for in vitro labeling of serotonin-S2 receptors. The compound showed a very high affinity for both membrane-bound and detergent-solubilized serotonin-S2 receptors with KD values of 0.35 and 2.03 nM, respectively. At nanomolar concentrations, binding to serotonin-S1 sites was totally absent. Serotonin-S2 receptor binding was characterized by a slow dissociation and a very low nonspecific binding. In rat frontal cortex preparations, binding could be displaced by nanomolar concentrations of different serotonin antagonists and micromolar concentrations of serotonin agonists. Compounds with other pharmacological profiles were poorly or not active. Introduction of an amino function in this new radioligand led to a decreased lipophilicity. Therefore, besides being a valuable radioligand for routine binding studies, [3H]-7-aminoketanserin will probably be a good ligand for labeling serotonin-S2 receptors on intact cells.