1-(2-喹噁啉)-1,2,3,4-丁四醇 | 80840-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 1-(2-喹噁啉)-1,2,3,4-丁四醇
• 中文别名: 赤藓醇I又称为1,2,3,4-丁四醇；1-（2-喹喔啉基）-1,2,3,4-丁四醇
• 英文名称: tetrahydroxybutyl quinoxaline
• 英文别名: tetra-oxy-butylo-quinoxaline；1-quinoxalin-2-yl-butane-1,2,3,4-tetraol；D-(1R)-1-quinoxalin-2-yl-erythritol；3-Chinoxalinyl-butantetrol；1-(2-Quinoxalinyl)-1,2,3,4-butanetetrol；1-quinoxalin-2-ylbutane-1,2,3,4-tetrol
• CAS: 80840-09-1
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: JNOHSLKLTQNYAD-UHFFFAOYSA-N

物化性质

• 熔点：
  >160°C (dec.)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 储存条件：
  2-8°C

制备方法与用途

生物活性分子1-(2-喹诺林基)-1,2,3,4-丁四醇是一种内源性代谢物。印迹聚合物 P-1 对该化合物具有显著的亲和力。

反应信息

• 作为反应物：
  描述：

  1-(2-喹噁啉)-1,2,3,4-丁四醇 在 双氧水 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 5.0h， 以50%的产率得到2-喹喔啉羧酸
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel quinoxalin-2-carboxamides as 5-HT3 receptor antagonists for the management of depression

  摘要：

  A novel series of quinoxalin-2-carboxamides were designed based on the ligand-based approach, employing a three-point pharmacophore model; it consists of an aromatic residue and a linking carbonyl group and a basic nitrogen. The target new chemical entities were synthesized from the key intermediate, quinoxalin-2-carboxylic acid, by coupling it with various amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC center dot HCl) and 1-hydroxybenzotriazole (HOBt). The obtained compounds' structures were confirmed by spectral data. The target new chemical entities were evaluated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT3 agonist, 2-methyl-5-HT, which was expressed in the form of pA(2) value. All the synthesized compounds showed antagonism towards 5-HT3 receptor; based on this result, a structure-activity relationship was derived, which reveals that the aromatic residue in 5-HT3 receptor antagonists may have hydrophobic interaction with 5-HT3 receptor. Regardless of their antagonistic potentials, all the synthesized molecules were screened for their anti-depressant potentials by using forced swim test in mice model; interestingly none of the tested compounds affect the locomotion of mice in the tested dose levels. Compounds with significant pA(2) values exhibited good anti-depressant-like activity as compared to the vehicle-treated group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.128
• 作为产物：
  描述：

  果糖 、 邻苯二胺 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 18.0h， 以45%的产率得到1-(2-喹噁啉)-1,2,3,4-丁四醇
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel quinoxalin-2-carboxamides as 5-HT3 receptor antagonists for the management of depression

  摘要：

  A novel series of quinoxalin-2-carboxamides were designed based on the ligand-based approach, employing a three-point pharmacophore model; it consists of an aromatic residue and a linking carbonyl group and a basic nitrogen. The target new chemical entities were synthesized from the key intermediate, quinoxalin-2-carboxylic acid, by coupling it with various amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC center dot HCl) and 1-hydroxybenzotriazole (HOBt). The obtained compounds' structures were confirmed by spectral data. The target new chemical entities were evaluated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT3 agonist, 2-methyl-5-HT, which was expressed in the form of pA(2) value. All the synthesized compounds showed antagonism towards 5-HT3 receptor; based on this result, a structure-activity relationship was derived, which reveals that the aromatic residue in 5-HT3 receptor antagonists may have hydrophobic interaction with 5-HT3 receptor. Regardless of their antagonistic potentials, all the synthesized molecules were screened for their anti-depressant potentials by using forced swim test in mice model; interestingly none of the tested compounds affect the locomotion of mice in the tested dose levels. Compounds with significant pA(2) values exhibited good anti-depressant-like activity as compared to the vehicle-treated group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.128

文献信息

• Cationic porphyrin–quinoxaline conjugate as a photochemically triggered novel cytotoxic agent
  作者：Dalip Kumar、K.P. Chandra Shekar、Bhupendra Mishra、Ryohsuke Kurihara、Maiko Ogura、Takeo Ito

  DOI：10.1016/j.bmcl.2013.03.126

  日期：2013.6

  A novel cationic porphyrin-quinoxaline conjugate 8 was prepared in good yield by the coupling of activated quinoxaline carboxylic acid 5 with an appropriate aminoporphyrin. The UV-vis spectra of conjugate 8 with the addition of ctDNA shows substantial hypochromicity (39%) and a red shift (12 nm) in the Soret band indicating intercalation and self stacking along the surface. The binding constant of conjugate 8 with ctDNA was determined to be 1.26 x 106 M-1. The porphyrin-quinoxaline conjugate 8 displayed enhanced photocytotoxicity (IC50 = 0.06 mu M) when compared to TMPyP against A549 cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.
• Palios, G.; Guskos, N.; Likodimos, V., Polish Journal of Chemistry, 1994, vol. 68, # 12, p. 2519 - 2528
  作者：Palios, G.、Guskos, N.、Likodimos, V.、Paraskevas, S. M.、Savvogias, S.、et al.

  DOI：——

  日期：——
• Design, synthesis and structure–activity relationship of novel quinoxalin-2-carboxamides as 5-HT3 receptor antagonists for the management of depression
  作者：Radhakrishnan Mahesh、Thangaraj Devadoss、Dilip Kumar Pandey、Shvetank Bhatt、Shushil Kumar Yadav

  DOI：10.1016/j.bmcl.2010.08.128

  日期：2010.11

  A novel series of quinoxalin-2-carboxamides were designed based on the ligand-based approach, employing a three-point pharmacophore model; it consists of an aromatic residue and a linking carbonyl group and a basic nitrogen. The target new chemical entities were synthesized from the key intermediate, quinoxalin-2-carboxylic acid, by coupling it with various amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC center dot HCl) and 1-hydroxybenzotriazole (HOBt). The obtained compounds' structures were confirmed by spectral data. The target new chemical entities were evaluated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT3 agonist, 2-methyl-5-HT, which was expressed in the form of pA(2) value. All the synthesized compounds showed antagonism towards 5-HT3 receptor; based on this result, a structure-activity relationship was derived, which reveals that the aromatic residue in 5-HT3 receptor antagonists may have hydrophobic interaction with 5-HT3 receptor. Regardless of their antagonistic potentials, all the synthesized molecules were screened for their anti-depressant potentials by using forced swim test in mice model; interestingly none of the tested compounds affect the locomotion of mice in the tested dose levels. Compounds with significant pA(2) values exhibited good anti-depressant-like activity as compared to the vehicle-treated group. (C) 2010 Elsevier Ltd. All rights reserved.