(2-azido-3-phenylmethoxypropoxy)methylbenzene | 156536-19-5

• 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: (2-azido-3-phenylmethoxypropoxy)methylbenzene
• CAS: 156536-19-5
• 化学式: C₁₇H₁₉N₃O₂
• 分子量: 297.357
• InChiKey: ZWVZKHOAYFRUGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.22
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2-azido-3-phenylmethoxypropoxy)methylbenzene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1,3-bis(benzyloxy)propan-2-amine
  参考文献：
  名称：

  A New Water-soluble p-Boronophenylalanine Derivative for Neutron Capture Therapy

  摘要：

  我们合成了一种对硼苯丙氨酸（BPA）衍生物，它的水溶性比 BPA 本身高出约一千倍，而且与肿瘤/正常细胞的结合率也更高。

  DOI：

  10.1246/cl.1993.465
• 作为产物：
  描述：

  1,3-双(苄氧基)-2-丙醇 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2-azido-3-phenylmethoxypropoxy)methylbenzene
  参考文献：
  名称：

  A New Water-soluble p-Boronophenylalanine Derivative for Neutron Capture Therapy

  摘要：

  我们合成了一种对硼苯丙氨酸（BPA）衍生物，它的水溶性比 BPA 本身高出约一千倍，而且与肿瘤/正常细胞的结合率也更高。

  DOI：

  10.1246/cl.1993.465

文献信息

• β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives
  作者：Thomas Storz、Bruno Bernet、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2380::aid-hlca2380>3.0.co;2-p

  日期：1999.12.15

  The D-manno-configured N-anisylated beta-lactam 40, the beta-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene: from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the beta-lactam amino acid 43, besides its hydrolysis product 44. Reductive N-acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-beta-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-beta-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected beta-lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).
• Synthesis and Biological Properties of Water-Soluble p-Boronophenylalanine Derivatives. Relationship between Water Solubility, Cytotoxicity, and Cellular Uptake
  作者：Hisao Nemoto、Jianping Cai、Satoshi Iwamoto、Yoshinori Yamamoto

  DOI：10.1021/jm00010a012

  日期：1995.5

  Water-soluble p-boronophenylalanine (BPA) derivatives having cascade polyols, the monohydroxy derivative BPA(OH) (4), the dihydroxy analogue BPA(OH)(2) (5), and the tetrahydroxy analogue BPA(OH)(4) (6), were synthesized in order to elucidate a relationship between the molecular structures and the cellular uptake. Biological properties of these compounds in addition to BPA (1) itself were investigated. Water solubility increased in the order of BPA < BPA(OH) less than or equal to BPA(OH)(2) < BPA(OH)(4). Cytotoxicity to B-16 melanoma and TIG hybrobrast cells decreased in the order of BPA >> BPA(OH) greater than or equal to BPA(OH)(2) > BPA(OH)(4). The cellular uptake by both B-16 and TIG cells decreased in the order of BPA >> BPA(OH) greater than or equal to BPA(OH)2 > BPA(OH)4, whereas the uptake ratio of B-16/TIG increased in the order of BPA < BPA(OH) less than or equal to BPA(OH)(2) < BPA(OH)(4). The latter ratio indicates the selectivity on the uptake by a cancer to normal cell.