1-(3-(bromomethyl)phenoxy)heptane | 251636-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-(bromomethyl)phenoxy)heptane
• 英文别名: 1-(bromomethyl)-3-(heptyloxy)benzene；1-(Bromomethyl)-3-heptoxybenzene
• CAS: 251636-51-8
• 化学式: C₁₄H₂₁BrO
• 分子量: 285.224
• InChiKey: TVFVCRLHQRRHQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-(bromomethyl)phenoxy)heptane 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.08h， 生成 2-amino-4-hydroxy-5-benzyl-3-heptoxy-6-methylpyrimidine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors of Trypanosomal and Leishmanial Dihydrofolate Reductase

  摘要：

  This paper concerns the design, synthesis, and evaluation of inhibitors of leishmanial and trypanosomal dihydrofolate reductase. Initially study was made of the structures of the leishmanial and human enzyme active sites to see if there were significant differences which could be exploited for selective drug design. Then a series of compounds were synthesized based on 5-benzyl-2,4-diaminopyrimidines. These compounds were assayed against the protozoan and human enzymes and showed selectivity for the protozoan enzymes. The structural data was then used to rationalize the enzyme assay data. Compounds were also tested against the clinically relevant forms of the intact parasite. Activity was seen against the trypanosomes for a number of compounds. The compounds were in general less active against Leishmania. This latter result may be due to uptake problems. Two of the compounds also showed some in vivo activity in a model of African trypanosomiasis.

  DOI：

  10.1021/jm981130+
• 作为产物：
  描述：

  1-碘庚烷 在 氢氧化钾 、 sodium tetrahydroborate 、 三溴化磷 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.33h， 生成 1-(3-(bromomethyl)phenoxy)heptane
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors of Trypanosomal and Leishmanial Dihydrofolate Reductase

  摘要：

  This paper concerns the design, synthesis, and evaluation of inhibitors of leishmanial and trypanosomal dihydrofolate reductase. Initially study was made of the structures of the leishmanial and human enzyme active sites to see if there were significant differences which could be exploited for selective drug design. Then a series of compounds were synthesized based on 5-benzyl-2,4-diaminopyrimidines. These compounds were assayed against the protozoan and human enzymes and showed selectivity for the protozoan enzymes. The structural data was then used to rationalize the enzyme assay data. Compounds were also tested against the clinically relevant forms of the intact parasite. Activity was seen against the trypanosomes for a number of compounds. The compounds were in general less active against Leishmania. This latter result may be due to uptake problems. Two of the compounds also showed some in vivo activity in a model of African trypanosomiasis.

  DOI：

  10.1021/jm981130+

文献信息

• Discovery of a novel activator of 5-lipoxygenase from an anacardic acid derived compound collection
  作者：Rosalina Wisastra、Petra A.M. Kok、Nikolaos Eleftheriadis、Matthew P. Baumgartner、Carlos J. Camacho、Hidde J. Haisma、Frank J. Dekker

  DOI：10.1016/j.bmc.2013.10.015

  日期：2013.12

  human 5-LOX. This compound showed both non-competitive activation towards the human 5-LOX activator adenosine triphosphate (ATP) and non-essential mixed type activation against the substrate linoleic acid, while having no effect on the conversion of the substrate arachidonic acid. The kinetic analysis demonstrated a non-essential activation of the linoleic acid conversion with a KA of 8.65 μM, αKA of

  脂肪氧化酶 (LOX) 和环氧合酶 (COX) 将多不饱和脂肪酸代谢为炎症信号分子。调节这些酶的活性可能为治疗炎性疾病提供新方法。在这项研究中，我们筛选了新型漆树酸衍生物作为人类 5-LOX 和 COX-2 活性的调节剂。有趣的是，一种新型的水杨酸衍生物23a被鉴定为人 5-LOX 的一种令人惊讶的有效激活剂。该化合物显示出对人 5-LOX 激活剂三磷酸腺苷 (ATP) 的非竞争性激活和对底物亚油酸的非必需混合型激活，同时对底物花生四烯酸的转化没有影响。动力学分析证明了亚油酸转化的非必要激活，其K A为 8.65 μM，αK A为 0.38 μM，β值为 1.76。同样有趣的是，一个可比较的导数23d显示出对亚油酸转化的混合型抑制作用。这些观察结果表明人 5-LOX 中存在不同于 ATP 结合位点的变构结合位点。与花生四烯酸相比，23a和23d对亚油酸转化的激活和抑制行为通过对接研究合理化
• Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings
  作者：Satoshi Yamauchi、Tuti Wukirsari、Yoshiaki Ochi、Hisashi Nishiwaki、Kosuke Nishi、Takuya Sugahara、Koichi Akiyama、Taro Kishida

  DOI：10.1016/j.bmcl.2017.06.070

  日期：2017.9

  lignano-9,9′-lactones (α,β-dibenzyl-γ-butyrolactone lignans), which showed the higher cytotoxicity than arctigenin, were synthesized. The well-known cytotoxic arctigenin showed activity against HL-60 cells (EC50 = 12 μM), however, it was inactive against HeLa cells (EC50 > 100 μM). The synthesized (3,4-dichloro, 2′-butoxy)-derivative 55 and (3,4-dichloro, 4′-butyl)-derivative 66 bearing the lignano-9

  合成了新的木质素-9,9'-内酯（α，β-二苄基-γ-丁内酯木脂素），其细胞毒性高于arctigenin。众所周知的细胞毒性artigenin对HL-60细胞具有活性（EC 50  = 12μM），但是对HeLa细胞没有活性（EC 50  > 100μM）。具有木质素-9,9'-内酯结构的合成的（3,4-二氯，2'-丁氧基）衍生物55和（3,4-二氯，4'-丁基）衍生物66的EC 50值为分别针对HL-60细胞10μM和9.4μM。对于HeLa细胞，衍生物66的EC 50值为27μM。通过将活性与相应的9,9'-环氧结构（四氢呋喃化合物）进行比较，表明了55和66的内酯结构对于更高活性的重要性。木质素9,9'-内酯芳香环上的取代基影响细胞毒性水平，差异超过10倍。
• Design, Synthesis, and Evaluation of Inhibitors of Trypanosomal and Leishmanial Dihydrofolate Reductase
  作者：Shafinaz F. Chowdhury、Victor Bernier Villamor、Ramon Hurtado Guerrero、Isabel Leal、Reto Brun、Simon L. Croft、Jonathan M. Goodman、Louis Maes、Luis M. Ruiz-Perez、Dolores Gonzalez Pacanowska、Ian H. Gilbert

  DOI：10.1021/jm981130+

  日期：1999.10.1

  This paper concerns the design, synthesis, and evaluation of inhibitors of leishmanial and trypanosomal dihydrofolate reductase. Initially study was made of the structures of the leishmanial and human enzyme active sites to see if there were significant differences which could be exploited for selective drug design. Then a series of compounds were synthesized based on 5-benzyl-2,4-diaminopyrimidines. These compounds were assayed against the protozoan and human enzymes and showed selectivity for the protozoan enzymes. The structural data was then used to rationalize the enzyme assay data. Compounds were also tested against the clinically relevant forms of the intact parasite. Activity was seen against the trypanosomes for a number of compounds. The compounds were in general less active against Leishmania. This latter result may be due to uptake problems. Two of the compounds also showed some in vivo activity in a model of African trypanosomiasis.