haplaphine | 54357-78-7

• 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: haplaphine
• 英文别名: 4-(3-Methylbut-2-enoxy)quinolin-2-ol；4-(3-methylbut-2-enoxy)-1H-quinolin-2-one
• CAS: 54357-78-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: OMAQSBSTRQMNRM-UHFFFAOYSA-N

物化性质

• 沸点：
  436.5±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  haplaphine 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以67%的产率得到2,4-bis(3-methylbut-2-enyloxy) quinoline
  参考文献：
  名称：

  Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols

  摘要：

  Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1(NL4.3) virus by p24 antigen capture ELISA assay. The compounds 1 and 2 showed potent inhibitory activity with IC50 value of 2.99 and 3.80 mu M, respectively. Further, 45 alkylated derivatives of quinoline 2,4-diol were synthesized and tested for anti-HIV potential in human CD4+ T cell line CEM-GFP. Among these, 13 derivatives have shown more than 60% inhibition. We have identified three most potent inhibitors 6, 9 and 23; compound 6 was found to be more potent than lead molecule 1 with IC50 value of 2.35 mu M and had better therapeutic index (26.64) as compared to AZT (23.07). Five derivatives 7, 19a, 19d, 21 and 24 have displayed good noticeable anti-HIV activity. All active compounds showed higher CC50 values which indicate that they have better therapeutic indices. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.015
• 作为产物：
  描述：

  2,4-喹啉二醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以80%的产率得到haplaphine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols

  摘要：

  Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1(NL4.3) virus by p24 antigen capture ELISA assay. The compounds 1 and 2 showed potent inhibitory activity with IC50 value of 2.99 and 3.80 mu M, respectively. Further, 45 alkylated derivatives of quinoline 2,4-diol were synthesized and tested for anti-HIV potential in human CD4+ T cell line CEM-GFP. Among these, 13 derivatives have shown more than 60% inhibition. We have identified three most potent inhibitors 6, 9 and 23; compound 6 was found to be more potent than lead molecule 1 with IC50 value of 2.35 mu M and had better therapeutic index (26.64) as compared to AZT (23.07). Five derivatives 7, 19a, 19d, 21 and 24 have displayed good noticeable anti-HIV activity. All active compounds showed higher CC50 values which indicate that they have better therapeutic indices. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.015

文献信息

• Eine einfache Darstellung von Khaplofolin, Dihydroflindersin und verwandten Alkaloiden [1] / Synthesis of Khaplofoline, Dihydroflindersine and Related Alkaloids [1]
  作者：J. Reisch、M. Müller、I. Mester

  DOI：10.1515/znb-1981-0924

  日期：1981.9.1

  A simple synthesis of khaplofoline (lb) and dihydroflindersine (4) has been reported. PTC-prenylation of 4-hydroxy-2-quinolone (8 a) gave a mixture of C-, O-and C/O-prenylated compounds (2a, 8b, 8c, 3d, 3e and 8f), 2a being the major product. N-prenylation of 8h gave 3i which yielded 8k after following treatment with aqueous HCl. Acid catalysed cyclisation of 2 a gave a mixture of 4 and 1 b in a ratio of 3:1.

  一个简单的合成khaplofoline（lb）和dihydroflindersine（4）的方法已经报道。对4-羟基-2-喹啉酮（8a）进行PTC-异戊烯基化反应得到了一系列C-、O-和C/O-异戊烯基化化合物（2a、8b、8c、3d、3e和8f），其中2a是主要产物。对8h进行N-异戊烯基化反应得到3i，随后经过水合HCl处理得到8k。对2a进行酸催化环化反应得到了4和1b的混合物，比例为3:1。