羟基甲基氧丙基苯并吡喃酮 | 28955-30-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 羟基甲基氧丙基苯并吡喃酮
• 英文名称: Cassiachromone
• 英文别名: 2-(7-hydroxy-2-methyl-4-oxo-4H-chromen-5-yl) acetic acid；7-hydroxy-2-methyl-5-(2-oxopropyl)-4H-chromen-4-one；5-acetonyl-7-hydroxy-2-methylchromone；7-hydroxy-2-methyl-5-(2-oxo-propyl)-chromen-4-one；7-hydroxy-2-methyl-5-(2-oxopropyl)chromen-4-one
• CAS: 28955-30-8
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: YMCXDPKFRCHLPK-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C
• 沸点：
  444.7±45.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  存放在2-8℃环境中，应保持干燥并密封。

制备方法与用途

Cassiachromone可以从Cassia siamea中分离得到。

反应信息

• 作为反应物：
  描述：

  羟基甲基氧丙基苯并吡喃酮 在 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 26.5h， 生成 7,7’-Bis(methoxymethoxy)-12,12’-bis(1,3-dioxolan-2-yl)-4’-(tert-butyldimethylsilyloxy)-chrobisiamone A
  参考文献：
  名称：

  BIOMIMETIC SYNTHESIS OF CHROBISIAMONE A FROM CASSIA sIAMEA

  摘要：

  Chrobisiamone A (1), an unique chromone dimer from leaves of Cassia siamea Lam. (Leguminosae), was synthesized from 5-acetonyl-7-hydroxy-2-methylchromone (2) in 4 steps through biomimetic Michael addition.

  DOI：

  10.3987/com-12-s(n)111
• 作为产物：
  描述：

  3a,4-dihydro-3a,8-dihydroxy-2,5-dimethyl-1,4-dioxaphenalene 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以32%的产率得到羟基甲基氧丙基苯并吡喃酮
  参考文献：
  名称：

  Transformation of barakol into cassiarins A, B, and their derivatives

  摘要：

  Three semi-syntheses of cassiarins A and B from barakol are described. The route involving use of anhydrobarakol chloride as a key precursor showed most versatility because it does not require an expensive catalyst, protection of functional groups, or chromatographic purification, allowing the facile preparation of eight cassiarin derivatives. The photophysical properties of these compounds were characterized by UV-vis absorption, fluorescence emission, and quantum yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.053

文献信息

• Biomimetic Total Syntheses of Cassiarins A and B
  作者：Yuan-Shan Yao、Zhu-Jun Yao

  DOI：10.1021/jo801017b

  日期：2008.7.1

  Total syntheses of cassiarins A and B have been efficiently accomplished using a common strategy with biomimetic considerations. Key reactions involved in this synthesis include a Negishi-type coupling, a Ag(I)-promoted formation of the tricyclic 8H-pyrano[2,3,4-de]chromen-8-one core, and a sequential amine-condensation and cyclization. Three new analogues of cassiarin A bearing different substituents

  使用仿生学的通用策略已有效地完成了卡西林A和B的总合成。参与该合成的关键反应包括Negishi型偶联，Ag（I）促进的三环8 H-吡喃并[2,3,4- de ] chromen -8-one核的形成以及顺序的胺缩合和环化。从同一中间体平行合成了三个新的肉桂素A类似物，它们在C-11位置带有不同的取代基。另外，从相应的化学等效前体获得了对关键三环核心和卡西林A和B的另外两个转化。
• Cassiadinine, a chromone alkaloid and (+)-6-hydroxy-mellein, a dihydroisocoumarin from Cassia siamea
  作者：Kshetra M. Biswas、Haimanti Mallik

  DOI：10.1016/s0031-9422(00)81245-5

  日期：1986.1

  Abstract Cassiadinine, a new chromone alkaloid and (+)-6-hydroxymellein, a new dihydroisocoumarin isomer have been isolated together with three triterpenoids, cycloart-23-en-3β,25-diol, friedelin and betulin, a chromone derivative, 5-acetonyl-7-hydroxy-2-methylchromone and γ-sitosterol from the petrol and chloroform extracts of the flowers of Cassia siamea .

