GCA

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: GCA
• 英文别名: (3aS,4R,9bR)-6,8-difluoro-4-pyridin-3-yl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline
• 化学式: C₁₇H₁₄F₂N₂
• 分子量: 284.308
• InChiKey: NJZHEQOUHLZCOX-WWGRRREGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  GCA 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.25h， 以100%的产率得到(3aS,4R,9bR)-6,8-difluoro-4-pyridin-3-yl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline
  参考文献：
  名称：

  Distinct biological effects of golgicide a derivatives on larval and adult mosquitoes

  摘要：

  A collection of Golgicide A (GCA) analogs has been synthesized and evaluated in larval and adult mosquito assays. Commercially available GCA is a mixture of four compounds. One enantiomer (GCA-2) of the major diastereomer in this mixture was shown to be responsible for the unique activity of GCA. Structure-activity studies (SAR) of the GCA architecture suggested that the pyridine ring was most easily manipulated without loss or gain in new activity. Eighteen GCA analogs were synthesized of which five displayed distinct behavior between larval and adult mosquitos, resulting in complete mortality of both Aedes aegypti and Anopheles stephensi larvae. Two analogs from the collection were shown to be distinct from the rest in displaying high selectivity and efficiency in killing An. stephensi larvae. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.076
• 作为产物：
  描述：

  环戊二烯 在 草酸 作用下， 以 正己烷 、 异丙醇 、 乙腈 为溶剂， 反应 8.0h， 生成 GCA 、 Golgicide A-1
  参考文献：
  名称：

  Distinct biological effects of golgicide a derivatives on larval and adult mosquitoes

  摘要：

  A collection of Golgicide A (GCA) analogs has been synthesized and evaluated in larval and adult mosquito assays. Commercially available GCA is a mixture of four compounds. One enantiomer (GCA-2) of the major diastereomer in this mixture was shown to be responsible for the unique activity of GCA. Structure-activity studies (SAR) of the GCA architecture suggested that the pyridine ring was most easily manipulated without loss or gain in new activity. Eighteen GCA analogs were synthesized of which five displayed distinct behavior between larval and adult mosquitos, resulting in complete mortality of both Aedes aegypti and Anopheles stephensi larvae. Two analogs from the collection were shown to be distinct from the rest in displaying high selectivity and efficiency in killing An. stephensi larvae. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.076

文献信息

• Distinct biological effects of golgicide a derivatives on larval and adult mosquitoes
  作者：Daniel J. Mack、Jun Isoe、Roger L. Miesfeld、Jon T. Njardarson

  DOI：10.1016/j.bmcl.2012.06.076

  日期：2012.8

  A collection of Golgicide A (GCA) analogs has been synthesized and evaluated in larval and adult mosquito assays. Commercially available GCA is a mixture of four compounds. One enantiomer (GCA-2) of the major diastereomer in this mixture was shown to be responsible for the unique activity of GCA. Structure-activity studies (SAR) of the GCA architecture suggested that the pyridine ring was most easily manipulated without loss or gain in new activity. Eighteen GCA analogs were synthesized of which five displayed distinct behavior between larval and adult mosquitos, resulting in complete mortality of both Aedes aegypti and Anopheles stephensi larvae. Two analogs from the collection were shown to be distinct from the rest in displaying high selectivity and efficiency in killing An. stephensi larvae. (c) 2012 Elsevier Ltd. All rights reserved.