5-[3-(4-(2-quinolylmethyloxy)phenoxy)propyl]tetrazole | 107813-78-5

• 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: 5-[3-(4-(2-quinolylmethyloxy)phenoxy)propyl]tetrazole
• 英文别名: 2-{4-[3-(1H-Tetrazol-5-yl)-propoxy]-phenoxymethyl}-quinoline；2-[[4-[3-(2H-tetrazol-5-yl)propoxy]phenoxy]methyl]quinoline
• CAS: 107813-78-5
• 化学式: C₂₀H₁₉N₅O₂
• 分子量: 361.403
• InChiKey: SQQTUVOFASOKGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-苄氧基苯酚 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 氢气 、 potassium carbonate 、 氯化铵 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 40.0~140.0 ℃ 、310.27 kPa 条件下， 反应 52.5h， 生成 5-[3-(4-(2-quinolylmethyloxy)phenoxy)propyl]tetrazole
  参考文献：
  名称：

  Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 1. Initial structure-activity relationships

  摘要：

  This series of reports describes the development of orally active, highly potent, specific antagonists of the peptidoleukotrienes containing a (2-quinolinylmethoxy)phenyl moiety. Described in this first report are the structure-activity relationships that led to a more than a 20-fold improvement of the potency and selectivity of the initial chemical lead (RG 5901). From this series of compounds, RG 7152 (16) was identified and selected for further evaluation in the clinic as an antiasthmatic agent. Compound 16 competitively inhibits [3H]LTD4 binding to membranes from guinea pig lung (Ki = 38 +/- 6 nM) and the spasmogenic activity of LTC4, LTD4, and LTE4 in parenchymal lung strips from guinea pigs. Unlike the original lead (RG 5901), compound 16 does not inhibit 5-lipoxygenase from guinea pig PMNs. Following oral administration to guinea pigs, 16 blocks LTD4-induced dermal permeability (ED50 = 6.9 mg/kg), LTD4-induced bronchoconstriction (ED50 = 1.1 mg/kg), antigen-induced bronchoconstriction (ED50 = 2.5 mg/kg), and anaphylactic-induced mortality (ED50 = 16 mg/kg). These studies on structure-activity relationships indicate that there is a requirement for an acidic function and the presence of the (2-quinolinylmethoxy)phenyl moiety in a specific geometric arrangement.

  DOI：

  10.1021/jm00166a016

文献信息

• Quinolinyl ether or thioether tetrazoles as agents for the treatment of
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04874769A1

  公开（公告）日：1989-10-17

  This invention relates to certain quinolyl ether and thioether tetrazoles and their use as valuable pharmaceutical agents for the treatment of hypersensitive ailments, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and antiallergic properties.

  这项发明涉及某些喹诺醚和硫醚四唑，以及它们作为有价值的药用剂治疗过敏病症的用途，特别是作为脂氧合酶抑制剂和/或白三烯拮抗剂，具有抗炎和抗过敏特性。
• Aryl and heteroaryl ethers as agents for the treatment of hypersensitive
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04839369A1

  公开（公告）日：1989-06-13

  Aryl and Heteroaryl Ethers are used for their anti-inflammatory and anti-allergic properties.

  芳基和杂芳基醚因其抗炎和抗过敏特性而被使用。
• Aryl and heteroaryl ethers as agents for the treatment of hypersensitive aliments
  申请人：USV PHARMACEUTICAL CORPORATION

  公开号：EP0200101A2

  公开（公告）日：1986-12-10

  The present invention is concerned with the therapeutic composition comprising as an active ingredient a compound of the formula: and salts thereof; wherein Ar and Ar, are independently phenyl, naphthyl or a nitrogen, oxygen, or sulfur heterocyclic ring; R,, R2 and R3 are independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, alkyl carboxy, carboxy, formyl, lower alkyl carbonyl, aryl, aryloxy, benzyloxy, lower alkylamino, diloweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, nitro, amino, tetrahydropyranylmethyl, tetrazole, tetrazole lower alkyl, formyl amino or lower alkanoylamino; R, is independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, alkyl carboxy, carboxy, formyl, lower alkyl carbonyl, aryl, aryloxy, benzyloxy, lower alkylamino, diloweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, nitro, amino, tetrahydropyranylmethyl, or tetrazole, or tetrazole lower alkyl or Rs; Rs is lower alkoxy, phenyl, OH, CO2R6cyclic or heterocyclic structures.

  本发明涉及治疗组合物，该组合物包含作为活性成分的式化合物： 及其盐类；其中 Ar和Ar，独立地是苯基、萘基或氮、氧或硫杂环； R、R2 和 R3 独立地为 H、低级烷基、低级烷氧基、羟基、卤代、三卤甲基、羟基-低级烷基、烷基羧基、羧基、甲酰基、低级烷基羰基、芳基、芳氧基、苄氧基、低级烷基氨基、稀低级烷基氨基、氰基、烷基羰基、芳基羰基、芳氧基、苄氧基、低级烷基酰胺、稀低级烷基酰胺、低级烷基羰基下烷基羰基、芳基、芳氧基、苄氧基、下烷基氨基、稀烷基氨基、氰基、下烷酰氧基、氨基甲酰基、下烷氧基-下烷氧基、下碳烷氧基-下烷氧基、硝基、氨基、四氢吡喃甲基、四唑、四唑下烷基、甲酰氨基或下烷基氨基； R，独立地为 H、低级烷基、低级烷氧基、羟基、卤代、三卤甲基、羟基-低级烷基、烷基羧基、羧基、甲酰基、低级烷基羰基、芳基、芳氧基、苄氧基、低级烷基氨基低级烷基羰基、芳基、芳氧基、苄氧基、低级烷基氨基、稀低级烷基氨基、氰基、低级烷酰氧基、氨基甲酰基、低级烷氧基-低级烷氧基、低级碳烷氧基-低级烷氧基、硝基、氨基、四氢吡喃甲基、或四唑、或四唑低级烷基或 Rs； Rs 是低级烷氧基、苯基、OH、CO2R6 环结构或杂环结构。
• YOUSSEFYEH, RAYMOND;CHAKRABORTY, UTPAL;MAGNIEN, ERNEST;DESAI, ROHIT
  作者：YOUSSEFYEH, RAYMOND、CHAKRABORTY, UTPAL、MAGNIEN, ERNEST、DESAI, ROHIT

  DOI：——

  日期：——
• YOUSSEFYEH, RAYMOND;CNAKRABORTY, UTPAL;MAGNIEN, ERNEST;DESAI, ROHIT;LEE, +
  作者：YOUSSEFYEH, RAYMOND、CNAKRABORTY, UTPAL、MAGNIEN, ERNEST、DESAI, ROHIT、LEE, +

  DOI：——

  日期：——