2-(9-Oxoxanthen-4-yl)acetonitrile | 54182-77-3

• 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: 2-(9-Oxoxanthen-4-yl)acetonitrile
• CAS: 54182-77-3
• 化学式: C₁₅H₉NO₂
• 分子量: 235.242
• InChiKey: JXQMINJYAYBFDB-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  468.4±34.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(9-Oxoxanthen-4-yl)acetonitrile 在 硫酸 、 水 、 溶剂黄146 作用下， 生成 2-(9-氧代氧杂蒽-4-基)乙酸
  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：

  4-methylxanthen-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 、 乙醇 、 水 为溶剂， 生成 2-(9-Oxoxanthen-4-yl)acetonitrile
  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

文献信息

• [EN] XANTHONE DERIVATIVES, UV PROTECTIVE COMPOSITION CONCENTRATE, METHOD OF PREPARATION OF UV PROTECTIVE COMPOSITION CONCENTRATE, USE OF UV PROTECTIVE COMPOSITION CONCENTRATE AND COSMETIC UV PROTECTIVE PRODUCT<br/>[FR] DÉRIVÉS DE XANTHONE, CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV, PROCÉDÉ DE PRÉPARATION DE CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV, UTILISATION D'UN CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV ET PRODUIT COSMÉTIQUE DE PROTECTION CONTRE LES UV
  申请人：UNIV JAGIELLONSKI

  公开号：WO2021215943A1

  公开（公告）日：2021-10-28

  The first object of the invention is a xanthone derivative described by formula (I) where R1 is a substituent selected from the group comprising: hydrogen or alkoxy group; R2 is a substituent selected from the group comprising methylcinnamoyl, phenylpenta-2,4- dienenitrile, cyanoethenylphenyl or cyanoethenylalkyl substituent, wherein the phenyl ring is substituted with R3 selected from the group consisting of: hydrogen, alkoxy substituent or halide atom. The second objection of the invention is a UV protective composition concentrate containing the xanthone derivative described by the formula (I). The third object of the invention is a method for the preparation of a UV protective composition concentrate. The next object of the invention is the use of a UV protective composition concentrate for the production of UV protective cosmetic products. Yet another object of the invention is a cosmetic UV protective product.

  该发明的第一个对象是一种黄酮衍生物，其化学式为（I），其中R1是从包括：氢或烷氧基的基团中选择的取代基；R2是从包括：甲基肉桂酰基、苯基戊-2,4-二烯腈基、氰基乙烯基苯基或氰基乙烯基取代基中选择的取代基，其中苯环与R3选择自包括：氢、烷氧基取代基或卤素原子的基团。该发明的第二个对象是一种含有上述化学式（I）所述黄酮衍生物的紫外线防护组合物浓缩物。该发明的第三个对象是一种制备紫外线防护组合物浓缩物的方法。该发明的下一个对象是利用紫外线防护组合物浓缩物生产紫外线防护化妆品产品。该发明的另一个对象是一种化妆用紫外线防护产品。
• Compounds having antitumour and antibacterial properties
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0278176B1

  公开（公告）日：1994-03-09
• NAKANISHI MICHIO; OE TAKANORI; TSURUDA MINEO; MATSUO HIROSHI; SAKURAGI SH+, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR. <YKKZ-AJ>, 1976, 96+
  作者：NAKANISHI MICHIO、 OE TAKANORI、 TSURUDA MINEO、 MATSUO HIROSHI、 SAKURAGI SH+

  DOI：——

  日期：——
• US5281620A
  申请人：——

  公开号：US5281620A

  公开（公告）日：1994-01-25
• Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、Stephen B. Calveley、William A. Denny

  DOI：10.1021/jm00124a012

  日期：1989.4

  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.