(2-hydroxy-3,4-dimethoxyphenyl)(2-methoxyphenyl)methanone | 147188-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-hydroxy-3,4-dimethoxyphenyl)(2-methoxyphenyl)methanone
• 英文别名: 3,4-Dimethoxy-2-hydroxy-2'-methoxybenzophenone；(2-hydroxy-3,4-dimethoxyphenyl)-(2-methoxyphenyl)methanone
• CAS: 147188-08-7
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: LVARVEKCGWPHPU-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  458.7±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-hydroxy-3,4-dimethoxyphenyl)(2-methoxyphenyl)methanone 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 60.0h， 生成 pyranoxanthone
  参考文献：
  名称：

  Insights into the In Vitro Antitumor Mechanism of Action of a New Pyranoxanthone

  摘要：

  Naturally occurring xanthones have been documented as having antitumor properties, with some of them presently undergoing clinical trials. In an attempt to improve the biological activities of dihydroxyxanthones, prenylation and other molecular modifications were performed. All the compounds reduced viable cell number in a leukemia cell line K‐562, with the fused xanthone 3,4‐dihydro‐12‐hydroxy‐2,2‐dimethyl‐2H,6H‐pyrano[3,2‐b]xanthen‐6‐one (5) being the most potent. The pyranoxanthone 5 was particularly effective in additional leukemia cell lines (HL‐60 and BV‐173). Furthermore, the pyranoxanthone 5 decreased cellular proliferation and induced an S‐phase cell cycle arrest. In vitro, the pyranoxanthone 5 increased the percentage of apoptotic cells which was confirmed by an appropriate response at the protein level (e.g., PARP cleavage). Using a computer screening strategy based on the structure of several anti‐ and pro‐apoptotic proteins, it was verified that the pyranoxanthone 5 may block the binding of anti‐apoptotic Bcl‐xL to pro‐apoptotic Bad and Bim. The structure‐based screening revealed the pyranoxanthone 5 as a new scaffold that may guide the design of small molecules with better affinity profile for Bcl‐xL.

  DOI：

  10.1111/j.1747-0285.2010.00978.x
• 作为产物：
  描述：

  邻甲氧基苯甲酸 在 三氯化铝 、 草酰氯 作用下， 以 乙醚 、 苯 为溶剂， 反应 10.0h， 生成 (2-hydroxy-3,4-dimethoxyphenyl)(2-methoxyphenyl)methanone
  参考文献：
  名称：

  γ-吡喃酮化合物。IV：单和双氧合的氧杂蒽和氧杂氧丙醇胺的合成和抗血小板作用。

  摘要：

  由二苯甲酮前体合成黄原醇，单和双氧合的氧杂蒽，以及1,3-，2,3-，3,4-，3,5-，1,6-，2,6-和3,6-二氧合的氧杂蒽由Friedel-Crafts酰化，然后进行碱催化的环化反应以消除甲醇。3-羟-吨酮，黄酮醇，2,3-二羟x吨酮二乙酸盐和3,4-二羟di吨酮及其二乙酸盐对花生四烯酸和胶原诱导的聚集表现出有效的抗血小板作用。3,5-二羟基黄酮及其双乙酸盐，1,6-二甲氧基黄酮和3,6-二羟基黄酮及其二乙酸盐对花生四烯酸诱导的聚集表现出有效的抗血小板作用。

  DOI：

  10.1002/jps.2600820103

文献信息

• New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms
  作者：Ye' Zaw Phyo、Joana Teixeira、Maria Elizabeth Tiritan、Sara Cravo、Andreia Palmeira、Luís Gales、Artur M.S. Silva、Madalena M.M. Pinto、Anake Kijjoa、Carla Fernandes

  DOI：10.1002/chir.23142

  日期：2020.1

  the development of new chiral stationary phases (CSPs) for liquid chromatography (LC) based on chiral derivatives of xanthones (CDXs). Based on the most promising CDX selectors, 12 new CSPs were successfully prepared starting from suitable functionalized small molecules including xanthone and benzophenone derivatives. The chiral selectors comprising one, two, three, or four chiral moieties were covalently

  最近，我们报道了基于氧杂蒽酮（CDXs）的手性衍生物的液相色谱（LC）的新手性固定相（CSP）的开发。基于最有前途的CDX选择器，成功地从合适的功能化小分子（包括one吨酮和二苯甲酮衍生物）制备了12种新的CSP。将包含一个，两个，三个或四个手性部分的手性选择剂共价键合到色谱载体上，并进一步填充到LC不锈钢柱（150×2.1 mm ID）中。使用不同种类的手性化合物通过LC评估了新CSP的对映选择性。在评估新的CSP时观察到了对映体分离某些CDX的特异性。除了，通过使用分子对接方法的计算研究对手性识别机理进行了评估，这与色谱参数相符。X射线分析用于建立手性选择器3D结构。
• Synthesis, Biological Evaluation, and In Silico Studies of Novel Aminated Xanthones as Potential p53-Activating Agents
  作者：Agostinho Lemos、Ana Sara Gomes、Joana B. Loureiro、Pedro Brandão、Andreia Palmeira、Madalena M. M. Pinto、Lucília Saraiva、Maria Emília Sousa

  DOI：10.3390/molecules24101975

  日期：——

  p53-activating agent through inhibition of interaction with MDM2. Xanthone 37 inhibited the growth of human colon adenocarcinoma HCT116 cell lines in a p53-dependent manner. The growth inhibitory effect of xanthone 37 was associated with the induction of G1-phase cell cycle arrest and increased protein expression levels of p53 transcriptional targets. These results demonstrated the potential usefulness

