8-{3-[4-(2-hydroxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran | 152753-37-2

• 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: 8-{3-[4-(2-hydroxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran
• 英文别名: Rec 15/2802；N-(3-(4-(2-hydroxyphenyl)piperazin-1-yl)propyl)-3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxamide；8-{3-[4-(2-hydroxyphenyl)piperazinyl]propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran；8-{3-[4-(2-Hydroxyphenyl)-1-piperazinyl]propyl carbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran；N-[3-[4-(2-hydroxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide
• CAS: 152753-37-2
• 化学式: C₃₀H₃₁N₃O₄
• 分子量: 497.594
• InChiKey: NUFZAKVXJKBCKH-UHFFFAOYSA-N

物化性质

• 沸点：
  687.5±55.0 °C(predicted)
• 密度：
  1.250±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-{3-[4-(2-hydroxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran 在 吡啶 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid (3-{4-[2-(4-cyano-5-oxy-furazan-3-ylmethoxy)-phenyl]-piperazin-1-yl}-propyl)-amide
  参考文献：
  名称：

  New Potential Uroselective NO-Donor α₁-Antagonists

  摘要：

  A recent uroselective alpha(1)-adrenoceptor antagonist, REC15/2739, has been joined with nitrooxy and furoxan NO-donor moieties to give new NO-donor alpha(1)-antagonists. All the compounds studied proved to be potent and selective ligands of human cloned alpha(1a)-receptor subtype. Derivatives 6 and 7 were able to relax the prostatic portion of rat vas deferens contracted by (-)-noradrenaline because of both their alpha(1A)-antagonist and their NO-donor properties.

  DOI：

  10.1021/jm030825u
• 作为产物：
  描述：

  8-{3-[4-(2-methoxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到8-{3-[4-(2-hydroxyphenyl)-1-piperazinyl]-propylcarbamoyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran
  参考文献：
  名称：

  New Potential Uroselective NO-Donor α₁-Antagonists

  摘要：

  A recent uroselective alpha(1)-adrenoceptor antagonist, REC15/2739, has been joined with nitrooxy and furoxan NO-donor moieties to give new NO-donor alpha(1)-antagonists. All the compounds studied proved to be potent and selective ligands of human cloned alpha(1a)-receptor subtype. Derivatives 6 and 7 were able to relax the prostatic portion of rat vas deferens contracted by (-)-noradrenaline because of both their alpha(1A)-antagonist and their NO-donor properties.

  DOI：

  10.1021/jm030825u

文献信息

• Heterobicyclic compounds as antagogists of alpha-1 adrenergic and SHT1A receptors
  申请人：RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY

  公开号：EP0558245A1

  公开（公告）日：1993-09-01

  There are disclosed compounds of the general formula The heteroatom X is preferably oxygen, but may have other values. The group W is preferably a carbonyl group, but may have other values. The preferred heterocyclic ring is thus a 4-oxo-4H-1-benzopyran ring. This may have a wide range of R₂, R₃, R₆ and R₇ substituents. Y is a linking group, chosen from a wide range, but including -COO- , -CONH- , -O- , -SO₂- and -SO₂NH-. Z is an alkylene chain, and B is a complex amine. These compounds and their prodrugs, enantiomers, diastereoisomers, N-oxides and pharmaceutically acceptable salts are useful for the treatment of hypertension and urinary tract troubles associated with benign prostatic hypertrophy, and for the treatment of other diseases.

  已公开的化合物通式如下 杂原子 X 最好是氧，但也可以有其他值。基团 W 最好是羰基，但也可以有其他值。因此，优选的杂环是 4-氧代-4H-1-苯并吡喃环。它可以有多种 R₂、R₃、R₆ 和 R₇ 取代基。Y 是连接基团，可选范围很广，但包括-COO-、-CONH-、-O-、-SO₂- 和-SO₂NH-。Z 是亚烷基链，B 是复合胺。这些化合物及其原药、对映体、非对映异构体、N-氧化物和药学上可接受的盐类可用于治疗与良性前列腺肥大相关的高血压和尿路问题，也可用于治疗其他疾病。
• BENZOPYRAN DERIVATIVES
  申请人：RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.

  公开号：EP1222183B1

  公开（公告）日：2003-04-23
• US5403842A
  申请人：——

  公开号：US5403842A

  公开（公告）日：1995-04-04
• US5474994A
  申请人：——

  公开号：US5474994A

  公开（公告）日：1995-12-12
• US5605896A
  申请人：——

  公开号：US5605896A

  公开（公告）日：1997-02-25