6-(2,3-epoxypropoxy)flavone | 84858-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-(2,3-epoxypropoxy)flavone
• 英文别名: 6-(Oxiran-2-ylmethoxy)-2-phenylchromen-4-one
• CAS: 84858-26-4
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: BKYCQNWTYQOALS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2,3-epoxypropoxy)flavone 、 2-methyl-4-chloro-5-(1-piperazinyl)-3(2H)-pyridazinone 以 乙醇 为溶剂， 反应 18.0h， 以60%的产率得到4-Chloro-5-{4-[2-hydroxy-3-(4-oxo-2-phenyl-4H-chromen-6-yloxy)-propyl]-piperazin-1-yl}-2-methyl-2H-pyridazin-3-one
  参考文献：
  名称：

  Design, synthesis, and α1-adrenoceptor binding properties of new arylpiperazine derivatives bearing a flavone nucleus as the terminal heterocyclic molecular portion

  摘要：

  Following our research project aimed at obtaining new compounds with high affinity and selectivity toward alpha(1)-adrenoceptors (AR), a new class of piperazine derivatives was designed, synthesized and biologically tested. The new compounds 1-13 are characterized by a flavone system linked, through an ethoxy or propoxy spacer, to a phenyl- or pyridazinone-piperazine moiety. Biological data showed an interesting profile for the phenylpiperazine subclass found to have a nanomolar affinity toward alpha(1)-AR, and less pronounced affinity for alpha(2)-AR and the 5-HT1A serotoninergic receptor. A discussion on the structure-activity relationship (SAR) of such compounds is also reported, on the basis of the flavone substitution pattern, length and functionalization of the spacer, and disruption of the phenylpiperazine system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.033
• 作为产物：
  描述：

  6-羟基黄酮 以65%的产率得到epoxypropyl ether
  参考文献：
  名称：

  Antihypertensive chromonoxypropanolamines

  摘要：

  Chromone衍生物，如6或7-(3-氨基-2-羟基丙氧基)-2-苯基色酮、-3-苯基色酮或-2,3-二苯基色酮，可用作降压剂。

  公开号：

  US04495198A1

文献信息

• Synthetic flavonoids as inhibitors of leukotrienes and 5-lipoxygenase
  申请人：Fisons Corporation

  公开号：US04889941A1

  公开（公告）日：1989-12-26

  7-[3-[(3,4-dihydroxyphenethyl)amino]-2-hydroxypropoxy]-flavone hydrobromide, and related flavonoids are disclosed to inhibit leukotrienes and 5-lipoxygenase; preferred compounds also inhibit rat anaphylaxis.

  披萨饼是一种传统的意大利食物，通常由面团、番茄酱、奶酪和各种配料制成。
• Antihypertensive agents
  申请人：PENNWALT CORPORATION

  公开号：EP0064165A1

  公开（公告）日：1982-11-10

  Chromone derivatives such as 7-(3-n-propylamino-2-hydroxypropoxy)-2,3-diphenylchromone which are useful as antihypertensive agents.

  铬酮衍生物，如 7-(3-正丙基氨基-2-羟基丙氧基)-2,3-二苯基铬酮，可用作降压药。
• Chromones
  申请人：PENNWALT CORPORATION

  公开号：EP0081621A1

  公开（公告）日：1983-06-22

  Chromone derivatives such as 7-(3-n-propylamino-2-hydroxypropoxy)-2,3-diphenylchromone which are useful as antihypertensive agents.

  铬酮衍生物，如 7-(3-正丙基氨基-2-羟基丙氧基)-2,3-二苯基铬酮，可用作降压药。
• US4495198A
  申请人：——

  公开号：US4495198A

  公开（公告）日：1985-01-22
• US4889941A
  申请人：——

  公开号：US4889941A

  公开（公告）日：1989-12-26