(S)-9-chloro-3-ethoxy-1-methyl-1,4-dihydro-6H-pyrazino[2,1-b]quinazolin-6-one | 1118645-16-1

• 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: (S)-9-chloro-3-ethoxy-1-methyl-1,4-dihydro-6H-pyrazino[2,1-b]quinazolin-6-one
• CAS: 1118645-16-1
• 化学式: C₁₄H₁₄ClN₃O₂
• 分子量: 291.737
• InChiKey: WSPQINBQMKDNPB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.48
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-9-chloro-3-ethoxy-1-methyl-1,4-dihydro-6H-pyrazino[2,1-b]quinazolin-6-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 0.5h， 以79%的产率得到9-chloro-3-ethoxy-1-methyl-6H-pyrazino[2,1-b]quinazolin-6-one
  参考文献：
  名称：

  Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors

  摘要：

  The gamma-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the development of a safer insecticide. In an attempt to obtain compounds with greater activity, a series of racemic alantrypinone derivatives were systematically synthesized using hetero Diels-Alder reactions, and a total of34 compounds were examined for their ability to inhibit the specific binding of [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate, a high-affinity non-competitive antagonist, to housefly-head membranes. The assay results showed that (1) there is no significant difference between the potencies of natural (+)-alantrypinone and its synthetic racemate; (2) the amide NHs at the 2- and 18-positions are important for high activity; (3) there is a considerable drop in potency for compounds without an aromatic ring at the 16-position; and (4) a large substituent at the 3-position is detrimental to high activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.017
• 作为产物：
  描述：

  (S)-9-chloro-1-methyl-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3,6(4H)-dione 、 triethyloxonium fluoroborate 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以41%的产率得到(S)-9-chloro-3-ethoxy-1-methyl-1,4-dihydro-6H-pyrazino[2,1-b]quinazolin-6-one
  参考文献：
  名称：

  Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors

  摘要：

  The gamma-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the development of a safer insecticide. In an attempt to obtain compounds with greater activity, a series of racemic alantrypinone derivatives were systematically synthesized using hetero Diels-Alder reactions, and a total of34 compounds were examined for their ability to inhibit the specific binding of [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate, a high-affinity non-competitive antagonist, to housefly-head membranes. The assay results showed that (1) there is no significant difference between the potencies of natural (+)-alantrypinone and its synthetic racemate; (2) the amide NHs at the 2- and 18-positions are important for high activity; (3) there is a considerable drop in potency for compounds without an aromatic ring at the 16-position; and (4) a large substituent at the 3-position is detrimental to high activity. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.017