Benzene, 5-(3-bromopropoxy)-1,2,3-trimethoxy- | 204979-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Benzene, 5-(3-bromopropoxy)-1,2,3-trimethoxy-
• 英文别名: 5-(3-bromopropoxy)-1,2,3-trimethoxybenzene
• CAS: 204979-20-4
• 化学式: C₁₂H₁₇BrO₄
• 分子量: 305.169
• InChiKey: NBMXGXQPMNZIQU-UHFFFAOYSA-N

物化性质

• 沸点：
  378.4±42.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzene, 5-(3-bromopropoxy)-1,2,3-trimethoxy- 在 盐酸 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Phenoxypropoxybiguanides, Prodrugs of DHFR−Inhibiting Diaminotriazine Antimalarials

  摘要：

  A total of 34 analogues of the biguanide PS-15 (5s), a prodrug of the diaminotriazine WR99210 (8s), have been prepared. Several of them, such as 5b (PS-33) and 5m. (PS-26), maintain or exceed the in vivo activity of PS-15 while not requiring the use of highly regulated starting materials. The putative diaminotriazine metabolites of these new analogues (compounds 8) have also been prepared and shown to maintain the activity against resistant P. falciparum strains. The structure-activity relationships of biguanides 5 and putative metabolites 8 are discussed.

  DOI：

  10.1021/jm010089z
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 、 1,3-二溴丙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 Benzene, 5-(3-bromopropoxy)-1,2,3-trimethoxy-
  参考文献：
  名称：

  （+/-）-2-（3-哌啶基）-1,2,3,4-四氢异喹啉是一类新型的特异性缓动性心脏病。

  摘要：

  制备了一系列（+/-）-2-（3-哌啶基）-1，2，3，4-四氢异喹啉，并在分离的豚鼠右心房和麻醉大鼠中检查了它们的心动过缓。对母体化合物1的苄基部分进行的修饰导致将化合物11e鉴定为有效的特定缓激药。

  DOI：

  10.1016/s0960-894x(03)00349-4

文献信息

• Synthesis and Pharmacological Evaluation of 1-Oxo-2-(3-piperidyl)-1,2,3,4- tetrahydroisoquinolines and Related Analogues as a New Class of Specific Bradycardic Agents Possessing I_f Channel Inhibitory Activity
  作者：Hideki Kubota、Akio Kakefuda、Toshihiro Watanabe、Noe Ishii、Koichi Wada、Noriyuki Masuda、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1021/jm0301742

  日期：2003.10.1

  A series of 1-oxo-2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinolines and related analogues were prepared and evaluated for their bradycardic activities in isolated right atrium and in anesthetized rats. (+/-)-6,7-Dimethoxy-2-1-[3-(3,4-methylenedioxyphenoxy)propyl]-3-piperidyl}-1,2,3,4-tetrahydroisoquinoline (4) was chosen as a lead, and structural modifications were performed on the tetrahydroisoquinoline ring and the terminal aromatic ring. The modifications on the tetrahydroisoquinoline ring revealed that the 1-oxo-1,2,3,4-tetrahydroisoquinoline ring system was optimum structure for both in vitro potency and in vivo efficacy. Furthermore, methoxy, ethoxy, and methoxycarbonyl groups were identified as preferable substituents on the terminal aromatic ring. One of the 1-oxo-1,2,3,4-tetrahydroisoquinoline derivatives, (R)-10a, was further evaluated for its bradycardic activity and inhibitory activity against I-f currents. Compound (R)-10a demonstrated potent bradycardic activity in rats with minimal influence on blood pressure after oral administration. The compound also showed inhibition of I-f currents (IC50 = 0.32 muM) in guinea pig pacemaker cells.
• Phenoxypropoxybiguanides, Prodrugs of DHFR−Inhibiting Diaminotriazine Antimalarials
  作者：Norman P. Jensen、Arba L. Ager、Robert A. Bliss、Craig J. Canfield、Barbara M. Kotecka、Karl H. Rieckmann、Jacek Terpinski、David P. Jacobus

  DOI：10.1021/jm010089z

  日期：2001.11.1

  A total of 34 analogues of the biguanide PS-15 (5s), a prodrug of the diaminotriazine WR99210 (8s), have been prepared. Several of them, such as 5b (PS-33) and 5m. (PS-26), maintain or exceed the in vivo activity of PS-15 while not requiring the use of highly regulated starting materials. The putative diaminotriazine metabolites of these new analogues (compounds 8) have also been prepared and shown to maintain the activity against resistant P. falciparum strains. The structure-activity relationships of biguanides 5 and putative metabolites 8 are discussed.
• (±)-2-(3-Piperidyl)-1,2,3,4-tetrahydroisoquinolines as a new class of specific bradycardic agents
  作者：Hideki Kubota、Akio Kakefuda、Toshihiro Watanabe、Yasuko Taguchi、Noe Ishii、Noriyuki Masuda、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/s0960-894x(03)00349-4

  日期：2003.7

  A series of (+/-)-2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinolines were prepared and their bradycardic activities were examined in isolated guinea-pigs' right atria and in anesthetized rats. Modifications on the benzyl moiety of the parent compound, 1, led to the identification of compound 11e as a potent and specific bradycardic agent.

  制备了一系列（+/-）-2-（3-哌啶基）-1，2，3，4-四氢异喹啉，并在分离的豚鼠右心房和麻醉大鼠中检查了它们的心动过缓。对母体化合物1的苄基部分进行的修饰导致将化合物11e鉴定为有效的特定缓激药。