  呫吨酮支架已被视为一种有吸引力的化学工具，用于寻找具有抗肿瘤活性的生物活性分子，特别是两种呫吨酮衍生物，12-羟基-2,2-二甲基-3,4-二氢-2H,6H-吡喃 [3] ,2-b]xanthen-6-one (4) 和 3,4-dimethoxy-9-oxo-9H-xanthene-1-carbaldehyde (5)，被描述为鼠双分钟 2 (MDM2)-p53 抑制剂和分别是 TAp73 激活剂。呫吨酮 5 被用作构建带有所述 MDM2-p53 抑制剂化学部分的 3,4-双氧合呫吨酮文库的起点。成功合成了 11 种胺化氧杂蒽酮，并使用基于酵母细胞的测定对其破坏 MDM2-p53 相互作用的能力进行了初步筛选。通过这种方法，通过抑制与 MDM2 的相互作用，氧杂蒽酮 37 被鉴定为推定的 p53 激活剂。Xanthone 37 以 p53 依赖性方式抑制人结肠腺癌 HCT116 细胞系的生长。氧杂蒽酮
• Synthesis and pharmacological activity of a series of novel xanthone
  申请人：National Science Council

  公开号：US05495005A1

  公开（公告）日：1996-02-27

  A compound, and salts thereof, represented by either formula I or formula II below: (1) Formula I: ##STR1## wherein substituents R.sub.1 -R.sub.7 can be, independently, hydrogen, hydroxy group, C.sub.1-6 alkyl(oxy) group, acetyl ester, or C.sub.1-12 alkyl propanolamine; at least three but no more than four of the substituents are alkyl(oxy) group, hydroxyl group or acetyl ester; no more than one of the substituents can be C.sub.1-12 alkyl propanolamines; R.sub.1, R.sub.3, R.sub.7 cnnnot all be hydroxy groups at the same time; and R.sub.6 is either an hydroxy group or an oxygen-containing glucose. (2) Formula II: ##STR2## wherein substituents R.sub.1 -R.sub.9 can be, indenpendently, hydrogen, hydroxy group and C.sub.1-6 alkyl(oxy) group; and no more then four of the substituents can be methoxy group, hydroxy group, or acetyl ester. These compounds were tested to be capable of inhibiting platelet aggregation, atrioventricular conduction, and calcium influx in myocardiac cells.

  以下是公式I或公式II表示的化合物及其盐： （1）公式I：##STR1## 其中取代基R.sub.1-R.sub.7可以是独立的氢、羟基、C.sub.1-6烷基（氧）基、乙酰酯或C.sub.1-12烷基丙醇胺；至少三个但不超过四个取代基是烷基（氧）基、羟基或乙酰酯；最多只有一个取代基可以是C.sub.1-12烷基丙醇胺；R.sub.1，R.sub.3，R.sub.7不能同时都是羟基；R.sub.6是羟基或含氧葡萄糖。 （2）公式II：##STR2## 其中取代基R.sub.1-R.sub.9可以是独立的氢、羟基和C.sub.1-6烷基（氧）基；最多只有四个取代基可以是甲氧基、羟基或乙酰酯。这些化合物被证明能够抑制血小板聚集、房室传导和心肌细胞中的钙离子流入。
• Compounds for the treatment of hepatoma
  申请人：National Science Council

  公开号：US05741813A1

  公开（公告）日：1998-04-21

  Compounds of general Formula I in which the substituents of R.sub.1 -R.sub.7 are hydrogen, hydroxy group, C.sub.1-6 alkyl group, C.sub.1-6 alkoxy group, or epoxypropoxy, but at the most, six of the substituents can simultaneously be hydrogen, methoxy group, or hydroxy group, or epoxypropoxy group for activity against hepatoma. There are also described processes for the preparation of the novel compounds and useful intermediates. Substitute benzophenones are described.

  通式I的化合物中，R.sub.1-R.sub.7的取代基为氢、羟基、C.sub.1-6烷基、C.sub.1-6烷氧基或环氧丙氧基，但最多只有六个取代基可以同时为氢、甲氧基或羟基，或环氧丙氧基，以用于肝癌的活性。还描述了制备新化合物和有用中间体的过程。还描述了取代苯酮。
• Bromoalkoxyxanthones as promising antitumor agents: Synthesis, crystal structure and effect on human tumor cell lines
  作者：Emília Sousa、Ana Paiva、Nair Nazareth、Luis Gales、Ana M. Damas、Maria S.J. Nascimento、Madalena Pinto

  DOI：10.1016/j.ejmech.2009.04.011

  日期：2009.9

  In a study involving the synthesis of bis-intercalators, a bisxanthone and a minor product, 1-(6-bromohexyloxy)-xanthone were obtained. Although no capacity to inhibit the growth of human tumor cell lines was observed for the bisxanthone, the bromoalkoxyxanthone revealed this biological activity. In light of these results bromoalkylation of 3,4-dihydroxyxanthone furnished two bromohexyloxyxanthones that were investigated for their effect on the in vitro growth of human tumor cell lines MCF-7 (ER+, breast), MDA-MB-231 (ER-, breast), NCI-H460 (non-small lung), and SF-268 (central nervous system). The X-ray structure of 1-(6-bromohexyloxy)-xanthone revealed that the xanthone skeleton remains essentially planar forming a dihedral angle of 61.3(2)degrees with the 6-bromohexyl side chain. These results revealed bromoalkoxyxanthones as interesting scaffolds to look for potential anticancer drugs. (C) 2009 Elsevier Masson SAS. All rights reserved.