2-(3-chloropropoxy)-1,1'-biphenyl | 107352-45-4

• 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-(3-chloropropoxy)-1,1'-biphenyl
• 英文别名: biphenyl-2-yl-(3-chloro-propyl)-ether；3-Chlor-1-(biphenylyl-(2)-oxy)-propan；Biphenyl-2-yl-(3-chlor-propyl)-aether；2-(3-Chlor-propyloxy)-biphenyl；3-(Biphenylyl-(2)-oxy)-propylchlorid；1-(3-Chloropropoxy)-2-phenylbenzene
• CAS: 107352-45-4
• 化学式: C₁₅H₁₅ClO
• mdl: MFCD11126917
• 分子量: 246.737
• InChiKey: PVPVHHGDYSDKJS-UHFFFAOYSA-N

物化性质

• 沸点：
  353.5±17.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  咪唑 、 2-(3-chloropropoxy)-1,1'-biphenyl 在 sodium hydride 作用下， 生成 1-<3-(<1,1'-biphenyl>-2-yloxy)propyl>-1H-imidazole
  参考文献：
  名称：

  Imidazole anticonvulsants: structure-activity relationships of [(biphenylyloxy)alkyl]imidazoles

  摘要：

  The [(biphenylyloxy)alkyl]imidazoles were found to be potent anticonvulsants. The most potent compound of the series, 1-[2- ([1,1'-biphenyl]-2-yloxy)ethyl]-1H-imidazole (4), had an ED50 of 15.5 mg/kg against maximal-electroshock-induced seizures in mice after oral administration; the horizontal screen ED50 was 320 mg/kg, revealing that the compound has a protective index of 21. Homologues bearing three- and four-carbon tethers between the imidazole and biphenylyloxy moieties were also active, but their potency was attenuated relative to 4. Congeners with the imidazolylalkoxy moiety at the meta or para positions of biphenyl were also less active. All these compounds were potent potentiators of hexobarbital-induced sleeping time in mice, presumably via the well-known imidazole-mediated inhibition of cytochrome P-450. The structural features governing the anticonvulsant and sleeping-time activities appear to be distinct, but a complete dissociation of these two effects has not been achieved. Thus, the potential of these compounds as clinically useful antiepileptic drugs would appear to be limited.

  DOI：

  10.1021/jm00388a035
• 作为产物：
  描述：

  1-氯-3-碘丙烷 、 邻苯基苯酚 在 sodium hydride 作用下， 生成 2-(3-chloropropoxy)-1,1'-biphenyl
  参考文献：
  名称：

  Imidazole anticonvulsants: structure-activity relationships of [(biphenylyloxy)alkyl]imidazoles

  摘要：

  The [(biphenylyloxy)alkyl]imidazoles were found to be potent anticonvulsants. The most potent compound of the series, 1-[2- ([1,1'-biphenyl]-2-yloxy)ethyl]-1H-imidazole (4), had an ED50 of 15.5 mg/kg against maximal-electroshock-induced seizures in mice after oral administration; the horizontal screen ED50 was 320 mg/kg, revealing that the compound has a protective index of 21. Homologues bearing three- and four-carbon tethers between the imidazole and biphenylyloxy moieties were also active, but their potency was attenuated relative to 4. Congeners with the imidazolylalkoxy moiety at the meta or para positions of biphenyl were also less active. All these compounds were potent potentiators of hexobarbital-induced sleeping time in mice, presumably via the well-known imidazole-mediated inhibition of cytochrome P-450. The structural features governing the anticonvulsant and sleeping-time activities appear to be distinct, but a complete dissociation of these two effects has not been achieved. Thus, the potential of these compounds as clinically useful antiepileptic drugs would appear to be limited.

  DOI：

  10.1021/jm00388a035

文献信息

• 2-, 3- And 4-biphenyloxyaminoalkanes and related compounds, their preparation and uses, and pharmaceutical compositions containing them
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0157652A1

  公开（公告）日：1985-10-09

  Compounds useful for treating inflammation, swelling and associated pain, and psoriasis, represented by the formula: and the pharmaceutically acceptable acid addition salts thereof, wherein: a is an integer of 0-3; b is an integer of 0-2; n is an integer of 3-12; each X and each Y are independently-halo, -R1, -alkoxy, or-phenyl; and B is selected from: and in which R' and R2 are independently H, alkyl or cycloalkyl; R3 is H, alkyl or -CH2CH2OH; and m is an integer of 3-8. Novel compounds are those wherein n is at least 6 if both a and b are 0.

  用于治疗炎症、肿胀及相关疼痛和牛皮癣的化合物，由式：及其药学上可接受的酸加成盐表示，其中：a 是 0-3 的整数；b 是 0-2 的整数；n 是 3-12 的整数；每个 X 和每个 Y 独立地是卤素、-R1、-烷氧基或苯基；B 选自：且其中 R' 和 R2 独立地是 H、烷基或环烷基；R3 是 H、烷基或-CH2CH2OH；且 m 是 3-8 的整数。 新型化合物是指如果 a 和 b 均为 0，则 n 至少为 6 的化合物。
• Local Anesthetics. I. Some Aryl Alkamine Ethers
  作者：Howard B. Wright、M. B. Moore

  DOI：10.1021/ja01149a106

  日期：1951.5
• Thiocyano-alkyl ethers of the phenylphenols
  申请人：DOW CHEMICAL CO

  公开号：US02185208A1

  公开（公告）日：1940-01-02
• ROBERTSON D. W.; BEEDLE E. E.; LAWSON R.; LEANDER J. D., J. MED. CHEM., 30,(1987) N 5, 939-943
  作者：ROBERTSON D. W.、 BEEDLE E. E.、 LAWSON R.、 LEANDER J. D.

  DOI：——

  日期：——
• Imidazole anticonvulsants: structure-activity relationships of [(biphenylyloxy)alkyl]imidazoles
  作者：David W. Robertson、E. E. Beedle、Ron Lawson、J. David Leander

  DOI：10.1021/jm00388a035

  日期：1987.5

  The [(biphenylyloxy)alkyl]imidazoles were found to be potent anticonvulsants. The most potent compound of the series, 1-[2- ([1,1'-biphenyl]-2-yloxy)ethyl]-1H-imidazole (4), had an ED50 of 15.5 mg/kg against maximal-electroshock-induced seizures in mice after oral administration; the horizontal screen ED50 was 320 mg/kg, revealing that the compound has a protective index of 21. Homologues bearing three- and four-carbon tethers between the imidazole and biphenylyloxy moieties were also active, but their potency was attenuated relative to 4. Congeners with the imidazolylalkoxy moiety at the meta or para positions of biphenyl were also less active. All these compounds were potent potentiators of hexobarbital-induced sleeping time in mice, presumably via the well-known imidazole-mediated inhibition of cytochrome P-450. The structural features governing the anticonvulsant and sleeping-time activities appear to be distinct, but a complete dissociation of these two effects has not been achieved. Thus, the potential of these compounds as clinically useful antiepileptic drugs would appear to be limited.