  摘要 Cassiadinine，一种新的色酮生物碱和 (+)-6-hydroxymellein，一种新的二氢异香豆素异构体，以及三种三萜类化合物，cycloart-23-en-3β,25-diol、 Friedelin 和白桦脂醇，一种色酮衍生物，5-来自桂皮花的汽油和氯仿提取物中的丙酮基-7-羟基-2-甲基色酮和γ-谷甾醇。
• Synthesis and structure–activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity
  作者：Hiroshi Morita、Yuichiro Tomizawa、Jun Deguchi、Tokio Ishikawa、Hiroko Arai、Kazumasa Zaima、Takahiro Hosoya、Yusuke Hirasawa、Takayuki Matsumoto、Katsuo Kamata、Wiwied Ekasari、Aty Widyawaruyanti、Tutik Sri Wahyuni、Noor Cholies Zaini、Toshio Honda

  DOI：10.1016/j.bmc.2009.10.013

  日期：2009.12

  Cassiarin A 1, a tricyclic alkaloid, isolated from the leaves of Cassia siamea (Leguminosae), shows powerful antimalarial activity against Plasmodium falciparum in vitro as well as P. berghei in vivo, which may be valuable leads for novel antimalarials. Interactions of parasitized red blood cells (pRBCs) with endothelium in aorta are especially important in the processes contribute to the pathogenesis

  从决明子（Lesiaminosae）的叶子中分离出的三环生物碱Cassiarin A 1对恶性疟原虫和体内的伯氏疟原虫具有强大的抗疟疾活性，这可能是新型抗疟疾的有价值的线索。在导致严重疟疾发病机理的过程中，被寄生的红细胞（pRBC）与主动脉内皮的相互作用尤为重要。一氧化氮（NO）减少了pRBC粘附于血管内皮的受体/粘附分子的内皮表达，并降低了pRBC对血管内皮的细胞粘附。决明A 1表现出对大鼠主动脉环的血管舒张活性，这可能与一氧化氮的产生有关。一系列的羟基和氮取代的衍生物和的脱衍生物的1已被合成为具有针对有效的抗疟药恶性疟原虫具有血管舒张活性，这可以减少的pRBC的细胞粘连至血管内皮。决明子A 1在体外表现出有效的抗疟疾活性和高选择性指数，表明没有任何取代基的羟基和氮原子的存在对于显示抗疟疾活性可能很重要。相对于决明子A，甲氧基衍生物显示出更强的血管舒张活性，尽管它并未显示出对恶性疟原虫抑
• Chrobisiamone A, a new bischromone from Cassia siamea and a biomimetic transformation of 5-acetonyl-7-hydroxy-2-methylchromone into cassiarin A
  作者：Shiori Oshimi、Yuichiro Tomizawa、Yusuke Hirasawa、Toshio Honda、Wiwied Ekasari、Aty Widyawaruyanti、Marcellino Rudyanto、Gunawan Indrayanto、Noor Cholies Zaini、Hiroshi Morita

  DOI：10.1016/j.bmcl.2008.05.041

  日期：2008.7

  A new bischromone, chrobisiamone A (1) with an antiplasmodial activity has been isolated from the leaves of Cassia siamea and the structure was elucidated by 2D NMR analysis. Cyclization of 5-acetonyl-7-hydroxy-2-methylchromone (2) in the presence of ammonium acetate resulted in generation of cassiarin A (3) with an unprecedented tricyclic skeleton, supporting a biogenetic pathway proposed for 3.

  从决明子的叶片中分离出了一种具有抗疟原虫活性的新双色酮，Chrobisiamone A（1），并通过2D NMR分析阐明了其结构。在乙酸铵存在下将5-丙酮基-7-羟基-2-甲基色酮（2）环化导致生成具有空前三环骨架的决明子A（3），支持为3提出的生物遗传途径。
• IL-8 receptor ligands - drugs for inflammatory and autoimmune diseases
  申请人：——

  公开号：US20020123483A1

  公开（公告）日：2002-09-05

  The invention provides therapeutic and biological uses of chemokine-receptor-binding compounds (including chemokine receptor ligands such as chemokine receptor agonists or antagonists), such as benzopyrone derivatives, including uses in the treatment of disease states mediated by chemokines. The relevant chemokine may for example be interleukin-8 (IL-8), and the relevant chemokine receptors may for example be corresponding chemokine receptors (CXCR-1 and/or CXCR-2). In other aspects, the invention provides corresponding pharamaceutical compositions and therapeutic methods. In one aspect, for example, the invention provides for the use of [7-[benzopyrone-5′(3′-amino)-thiazole]-phenylalanine-benyl ester in the treatment of disease.

  本发明提供了趋化因子受体结合化合物（包括趋化因子受体配体，如趋化因子受体激动剂或拮抗剂），如苯并吡喃酮衍生物的治疗和生物学用途，包括用于治疗由趋化因子介导的疾病状态。相关的趋化因子例如可以是白细胞介素-8（IL-8），相关的趋化因子受体例如可以是相应的趋化因子受体（CXCR-1和/或CXCR-2）。在其他方面，本发明提供了相应的药物组合物和治疗方法。例如，在一个方面，本发明提供了[7-[苯并吡喃酮-5′（3′-氨基）-噻唑]-苯丙氨酸苄酯在治疗疾病中的用途。