4-(3,4-methylenedioxybenzyl)phthalazin-1(2H)-one | 365222-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(3,4-methylenedioxybenzyl)phthalazin-1(2H)-one
• 英文别名: 4-Benzo[1,3]dioxol-5-ylmethyl-2H-phthalazin-1-one；4-(1,3-benzodioxol-5-ylmethyl)-2H-phthalazin-1-one
• CAS: 365222-03-3
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: QZKXNYJIDCJSOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 4-(3,4-methylenedioxybenzyl)phthalazin-1(2H)-one 在 potassium carbonate 作用下， 生成 4-Benzo[1,3]dioxol-5-ylmethyl-2-butyl-2H-phthalazin-1-one
  参考文献：
  名称：

  Vasorelaxant activity of phthalazinones and related compounds

  摘要：

  Several series of dihydrostilbenamide, imidazo[2,1-a]isoindole, pyrimido[2,1-a]isoindole and phthalazinone derivatives were obtained and their vasorelaxant activity was measured on isolated rat aorta rings pre-contracted with phenylephrine (10(-5) M). Some phthalazinones attained, practically, the total relaxation of the organ at micromolar concentrations. For the most potent compound 9h (EC50 = 0.43 mu M) the affinities for alpha(1A), alpha(1B) and alpha(1D) adrenergic sub-receptors were determined. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.003
• 作为产物：
  描述：

  3-(benzo[d][1,3]dioxol-5-ylmethylene)isobenzofuran-1(3H)-one 在 肼 作用下， 以99%的产率得到4-(3,4-methylenedioxybenzyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  某些类胡萝卜素和相关杂环化合物的杀菌活性。

  摘要：

  我们已经评估了一些天然和半合成的二氢二苯乙烯类化合物和其他系列的二氢二苯乙烯酰胺，异吲哚，邻苯二氮酮，咪唑异吲哚和嘧啶异吲哚的几种化合物的杀菌活性。评估是在体外对利什曼原虫属的皮肤，粘膜皮肤和内脏菌株的培养物进行的。这些系列中最有效和选择性最大的化合物是二氢sti哌啶。

  DOI：

  10.1016/s0960-894x(01)00387-0

文献信息

• The imidazo[2,1-a]isoindole system. A new skeletal basis for antiplasmodial compounds
  作者：Esther del Olmo、Marlon Garcı́a Armas、Mª Inés Ybarra、Josè Luis López、Patricia Oporto、Alberto Giménez、Eric Deharo、Arturo San Feliciano

  DOI：10.1016/s0960-894x(03)00509-2

  日期：2003.8

  imidazo[2,1-a]isoindole and pyrimido[2,1-a]isoindole derivatives related to the natural dihydrostilbenoid isonotholaenic acid is reported. The evaluation was performed on cultures of F32 strain of Plasmodium falciparum and potent representative compounds were also evaluated in the ferriprotoporphyrin IX biomineralization inhibition test (FBIT). Compounds having the imidazo[2,1-a]isoindole skeleton

  报道了一些与天然二氢苯乙烯基异戊二烯酸相关的二氢苯乙烯基酰胺，邻苯二酮，咪唑并[2,1-a]异吲哚和嘧啶基[2,1-a]异吲哚衍生物的体外抗血浆活性。对恶性疟原虫的F32菌株的培养物进行了评估，并且还在铁原卟啉IX生物矿化抑制试验（FBIT）中评估了有效的代表性化合物。具有咪唑并[2，1-a]异吲哚骨架的化合物活性最高，该组中的一种化合物与氯喹一样有效，但通过抑制血红素生物矿化的机制起作用。
• Leishmanicidal activity of some stilbenoids and related heterocyclic compounds
  作者：Esther del Olmo、Marlon Garcı́a Armas、Jose Luis López-Pérez、Victoria Muñoz、Eric Deharo、Arturo San Feliciano

  DOI：10.1016/s0960-894x(01)00387-0

  日期：2001.8

  the leishmanicidal activity of some natural and semisynthetic dihydrostilbenoids and several compounds of other series of dihydrostilbamides, isoindoles, phthalazinones, imidazoisoindoles and pyrimidoisoindoles. The evaluation was performed in vitro, on cultures of cutaneous, mucocutaneous and visceral strains of Leishmania spp. The most potent and selective compounds of these series were the dihydrostilbene

  我们已经评估了一些天然和半合成的二氢二苯乙烯类化合物和其他系列的二氢二苯乙烯酰胺，异吲哚，邻苯二氮酮，咪唑异吲哚和嘧啶异吲哚的几种化合物的杀菌活性。评估是在体外对利什曼原虫属的皮肤，粘膜皮肤和内脏菌株的培养物进行的。这些系列中最有效和选择性最大的化合物是二氢sti哌啶。
• Anti-HIV activity of stilbene-related heterocyclic compounds
  作者：Luis M. Bedoya、Esther del Olmo、Rocío Sancho、Bianca Barboza、Manuela Beltrán、Ana E. García-Cadenas、Sonsoles Sánchez-Palomino、José L. López-Pérez、Eduardo Muñoz、Arturo San Feliciano、José Alcamí

  DOI：10.1016/j.bmcl.2006.04.087

  日期：2006.8

  Viral transcription has not been routinely targeted in the development of new antiviral drugs. This crucial step of the viral cycle depends on the concerted action of cellular and viral proteins such as NF-kappa B and Tat. In the present study, stilbene-related heterocyclic compounds including benzalphthalide, phthalazinone, imidazoindole and pyrimidoisoindole derivatives are tested for their anti-HIV activity. Original assays based on recombinant viruses were used to evaluate HIV replication inhibition and stably transfected cell lines were used to evaluate inhibition of Tat and NF-kappa B proteins. Some of the stilbene-related heterocyclic compounds analysed displayed anti-HIV activity through interference with NF-kappa B and Tat function. Moreover, compounds inhibiting both targets displayed a stronger activity on viral replication. (c) 2006 Elsevier Ltd. All rights reserved.
• PHTHALAZINONE DERIVATIVES
  申请人：Kudos Pharmaceuticals Limited

  公开号：EP1330442B1

  公开（公告）日：2011-01-19
• US7750006B2
  申请人：——

  公开号：US7750006B2

  公开（公告）日：2010-07-06