1-chloro-4-methyl-9H-xanthen-9-one | 55950-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-chloro-4-methyl-9H-xanthen-9-one
• 英文别名: 1-Chloro-4-methyl-9-xanthenone；1-chloro-4-methylxanthen-9-one
• CAS: 55950-72-6
• 化学式: C₁₄H₉ClO₂
• 分子量: 244.677
• InChiKey: MDTREROSCDWIHF-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  397.3±42.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-4-methyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 4-(Bromomethyl)-1-chloroxanthen-9-one
  参考文献：
  名称：

  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo

  摘要：

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.

  DOI：

  10.1021/jm00124a012
• 作为产物：
  描述：

  邻氯苯甲酸钾 在 硫酸 、 铜 作用下， 生成 1-chloro-4-methyl-9H-xanthen-9-one
  参考文献：
  名称：

  Mauss, Chemische Berichte, 1948, vol. 81, p. 19,26

  摘要：

  DOI：

文献信息

• Multitarget Therapeutic Leads for Alzheimer’s Disease: Quinolizidinyl Derivatives of Bi- and Tricyclic Systems as Dual Inhibitors of Cholinesterases and β-Amyloid (Aβ) Aggregation
  作者：Michele Tonelli、Marco Catto、Bruno Tasso、Federica Novelli、Caterina Canu、Giovanna Iusco、Leonardo Pisani、Angelo De Stradis、Nunzio Denora、Anna Sparatore、Vito Boido、Angelo Carotti、Fabio Sparatore

  DOI：10.1002/cmdc.201500104

  日期：2015.6

  displayed inhibitory activity on both AChE and BChE and on the spontaneous aggregation of β‐amyloid. In most cases, IC50 values were in the low micromolar and sub‐micromolar range, but some compounds even reached nanomolar potency. The time course of amyloid aggregation in the presence of the most active derivative (IC50=0.84 μM) revealed that these compounds might act as destabilizers of mature fibrils

  在能够维持或恢复细胞蛋白稳态并抑制β-淀粉样蛋白（Aβ）寡聚化的化合物模型上设计了阿尔茨海默氏病的多靶点治疗药物。测试了37种噻吨酮9‐1，黄嘌呤‐9‐1，萘酚和蒽醌衍生物对Aβ（1-40）聚集的直接抑制作用以及对电鳗乙酰胆碱酯酶（eeAChE）和马血清丁酰胆碱酯酶（ hsBChE）。这些化合物的特征是与各种双环和三环（杂）芳族体系连接的碱性侧链（主要是喹啉亚二烷基烷基）。除极少数例外，这些化合物均对AChE和BChE以及对β-淀粉样蛋白的自发聚集均具有抑制活性。在大多数情况下，IC 50值在低微摩尔和亚微摩尔范围内，但有些化合物甚至达到了纳摩尔效价。在最活跃的衍生物的存在淀粉状蛋白聚集的时间过程（IC 50 = 0.84μ中号）揭示了这些化合物还不如成熟的纤维，而不是原纤维化的单纯的抑制剂的去稳定作用。许多化合物以相似的效力抑制胆碱酯酶和Aβ聚集中的一种或两种，这是可能开发出具有多目标作
• Benzo and benzothiopyranoindazole N-oxides
  申请人：Parke, Davis & Company

  公开号：US03963740A1

  公开（公告）日：1976-06-15

  2H(1)Benzothiopyrano[4,3,2-cd]indazole N-oxides, 2H(1)benzopyrano[4,3,2-cd]indazole N-oxides and acid addition salts thereof are disclosed. These compounds can be produced by oxidation of the corresponding amines with oxidizing agents capable of forming an N-oxide derivative. The compounds are parasiticidal agents useful in the treatment of schistosome infections.

  本发明公开了2H(1)苯并噻吩并[4,3,2-cd]吲哚N-氧化物，2H(1)苯并噻吩并[4,3,2-cd]吲哚N-氧化物及其酸盐加成物。这些化合物可以通过使用能够形成N-氧化物衍生物的氧化剂氧化相应的胺来制备。这些化合物是治疗血吸虫感染的寄生虫杀虫剂。
• Anti-α-Glucosidase and Antiglycation Activities of α-Mangostin and New Xanthenone Derivatives: Enzymatic Kinetics and Mechanistic Insights through In Vitro Studies
  作者：Francine Medjiofack Djeujo、Valeria Francesconi、Maddalena Gonella、Eugenio Ragazzi、Michele Tonelli、Guglielmina Froldi

  DOI：10.3390/molecules27020547

  日期：——

  intestinal hydrolase that catalyzes the cleavage of oligosaccharides into glucose molecules, promoting the postprandial glycemic peak. Antiglycation activity was evaluated using the BSA assay, while antioxidant capacity was detected with the ORAC assay. The inhibition of α-glucosidase activity was studied with multispectroscopic methods along with inhibitory kinetic analysis. α-Mangostin and synthetic compounds

  糖尿病的特点是慢性高血糖，促进活性氧的形成，引起严重的氧化应激。此外，长时间的高血糖会导致糖基化反应，并形成 AGEs，从而导致慢性炎症状态。本研究旨在评估 α-山竹素和四种合成的呫吨酮衍生物对糖化和氧化过程的抑制活性，以及​​对 α-葡萄糖苷酶的抑制活性，α-葡萄糖苷酶是一种肠道水解酶，可催化寡糖裂解为葡萄糖分子，促进餐后血糖峰值。使用 BSA 测定法评估抗糖化活性，而使用 ORAC 测定法检测抗氧化能力。用多光谱方法以及抑制动力学分析研究了对α-葡萄糖苷酶活性的抑制。25 µM 的 α-Mangostin 和合成化合物可减少 AGEs 的产生，而 α-葡萄糖苷酶活性仅被天然化合物抑制。α-Mangostin 通过可逆的混合型拮抗作用在微摩尔范围内以浓度依赖性方式降低酶活性。圆二色性揭示了α-葡萄糖苷酶二级结构的重排，α-螺旋和无规卷曲的含量增加，β-折叠和β-转角成分减少。数据突出了α
• Reactions with Halogen Substituted Xanthones. II¹
  作者：Ahmed Mustafa、Wafia Asker、Mohamed Ezz El-Din Sobhy

  DOI：10.1021/ja01624a051

  日期：1955.10
• DE919107
  申请人：——

  公开号：——

  公开（公告）日：——